best time to visit woodstock vermont in the fall

New England Wanderlust

Fall , Spring , Summer , Vermont , Winter  ·  September 15, 2022

27 Wonderful Things To Do In Woodstock, VT In Every Season (2024)

Woodstock is one of my absolute favorite towns in Vermont to visit, regardless of the season. It’s packed with so much small town, New England charm at every turn, and it offers such a fun variety of things to do. Throw in amazing restaurants and picturesque covered bridges, it’s also one of the best places to visit in New England .

If you’re trying to plan your first trip to Woodstock, you’re in the right place. I’ve visited Woodstock in all the seasons, and I’m thrilled to share with you my top things to do in this cute little town. With that, let’s jump in!

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Is Woodstock, VT Worth Visiting?

Absolutely, and if you’re looking to visit one of the most charming towns in Vermont, Woodstock is the perfect choice. In the main village, you’ll find a lovely covered bridge, adorable shops, awesome cafes and eateries, a general store, beautiful houses and side streets. All of these things combined will have you feeling like you’re the star of your very own Hallmark movie.

Best Things To Do In Woodstock, VT

Below is my list of all the best things to do in Woodstock, VT. To help you keep organized, I’ve divided some of them out by season, and also included additional things that are worth doing nearby during your visit.

1. Visit The Covered Bridges

New England is one of the best places to see the adorable little covered bridges, and Vermont is home to over 100 of them. Here in Woodstock, you’ll be able to see three! The most famous one in Woodstock is the Middle Covered Bridge, which is located right in the village.

A few minutes outside of the village, you can also see Taftsville Covered Bridge and Lincoln Covered Bridge. You’ll want to drive to these, as they’re not easily walkable from town, but they’re definitely worth venturing over to.

2. Stroll Through The Shops & Town Green

Woodstock has one of the most beautiful little downtown areas in New England, and it’s all centered around the The Green. Here, you’ll find access to Middle Covered Bridge, as well as all the shops and restaurants, and lots of beautiful side streets to wander.

While strolling around town, I suggest popping into the Vermont Flannel Company , the Yankee Bookshop , F.H. Gillinghams , and Woody’s Mercantile . When exploring Woodstock by car, I definitely suggest you make a stop at Farmhouse Pottery , too. Not only is the store beautiful, but you can watch some of the artisans at work, or even take a wheel workshop (more on that later, though).

3. Have Fun At Billings Farm & Museum

One of the most fun places to visit in Woodstock, VT is to head to Billings Farm & Museum , which is only about a mile outside of town center. During your visit to this 200-acre working dairy farm, you’ll be able to see the historic barns on the property, take in gorgeous rural landscapes, enjoy a scenic walk through their gardens and nature path, pet the animals in the barn, and even take a wagon ride around the farm.

Be sure to swing by the Farmhouse Cafe for ice cream, drinks and snacks. You can also pick up their freshly-made cheeses and butter to take home with you.

4. Explore The Marsh-Billings-Rockefeller Historical Site

The question to ask yourself while visiting the Marsh-Billings-Rockefeller Historical Site is – what can’t I do here? This is honestly such a gem, and one of the best attractions in Woodstock, VT. Here, you’ll be able to take tours of the historic mansions and grounds, hike 20 miles of nature trails, take in the beautiful gardens, go on a horseback ride, stroll through the Mount Tom Forest, and so much more.

If you enjoy serene nature walks, I highly suggest you visit. The trails through the Mount Tom Forest are really beautiful and relaxing, and some of the views along the hiking trails are truly stunning (especially in the fall!). But the best part? It’s completely free to explore on your own (there is a fee for guided tours).

5. Hike To The Top Of Mount Tom

For a bird’s eye view of town, one of the best things to do in Woodstock, VT is to hike up to the top of Mount Tom. The trailhead can be found inside the Marsh-Billings-Rockefeller Historical Site, and the hike is about 5.5 miles round trip. The elevation gain is fairly moderate, so it isn’t too challenging, but it will require a bit of a workout nonetheless.

Once you reach the top, you’ll be rewarded with really great views of Woodstock from above, and since you’re already on the trail system, you can easily connect to other hikes if you wanted to make a day of it.

6. Learn How To Handle A Falcon

If you’re interested in wildlife, one of the coolest experiences to have in Woodstock, VT is an experience with New England Falconry . This experience is the very first tour of its kind to be allowed in the U.S., and is led by a Master Falconer. You’ll learn all about these beautiful animals, as well as conservation efforts and their history. And of course, get your chance at handling one of the trained falcons.

Depending on the experience you choose, you may also get the chance to handle an owl, which is an incredibly memorable experience.

7. Taste Local Cheeses and Syrups At Sugarbush Farm

No trip to Woodstock is complete until you’ve visited Sugarbush Farms to sample some of their own cheeses and maple syrups, all of which are made right on the farm. Located only a short 15 minute drive from the main village, not only is the surrounding farmland beautiful, but you’ll get to nibble on samples of their 15 different cheeses, taste their maple syrups, and take a self-guided tour through their woods to see where the maple syrup trees are tapped.

Things To Do Near Woodstock, VT

While there are so many great things to do right in Woodstock, VT, there are also lots of opportunities to explore the nearby areas to see even more of Vermont and New England. If you’re planning a trip to Woodstock and have some extra time, I highly suggest you look into some of these options.

8. Visit The Simon Pearce Flagship Store For A Glass-Blowing Demonstration

One of the my favorite things to do near Woodstock, VT is head over to Quechee, which is only about 10-15 minutes from Woodstock. Here, you’ll find quite a few things to do, including a visit to the flagship Simon Pearce store. Famous for its hand-blown glassware pieces, all of which are made right here at this location or their shop in Maryland, your experience here will be really fun and unique.

First, the grounds are beautiful, and the shop overlooks the river and a covered bridge, and the entire store is impeccably merchandised. On site is also an amazing restaurant with views of the river and covered bridge, and it serves both lunch and dinner.

But the best thing to do during your visit is to head downstairs and watch the artisans as they craft each piece. I honestly didn’t think I would find this interesting when I first visited, but it’s now one of my favorite things I’ve done in Vermont.

9. Hike The Quechee Gorge Trail

Also in Quechee, the Quechee Gorge Trail is something you don’t want to miss for awesome views of the gorge. My favorite time of year to do this is in the fall when the foliage surrounds the gorge, but this is really a great thing to do year-round (even in winter!).

The relaxing walk around the gorge is pretty easy, and it’s just under a 1.5 mile loop that typically takes less than hour.

10. Go Antiquing At Quechee Gorge Village

We’re not done with Quechee just yet! A 5-min drive from Simon Pearce brings you to the Quechee Gorge Village, and this is definitely one of the best things to do near Woodstock, VT. This quaint little outdoor shopping village sits in the countryside and here, you can shop for antiques, browse pieces by local artisans, and sample more cheeses, wines and fudge. This is a place I always have to stop at when I visit the area.

11. Taste Locally Made Spirits

While all the shops at the Quechee Gorge Village are worth your time, one place that stands out as an especially fun experience is the Vermont Spirits Distilling Co. Complimentary tastings are offered during your visit, and they hand-craft small batches of bourbon, vodka and gin right in Quechee.

If you happen to be in the area on a Tuesday, definitely stop by for their creative cocktail bar event, held each week year-round (be sure to confirm before making a special trip, however!).

If you have a special interest in local beer and spirits, it may be worth considering this awesome tour through Woodstock. A local guide will pick you up at your hotel in Woodstock, and take you to the best distilleries and breweries in the area, and do all the driving. This leaves you free to relax and enjoy whichever samples you’d like.

Click here to book your brewery & spirits tour in Woodstock!

12. Sample The Brews At Long Trail

Continuing on with sampling some of the best drinks to come out of Vermont, Long Trail Brewing Co. is also a nice place to stop. Not only are the beers great, but their taproom has an outdoor seating area with views of the river and green mountains.

During your visit, you can get a beer flight to sample different kinds (or just go for a glass), and they also have a really tasty food menu for both lunch and dinner.

13. Take A Day Trip To Stowe

I love Stowe equally as much as Woodstock, and if you have a few days or more during your visit, I highly suggest venturing over to Stowe for the afternoon, or a full day. On a day trip here, you can visit one of my all-time favorite general stores (the Stowe Mercantile), walk a beautiful and scenic path which is especially amazing in the fall and take a gondola ride up to the highest peak in Vermont.

14. Spend An Afternoon In Hanover, NH

When you’re in Woodstock, you’re actually pretty close to the New Hampshire border, and you can easily take a quick 30-minute drive to Hanover. Home to Dartmouth College , this is another great little New England town with a really beautiful Main Street for shopping and dining, and is also home to some lovely museums. Hanover makes for a great afternoon trip, and is definitely something to consider if you want to see more of New England.

Romantic Things To Do In Woodstock, VT

Woodstock makes for the perfect place to celebrate a special occasion like an anniversary, and if you’re planning a romantic getaway, here are a few ideas to consider.

15. Do A Wheel Workshop With Wine & Cheese At Farmhouse Pottery

I’ve already mentioned Farmhouse Pottery in the shopping section of this post, but for something fun and romantic, I can’t recommend the wine and cheese wheel workshop for two enough. My husband gifted me this experience a few years back, and we absolutely loved it. Sip on some wine, nibble on some cheese, get a tour of the facility, and then get your hands in the clay to create your own piece to take home with you!

Click here for more information on Clay Dates at Farmhouse Pottery.

16. Spend The Day Getting Pampered At The Woodstock Inn’s Spa

If you’re looking for the ultimate relaxing romantic getaway, definitely consider booking a spa day at the Woodstock Inn & Resort. The spa is open to the public, so you don’t need a hotel reservation to visit, and they also have couple’s massage options for the perfect morning or afternoon together. To extend your time at the hotel, you can also book a special lunch or dinner after your massage at one of their awesome restaurants.

17. Have A Candlelit Gourmet Meal At The Lincoln Inn

One of the best dining experiences I’ve ever had was at the Lincoln Inn, and this is definitely one of the best experiences in Woodstock, VT, especially for a romantic getaway.

With a dining reservation here, your evening will begin in their cozy tavern where you can buy a glass of champagne (or any drink you’d like) to kick start your experience (which I highly recommend doing), and then you’ll be welcomed into the dining room for your 7-course tasting menu curated by a Michelin Star chef.

Forbes has even named this restaurant one of the 10 best in the country, so you don’t have to go on my word alone. But my husband and I continue to rave about our dinner here, which was also very romantic.

Best Fall Activities In Woodstock, VT

Vermont is famous for its fall foliage, and this is the time of year many people choose to visit. While everything in this post is great for a fall trip, here are some extra suggestions for fall activities that you can incorporate into your itinerary.

18. Go Apple Picking

New England is a great place to go apple picking, and if you’re looking to pick some fresh apples to take home with you, there are a few options nearby. Here are some orchards near Woodstock, VT that offer apple picking:

• Whitman Brook Orchard (Quechee)
• Wellwood Orchards (Springfield)
• VTC Orchards (Randolph)

19. Enjoy The Fall Decorations Downtown

Woodstock does such a great job celebrating holidays and bringing the community together. One of the best things to do in Woodstock, VT in the fall is to admire all the fall decorations around town. Storefronts and houses alike will be adorned with fall wreaths, pumpkins and all kinds of harvest decor to get you in the fall spirit.

20. Go On A Foliage Tree Canopy Walk

Located in Quechee, the VINS Nature Center offers the incredible opportunity to walk through the forest treetops with their Canopy Walk. While this is also open throughout the summer season as well, fall is the best time to visit because of the beautiful foliage color.

The great thing about this experience is that everyone of all ages can enjoy it, including those with mobility issues, as it’s also ADA-accessible. While walking along the platforms high in the trees, you’ll have an easier time spotting birds and other wildlife, and enjoy 360-degree views of the countryside from their treehouse.

21. Visiting Billings Farms For Their Halloween Celebrations

While Billings Farm was already mentioned, their fall celebrations definitely deserve a separate mention. This event is especially great for those with children, as they’ll be able to enjoy story time, pumpkin bowling, live music and dancing. Spiced apple cider and cider donuts will be plentiful at the Farmhouse Cafe, and there will also be cider-pressing demonstrations and all kinds of other harvest activities to take part in.

22. Get A Vermont Maple Creemee At Woodstock Scoops

While Vermont is known for its maple syrup, cheese and Ben & Jerry’s ice cream, it’s also known for its maple creemees, and getting one of these should definitely be on your list. A maple creemee is basically maple-infused soft serve ice cream, and it’s awfully delicious, especially during this time of the year. The best place to get a maple creemee in Woodstock is at Woodstock Scoops, which can be found right in the town center.

Things To Do In Woodstock, VT In The Winter

Woodstock makes for a great winter getaway destination! If you’re planning to visit during this time of year, here are my suggestions for the best winter activities in Woodstock, VT.

23. Enjoy Woodstock’s Wassail Weekend In December

To kick off the holiday season, one of the best things to do in Woodstock, VT is plan a visit during Wassail Weekend in December. The town will transform into a picture-perfect Christmas postcard and is one of the absolute best places to visit in Vermont during Christmas.

During this weekend in particular, there will be a Christmas parade, the lighting of the town yule log, caroling and special holiday events at Billings Farm.

24. Ski & Snowboard At Saskadena Six

Previously called Suicide Six until just this year in 2022, this ski area in South Pomfret is only a 5-10 minute drive from Woodstock and is the perfect destination if you’re hoping to hit the slopes on your trip. This is also one of the oldest ski areas in North America, and is continually rated as a top ski destination in New England, especially for beginners. In fact, 30% of the trails are green trails!

Rental equipment is offered on the mountain, as well as lessons for beginners or those looking to brush up on their skills.

25. Hit The Ice

Woodstock has a few options when it comes to ice skating in the winter, so if you’re looking to get out onto the ice for a winter afternoon, this is a great place to do it. Woodstock has an indoor skating rink at Union Arena, and two outdoor rinks at Vail Field right in Woodstock, and Silver Lake in nearby Barnard.

A cool feature of Vail Field is that many people have donated ice skates over the years, which are stored right at the ice rink area. The rink is free for all to visit, and for those who doesn’t have skates, you’re welcomed to borrow a pair at no charge.

26. Take A Scenic Snowshoe Walk

The Marsh-Billings-Rockefeller National Historical Site is an amazing place to strap on some snowshoes and head out into the magical winter wonderland that is Vermont during this season. The Woodstock Inn & Resort maintains over 12 miles of winter trails for visitors to use, and this makes for a really peaceful day out in nature on a chilly, winter day.

Tip : To use the trails in the winter, guests must have a valid day pass. These can be purchased at the Nordic Center. Click here for more information .

27. Go Snow Tubing In Killington

Snow tubing at Killington is one of my personal favorite things to do in Woodstock, VT in the winter. While I also love skiing and ice skating, there’s something about tubing that makes you feel like a kid again, and the tubing park at Killington is a lot of fun.

Killington is about a 30-minute drive from Woodstock, which makes it easy to visit, and they have a really convenient tubing lift system that takes you back up the hill after your adventure down the hill.

Free Things To Do In Woodstock, VT

If you’re on a budget, fear not! While Woodstock can be a more expensive destination when it comes to hotels and restaurants, there’s actually plenty to do for those looking to save a little money. Here’s a list of the free things to do in Woodstock, VT:

• Visit the covered bridges (or take a Vermont covered bridges road trip)
• Walk through downtown
• Visit Sugarbush Farms
• Glass-blowing demonstration at Simon Pearce
• Walking around Quechee Gorge
• Marsh-Billings-Rockefeller National Historical Park
• Hiking Mount Tom
• Visit Farmhouse Pottery
• Tastings at Vermont Spirits Distilling Co.
• Road trips to nearby areas like Stowe, Hanover, NH and Burlington

Best Time To Visit Woodstock, VT

Woodstock is really a great town to visit year-round because it’s so charming, but fall and winter get my vote for best seasons to visit. The fall foliage in Woodstock is truly stunning, and the winter season makes for such a cozy getaway (even if you don’t ski or enjoy snow activities).

If you plan to explore more of the state during your visit, the best time to visit Vermont in general, I think, is the fall season to admire the foliage.

Best Places To Stay In Woodstock, VT

One thing to note is that Woodstock isn’t the cheapest town to visit in New England, and accommodations are usually higher than average. I’ve listed some places below in each budget category, but keep in mind that typical “budget” accommodations don’t really exist here without going outside of town.

Luxury : For the ultimate Woodstock stay, you’ll want to check out the Woodstock Inn & Resort , which I mentioned earlier in the post. This gorgeous inn is a bit of a splurge, but if you’re celebrating a special occasion, planning a romantic weekend away, or simply want to be in the center of town, this is the perfect place to stay.

Rooms are beautifully decorated with an updated take on traditional New England designs, and there are four restaurants, a gift shop and a spa on-site for your comfort and convenience.

Click here to check out the Woodstock Inn & Resort

Moderate : 506 On The River Inn is a really great option. Located just outside of the main town area along the Ottaquechee River, you’ll still only be a 5-minute drive into town. This inn has a cozy but modern farmhouse meets traditional New England style, and rooms range from standard to farmhouse suites with kitchens. Amenities include an on-site bistro, marshmallow roasting and resort privileges at their sister property in Killington.

Click here to check out 506 On The River

Budget(ish) : The Vesper Woodstock is a cute little little B&B that’s located right in town, and has a really fun eclectic and modern style. Rooms here tend to trend a little bit less in price, but you still get some really great amenities like a complimentary breakfast included in the rate, walkability to downtown and beautiful furnishings in the rooms (some with gas fireplaces and jacuzzi tubs).

Click here to check out The Vesper Woodstock

Budget Option Just Outside of Woodstock: The Align Inn is a standard budget motel that’s a great option for those willing to stay outside of Woodstock and save a bit of money. This hotel is clean and comfortable, and for the price, it’s a great option that’s only a 15-minute drive into downtown Woodstock. Plus, don’t forget about all the fun things to do in Quechee!

Click here to check out the Align Inn in Queche

Best Restaurants In Woodstock, VT

There is no storage of amazing restaurant options in Woodstock, and here, you’ll also find a big emphasis on farm-to-table dining, making this an awesome destination for foodies. There are so many places to choose from, but below are my favorite places (excluding The Lincoln Inn, which was already mentioned above in this post!).

Mon Vert Café: Right in town you’ll find this awesome little cafe that’s a great spot for a light breakfast or lunch, or a coffee. On their menu, you’ll find things like egg dishes/sandwiches and yogurt parfaits with granola for breakfast, and salads and sandwiches for lunch (and you guessed it, a focus on local ingredients from community farmers!). They also serve alcoholic drinks!

Worthy Kitchen : A menu packed with comfort foods, craft beers and delicious desserts. Located a short drive from downtown Woodstock, Worthy Kitchen is a casual place that focuses on the farm-to-table experience, and partners with local farmers to serve only the freshest ingredients. This is a popular place, and they do take reservations through Resy.com !

Mangalitsa : Located right in downtown Woodstock, this is another casual, comfort food place in an older, renovated house. Also with a focus on farm-to-table, you’ll find homemade pastas, small plates and local craft beers on their menu.

The Prince & Pauper: Also located in downtown Woodstock, this restaurants is a community staple and very popular. The interior is very cozy and decorated in a traditional New England style, and their menu is constantly changing to offer the freshest ingredients available. If you have any dietary restrictions, reach out to them before making your reservation to ensure they can accommodate you. Reservations are required as of 2022, and it’s worth the effort for a table!

Best Breakfast In Woodstock, VT

While Mon Vert Cafe is great for breakfast, I also really enjoy Soulfully Good Café. They have awesome waffles and frittatas here, which is the perfect way to start your day in Woodstock.

How To Get To Woodstock, VT

If you’re coming from a distance, the closest International airport to Woodstock, VT is the Burlington International Airport. The closest regional airport is the Lenanon Airport in New Hampshire. From the airport, you’ll need to drive.

If you’re traveling from nearby, you’ll drive directly to Woodstock, VT.

How Far Is Woodstock, VT From Boston?

Woodstock, VT is about 2 hours and 45 minutes from Boston, and there’s lots of opportunity to stop and visit fun places along the way.

How Far Is Woodstock, VT From New York City?

Woodstock, VT is about 4.5-5 hours from NYC, depending on traffic (during rush hour, it could be longer). The best way to get to Woodstock from NYC is to drive, as public transit isn’t convenient in this area of Vermont. This is another route that offers a lot of fun places to stop during your drive.

Is Woodstock, VT Walkable?

Woodstock’s town center is very walkable, but as with most destinations in New England, you will still need a car to explore nearby areas, and to get to some of the local sites and attractions. To walk around the village center, you’ll definitely be able to park your car while there, but you’ll need it to get anywhere else.

Does Woodstock, VT Have Uber?

As of 2022, Woodstock, VT does not have Uber or any ride share services. There are also no taxi companies, so your own car is very necessary in this area.

What Is Woodstock, VT Known For?

Woodstock is known for being one of Vermont’s most picturesque and charming towns with classic New England landscapes such as covered bridges surrounded by mountains and fall foliage. Woodstock has recently become famous for being the home of Farmhouse Pottery, which has garnered attention from Oprah, and is now sold in specialty boutiques across the country.

More Of My Vermont Travel Guides:

• Vermont In The Fall
• Vermont In The Winter
• Vermont In The Spring
• All The Best Things To Do In Vermont
• Things To Do In Stowe, VT
• Best Places To Stay In Vermont In The Fall
• What Is Vermont Known For? I’ll Tell You!
• Vermont Covered Bridge Road Trip Itinerary
• Best Vermont Pumpkin Patches & Farm Stands To Visit In The Fall
• Christmas In Vermont: All The Most Festive Things To Do
• Best Things To Do In Waterbury, VT
• Awesome Corn Mazes In Vermont

You may also enjoy:

• Best New England Winter Getaways
• Best New England Christmas Towns
• Best Day Trips In New England
• The Perfect New England Fall Road Trip
• Vermont vs. New Hampshire In The Fall

That’s A Wrap On The Best Things To Do In Woodstock, VT

Now that you know all the best things to do in Woodstock, VT, you’re ready to plan your perfect New England vacation in Vermont! Whether you’re looking for a little R&R at the Woodstock Inn’s spa, or are excited about the outdoor activities like hiking and tree canopy tours, there’s a little something for everyone that makes this one of the best towns in Vermont to visit.

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21 Best Things To Do In Woodstock, VT In The Fall (2024)

March 2, 2023

Welcome to the best things to do in Woodstock, Vermont in the fall!

Fall is arguably the most beautiful season in Woodstock, Vermont .

The small town’s rolling hillsides burst into vibrant hues of red, orange, and yellow, making it a prime destination for leaf-peepers.

But there’s more to do in Woodstock than just admire the fall foliage.

From apple picking to scenic drives and cozy fireside dinners, this charming town offers countless activities to make the most out of your autumn travels .

In this blog post, I’ll share my top picks for the best things to do in Woodstock during the fall season.

This list will help you experience all that this picturesque New England town has to offer during one of its most magical seasons.

So grab your sweater, and get ready to explore!

My posts may contain affiliate links. That means if you make a purchase through my link, I’ll receive a small commission, at no extra cost to you. Thank you for helping me continue to create free content for you!

Woodstock Essentials

Where To Stay In Woodstock

• Sleep Woodstock Motel ($)
• The Village Inn of Woodstock ($$)
• Woodstock Inn & Resort ($$$)

How To Get Around Woodstock

Make sure to reserve your rental car in advance on RentalCars.com .

1. Explore Downtown Woodstock

Exploring downtown Woodstock is a must-do activity for anyone visiting this charming New England town, especially during the fall season.

The streets are lined with quaint shops and boutiques, offering everything from handmade crafts to locally sourced produce.

One of the most popular shops in the area is Vermont Flannel, where you can find cozy flannel shirts and blankets that are perfect for chilly autumn days.

Another great spot is Clover Gift Shop, which offers a wide range of unique gifts and souvenirs that capture the essence of Woodstock.

And if you’re looking to stock up on home goods, Woody’s Mercantile has everything you need.

Book lovers should head to Yankee Bookshop, the oldest continuously operated independent bookshop in the United States.

No matter what your interests are, exploring downtown Woodstock is sure to be one of the highlights of your fall visit to Vermont.

2. Admire Middle Covered Bridge

The Middle Covered Bridge is a must-visit spot in Woodstock during the fall season!

This iconic bridge spans across the Ottauquechee River and offers breathtaking views of the surrounding foliage.

Located right across from the village green, it’s a perfect spot for taking photos, or enjoying a leisurely stroll.

Plus, it’s one of Vermont’s oldest covered bridges, so history buffs will definitely appreciate its unique design and construction.

If you visit on a sunny day, you might even catch a glimpse of the river reflecting the vibrant autumn colors.

So grab your camera , and head over to Middle Covered Bridge for an unforgettable fall experience in Woodstock.

Related: Vermont Quotes, Captions & Puns

3. Have lunch at Mon Vert Cafe

If you’re looking for a cozy and delicious dining experience in Woodstock during the fall season, Mon Vert Cafe is one of the best restaurants to check out.

Right in the heart of downtown, this charming cafe offers a warm and welcoming atmosphere, complete with rustic decor and a roaring fireplace.

It’s the perfect place to pop inside on a chilly autumn day.

And when it comes to food, Mon Vert Cafe does not disappoint.

Their menu features an array of mouth-watering dishes made with locally-sourced ingredients, including hearty soups, flavorful sandwiches, and freshly-baked pastries.

Plus, they offer a variety of hot drinks like coffee and tea that are sure to warm you up from the inside out.

Whether you’re looking for a quick bite or a leisurely lunch, Mon Vert Cafe is the perfect spot to enjoy some good food and cozy vibes this fall season.

4. Take a picture at the pumpkin fence

One of the most iconic spots in Woodstock, Vermont during the fall season is the pumpkin fence.

Located at 16 Pleasant Street, this charming fence is lined with a photogenic array of pumpkins, making for a picture-perfect autumnal scene.

Taking a photo at the pumpkin fence has become somewhat of a tradition for visitors to Woodstock during this time of year, and it’s easy to see why.

Not only does it make for a great Instagram post, but it also captures the essence of fall in New England perfectly.

So if you’re looking for one of the best photo spots in Woodstock this fall, head here.

Just make sure to be respectful, because this is a private home.

5. Visit Sugarbush Farm

If you’re looking for an authentic taste of Vermont during the fall season, a visit to Sugarbush Farm is an absolute must.

This family-owned farm has been producing award-winning cheese and maple syrup for over 75 years, and you can experience the magic firsthand.

Take a stroll through the scenic grounds, which are especially picturesque during the autumn months when the foliage is at its peak.

The short nature trails winds through the sugarbush, and past a charming chapel in the woods.

You can also take a tour of the sugarhouse and learn about the maple syrup-making process, or sample cheese in the farm store.

Make sure to take home some local maple syrup or other souvenirs from their gift shop.

You’ll even catch a glimpse of their adorable farm animals, including cows, goats, and sheep.

So if you’re looking for a fun and educational activity that celebrates all things Vermont this fall season, be sure to add Sugarbush Farm to your list.

6. Hike the Quechee Gorge Trail

If you’re an outdoor lover visiting Woodstock in the fall, hiking the Quechee Gorge Trail is a must-do activity.

Located in Quechee State Park, this scenic trail follows the rim of Vermont’s deepest gorge and offers stunning views.

The trail is relatively easy, making it accessible for hikers of all skill levels, and takes roughly 30 minutes to complete.

Along the way, you’ll have plenty of opportunities to stop and take in the breathtaking scenery or snap some photos to capture your memories.

And if you’re up for a longer hike, there are several miles of trails that extend into the surrounding woods.

So whether you’re looking for a quick nature walk or an all-day adventure , hiking the Quechee Gorge Trail is one of Woodstock’s best fall activities that shouldn’t be missed.

7. Snap a picture at Sleepy Hollow Farm

Taking a photo at Sleepy Hollow Farm is an absolute must during the fall season.

This iconic farm was once owned by famous author Washington Irving and has been featured in countless photographs, paintings, and postcards over the years.

Not to mention, it’s pretty famous on Instagram.

The farm’s picturesque red barns and rolling hills make for a stunning backdrop against the vibrant autumn foliage, creating a truly magical scene.

To really catch the best photo lighting, I recommend heading to Sleepy Hollow Farm for sunrise.

The farm itself is private property, so you can’t go inside, but the exterior offers the most gorgeous photo opportunities.

So if you’re looking for one of Woodstock’s best fall activities that’s sure to create lasting memories, be sure to add Sleepy Hollow Farm to your list.

8. Hike to the top of Mount Tom

If you love a good hike and breathtaking views, hiking to the top of Mount Tom is one of the best things to do in Woodstock, Vermont during the fall season.

The trail is located just minutes from downtown Woodstock and offers a moderate climb that takes roughly 1-2 hours to complete.

Along the way, you’ll enjoy stunning views of the surrounding foliage and can take a break at several scenic overlooks along the trail.

Once at the summit, you’ll be rewarded with panoramic views of Woodstock and the surrounding mountains that are simply awe-inspiring.

Whether you’re an experienced hiker or just looking for a fun outdoor activity, hiking to the top of Mount Tom is sure to be a highlight of your visit to Woodstock in the fall.

9. Try a Vermont Maple Creemee

No visit to Woodstock, Vermont during the fall season is complete without trying a Vermont Maple Creemee.

This delicious treat is a local favorite!

A “creemee” is basically a soft-serve ice cream that’s creamy, sweet, and delicious.

The addition of maple syrup gives it a unique flavor that’s distinctly Vermont.

One of the best spots to try a maple creemee is at Woodstock Scoops, located right in the town center.

Your taste buds will thank you!

10. Visit Billings Farm & Museum

If you’re looking for a fun and educational activity to do in Woodstock, Vermont during the fall season, look no further than Billings Farm & Museum.

This working dairy farm and museum offers the chance to learn about Vermont’s agricultural history and its modern-day farming practices.

You can explore the farm’s exhibits, watch live demonstrations, and even pet some of the farm’s resident animals, like Jersey cows and horses.

During the fall season, you can also enjoy special events like pumpkin carving, cider pressing, and other seasonal activities.

Plus, the rolling landscape makes this one of the best places to enjoy fall foliage in Woodstock.

With something for visitors of all ages to enjoy, Billings Farm & Museum is one of the best things to do in Woodstock.

11. Admire the historic homes

After you finish exploring downtown, head to Woodstock Village to admire the beautiful historic homes.

The town’s charming architecture and fall foliage create a picturesque setting that’s straight out of a postcard.

Many of the homes in Woodstock date back to the 19th century and are well-preserved, offering a glimpse into the town’s rich history.

Whether you’re an architecture enthusiast or simply looking for a leisurely way to enjoy the fall colors, admiring the historic homes in Woodstock Village is an unmissable activity.

12. Have dinner at Cloudland Farm Restaurant

Located on the working Cloudland Farm, the Cloudland Farm Restaurant serves dishes made with fresh, locally sourced ingredients.

Farm-to-table philosophy is at the heart of their culinary approach, with a focus on using seasonal produce and sustainable farming practices.

The dining experience is enhanced by the stunning views of the surrounding countryside, which provide a serene and peaceful backdrop for enjoying a meal.

Whether you’re looking for a romantic dinner for two or a gathering with friends and family, dining at Cloudland Farm is an unforgettable experience that celebrates the best of Vermont’s food culture.

13. Visit Taftsville Covered Bridge

No trip to Woodstock, Vermont is complete without a visit to the Taftsville Covered Bridge, especially during the fall season.

This iconic covered bridge spans over the Ottauquechee River and offers beautiful views of the surrounding autumn foliage.

Built in 1836, it’s one of the oldest covered bridges in Vermont and is listed on the National Register of Historic Places.

You can take a leisurely stroll across the bridge or simply admire its picturesque beauty from afar.

The area around the bridge also offers several hiking trails and picnic spots, making it a perfect fall outing.

With its charming architecture and breathtaking scenery, Taftsville Covered Bridge is truly one of the best things to do in Woodstock during the fall season.

14. Explore Marsh-Billings-Rockefeller National Historical Park

If you’re looking for a fun experience in Woodstock, Vermont during the fall season, look no further than Marsh-Billings-Rockefeller National Historical Park.

This park is not only a beautiful natural area with stunning views of the surrounding forest, but also a living museum of conservation history.

You can take guided tours of the historic mansion and gardens, which were once owned by three generations of conservationists: George Perkins Marsh, Frederick Billings, and Laurance Rockefeller.

The park also offers several hiking trails that provide access to beautiful scenic vistas and prime leaf-peeping opportunities during the autumn months.

With its rich history and natural beauty, Marsh-Billings-Rockefeller National Historical Park is truly one of the best things to do in Woodstock during the fall season for both nature lovers and history buffs alike.

15. Stay at Woodstock Inn & Resort

For a luxurious and relaxing getaway in Woodstock, Vermont during the fall season, staying at the Woodstock Inn & Resort is an absolute must.

This historic inn offers elegant accommodations with traditional New England architecture and décor, as well as modern amenities such as spa services and fine dining options.

The inn’s location in the heart of Woodstock also provides easy access to all of the area’s fall attractions.

With its cozy atmosphere and prime location, the Woodstock Inn & Resort offers something for everyone during the autumn months in Vermont.

Click here to check availability at Woodstock Inn & Resort.

16. Take a day trip to Stowe

Stowe , Vermont is a charming mountain town known for its picturesque New England scenery, stunning views, and vibrant fall foliage.

It’s one of the best day trips from Woodstock, and I highly recommend it!

You can explore the quaint downtown area, which is filled with local shops and restaurants.

Or, take a gondola ride up to the top of Mount Mansfield for panoramic views of the surrounding landscape.

Make sure to fill up on fresh apple cider and apple cider donuts at Cold Hollow Cider Mill.

Stowe also offers several hiking trails that provide access to beautiful waterfalls and other natural attractions.

With its classic Vermont charm and breathtaking autumn scenery, taking a day trip to Stowe is truly one of the best things to do near Woodstock during the fall season.

Related: 25 Best Things To Do In Stowe, Vermont In The Fall

17. Browse Woodstock Farmers Market

If you’re looking to experience the best of Vermont’s fall harvest, a visit to the Woodstock Farmers Market is a must.

This vibrant market offers an array of fresh produce, artisanal cheeses, baked goods, and other locally made products that capture the essence of autumn in New England.

You can browse the stalls and sample seasonal treats while taking in the lively atmosphere and stunning scenery of the surrounding countryside.

The market also hosts live music and other events throughout the season, making it a fun and festive destination.

Whether you’re looking to stock up on farm-fresh ingredients or simply soak up the sights and sounds of fall in Vermont, the Woodstock Farmers Market is definitely one of the best things to do in Woodstock in fall.

18. Take a Forest Canopy Walk

If you’re looking for a unique way to experience the beauty of fall in Vermont, add a canopy walk at the Vermont Institute of Natural Science (VINS) to your list.

This exciting attraction allows you to explore the treetops from a whole new perspective, with suspended bridges and platforms that offer panoramic views of the surrounding forest.

Along the way, you can learn about local wildlife and ecology from knowledgeable guides who share their passion for nature with enthusiasm and expertise.

The canopy walk is especially breathtaking during the fall season when the foliage is at its peak, adding vibrant hues of red, orange, and gold to the already stunning landscape.

It’s also ADA-accessible, making it a great activity for all ages and mobilities.

Whether you’re a nature lover or simply seeking an unforgettable adventure, taking a canopy walk at VINS is definitely one of the best things to do in Woodstock during this magical time of year.

19. Pick apples at Whitman Brook Orchard

When it comes to quintessential fall activities, few things are as beloved as apple picking.

One of the best places to pick apples in Woodstock is at Whitman Brook Orchard.

Located just a short drive from downtown Woodstock, this family-owned orchard boasts over 30 varieties of apples that are available for picking from late August through early November.

You can wander through the picturesque orchard, breathing in the crisp autumn air and admiring the stunning foliage that surrounds them.

Whether you’re looking for juicy heirloom apples for baking or tart cider apples for pressing, you’re sure to find what you’re looking for at Whitman Brook Orchard.

20. Walk the Ottauquechee River Trail

If you’re looking for an easy hike in Woodstock, the Ottauquechee River Trail is a must-do during the fall season.

This picturesque nature trail winds its way through beautiful forests and along the banks of the scenic Ottauquechee River, offering breathtaking views of colorful foliage at every turn.

Along the way, you can take in historic covered bridges and charming New England architecture while enjoying the crisp autumn air.

With so much natural beauty to explore, it’s no wonder why the Ottauquechee River Trail is one of the best things to do in Woodstock during this magical time of year.

21. Try falconry

If you’re looking for a truly unique experience in Woodstock, Vermont during the fall season, consider trying your hand at falconry.

This ancient sport involves working with trained birds of prey to hunt for game in a natural setting, and there’s no better time to try it than during the crisp autumn months.

As the leaves change colors and nature comes alive, you can take part in this age-old tradition while surrounded by stunning scenery and majestic wildlife.

Whether you’re a seasoned pro or a first-time falconer, the experienced guides at New England Falconry will ensure that you have an incredible time while learning about these fascinating creatures.

With its perfect blend of adventure and natural beauty, falconry is one of the most unique things to do in Woodstock during the fall season.

Common Questions

Is woodstock, vt worth visiting.

Yes! Whether you’re looking for an idyllic weekend getaway or a longer vacation filled with outdoor adventure and small-town New England charm, Woodstock is definitely worth a visit.

Where can I see foliage in Woodstock, VT?

The best places to see fall foliage in Woodstock, Vermont include Mount Tom, Billings Farm & Museum, Quechee Gorge, and scenic drives along Route 4 or River Road.

What is the best time of year to visit Woodstock, VT?

The best time of year to visit Woodstock, Vermont depends on your interests and what you hope to experience!

If you love outdoor activities like hiking, biking, and fishing, the summer months of June through August are ideal.

The warm weather and long days provide ample opportunities for exploring the lush natural beauty of the surrounding area.

In the fall months of September through November, you can witness the breathtaking spectacle of New England’s famous fall foliage as the leaves turn vibrant shades of red, orange, and gold.

Winter enthusiasts will enjoy the snowy wonderland that Woodstock becomes from December through February when skiing , snowshoeing, and ice skating are popular pastimes.

Finally, spring is a great time to visit for those who want to experience Vermont’s maple sugaring season or witness the town come back to life after a quiet winter.

Whenever you choose to visit Woodstock, there’s no doubt that this charming town will capture your heart!

Posted By: Arabella · In: travel

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August 29, 2023 at 6:51 pm

Wonderful information about Woodstock. Planning on visiting Columbus Day weekend. Would like to receive listing of places to stay.

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Explore Vermont

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Planning a Woodstock fall foliage getaway is a perfect choice for anyone looking to explore Vermont.

Consistently ranked as one of the best and most beautiful towns to visit , Woodstock is gorgeous and enjoyable any time of year. And when it comes to fall, this Windsor County town—home to covered bridges, cozy shops, and meandering dirt roads—offers loads of New England charm and autumn fun.

Patrick Fultz, who owns the Sleep Woodstock motel with his wife, Leslie Browne, says it’s possible to visit Woodstock several weekends in a row and not do the same thing twice.

“People ask us all the time, ‘Where should I go?’ We tell them to just slow down,” says Fultz, who is gearing up for a busy fall season. “It’s not about getting from point A to point B. There’s a whole bunch of stuff in between. Enjoy that because there’s so much beauty.”

Making the Most of a Woodstock Fall Foliage Getaway

-Sleepy Hollow Farm/Shutterstock

A Woodstock fall foliage visit can include everything from hiking and scenic drives to events, art, and culture. Here’s a round-up of places to visit in Woodstock and things to do in Vermont this fall .

Billings Farm & Museum in Woodstock

Billings Farm & Museum, a historic dairy farm, was founded in 1871. Billings Farm hosts a variety of fall events, including a Wagon Ride Weekend in September and a Harvest Celebration in October.  Visit billingsfarm.org for more information.

Stroll Along Woodstock’s Central and Elm Streets

In the heart of Woodstock are streets that are perfect for an autumn stroll. Central Street is home to the Yankee Bookshop, Vermont Eclectic Company apparel store, Unicorn gift shop , Mont Vert Cafe , and Soulfully Good Cafe . Elm Street is where you’ll find The Woodstock Gallery ,  F. H. Gillingham & Sons general store , and Woodstock History Center,  and more. Near the Village Green is The Woodstock Inn & Resort and Middle Covered Bridge.

-courtesy photo/Billings Farm

Marsh-Billings-Rockefeller National Historical Park

Vermont’s only national park is where visitors can tour a mansion and gardens, hike trails around Mount Tom, and visit the conservation stewardship exhibit at the Carriage Barn Visitor Center. Visit www.nps.gov for more information.

Fall Views on Mount Peg Overlooking Woodstock

An easy hike up Mount Peg offers panoramic views of Woodstock and the surrounding hills.  Enjoy a picnic when you reach the 1,080-foot summit and soak up the fall beauty.  Visit woodstockvt.com for more information.

Vermont Institute of Natural Science (VINS)

Visit VINS, an environmental education and avian rehabilitation organization in nearby Quechee, to see raptors, songbirds, reptiles, and more. Walk nature trails and explore the exceptional Forest Canopy Walk. Visit vinsweb.org for more information.

Simon Pearce

Along the banks of the Ottauquechee River and next to the Quechee Covered Bridge is Simon Pearce’s Flagship Store and Restaurant. The location’s glassblowing studio offers the opportunity to watch artisans create functional and beautiful works of art. Visit simonpearce.com for more information.

Scenic Fall Foliage Drives

Woodstock offers plenty of scenic roads to explore. From the center of town, take Route 106/South Road through South Woodstock, where you’ll find the South Woodstock Country Store and the Kendron Valley Inn’s Ransom Tavern .

Also try Route 12 from Woodstock to Barnard for scenic rolling hills, a country store, and a rural landscape, or follow Route 12 to Pomfret Road to Suicide Six ski area.

For more information about Woodstock, visit woodstockvt.com .

-Photo courtesy of Sleep Woodstock

Happy Vermont Podcast

Patrick Fultz and Leslie Browne wanted to buy a house in Woodstock. Instead, they end up purchasing and renovating the 12-room Sleep Woodstock motel on Route 4 in 2013.  In this episode, “Slowing Down and Finding Happiness in Woodstock,” the couple talk about why they decided to move to Vermont and what advice they give to guests who are visiting the area.

Listen to the podcast on Podbean.

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Fall Things to do in Woodstock, VT

Fall is the best time to visit Woodstock, Vermont! The leaves are changing colors, festivities are in full swing, the air is crisp, and the town looks like something out of a movie! Throw in a classic New England bed and breakfast, and you’re all set. Here’s my list of things to do in Woodstock Vermont!

It’s my favorite time of the year again – fall!

And there’s nothing like leaf-peeping in New England. The fall foliage in Stowe and Woodstock is unreal. It’s something out of a magazine. It’s something that I highly recommend for anyone who loves autumn as much as I do. Crisp yellows, burnt oranges, and if you’re lucky, a full-on fire engine red. 

Being from Texas means that we don’t get to experience a real autumn here. The leaves don’t really change colors. They’re usually bright green one day and brown the next. Pumpkins don’t show up on front porches until a week before Halloween because it’s honestly too hot and they would melt.

That’s not the only reason I love Vermont though! They have some of the highest quality fresh produce, maple syrup, and dairy, so you know everything you’re going to eat is going to be farm fresh and delicious. And all I’m really trying to say is that Woodstock is the perfect fall weekend trip to make with your beau. It’s laid back and oh, so perfect for the season. 

Here’s everything you need to do, when to go, and what to know for your fall Vermont trip!

Things to know:

It can vary quite a bit! There are plenty of websites that have predictors if you’re planning a trip. It’s most helpful to look at last year’s peak foliage dates when booking a fall foliage trip to Stowe or Woodstock, VT, and use that to plan your trip.  Here  is a website that will give you an idea of what dates were best for leaf-peeping last year. I find that anywhere between October 5th-20th tends to get you decent colors!

Seeing fall foliage is one of the best things to do in Woodstock. So naturally, everyone flocks to Vermont during this time. We booked our trip 4 months in advance, and it proved to be late. A lot of the inns and bread and breakfasts we wanted to consider were already fully booked out for our dates. So if you’re serious, I would have your trip booked 6 months in advance. This will guarantee you have a chance to snag affordable accommodations. Keep in mind that Woodstock is really small, and there aren’t too many inns around. Airbnb or VRBO might be something to consider too. You may also want to consider staying in Lebanon, NH and driving into Woodstock for the day.

Woodstock is tiny. Tiny enough to bike and see the whole place! But there are activities to do here in Woodstock and in neighboring towns. I would say you don’t need more than a 48-hour weekend to see and do everything!

Since we were flying in from Houston, Burlington was the nearest airport to Woodstock. Keep in mind – Burlington Airport is SMALL. And I mean really small. The car rental agency we used made us wait close to 2 hours even though we had a car reserved for pick up. I don’t know if it’s the labor shortage or if it’s something that’s normal because of the time of year. But this is something to keep in mind. Plan on waiting. This obviously wouldn’t be an issue if you live close and make a road trip from Boston, Albany, New York City, or somewhere else close by!

What to do during Fall in Woodstock, VT.

• Ride the Green Mountain Railroad:  located ~45 minutes outside of Woodstock, this is a great way to see all the fall foliage! Guests of the Green Mountain Railroad enjoy a 2-hour trip through Vermont’s scenic countryside during September and October. Overlook mountain, rivers, and wildlife from the windows of the rail cars. They also offer a 4-course dinner train.
• Middle Covered Bridge:  When I think of Woodstock, this is the first image that comes to mind. The quintessential perfect covered bridge. Be prepared though, there’s almost always a crowd here.
• Visit Farmhouse Pottery:  A lot of the props I purchase for the blog are from here, so I spent the better part of the afternoon in this store and couldn’t pass up the chance to add this to my list of things to do in Woodstock. I walked away with a few things, but the best part is that they offer to ship the items to your door – perfect if you’ve only brought a carry-on!
• TIP:  come early and be prepared to walk around! If you get here early, you’re more likely to get a good parking spot – without having to drive around for a while. Plan to be on foot for the rest of your stay in downtown because the spots are almost always full.
• Check out the Woodstock Inn & Resort:  During the holidays, this place is fully decked out with festive flowers and lots of pumpkins. Unfortunately, we made it the week before all the flowers were replaced with yellows and oranges. But nonetheless, this is a sight to see on your stroll.
• TIP:  A lot of the images you see online are a bit misleading as they’re taken much further down the driveway of the farm. I don’t recommend doing this unless you’ve obtained special permission to do so!
• 3429 Cloudland Rd South, Woodstock, VT 05091
• Billings Farm & Museum:  This place is on the way to the Sleepy Hollow Farm. It’s a classic creamery with tons of animals. It’s a great place to take the kids if you’ve got the little ones with you! They also have an ice cream shop on the premises.
• FH Gillingham & Sons:  Located near the main street. This is a classic Vermont General Store in Woodstock’s downtown that sells a little bit of everything! From pottery to kitchen utensils, cider, pumpkin butter, and so much more.
• TIP:  This farm is located at a higher elevation. Meaning that if it’s a particularly cloudy or foggy morning, you may want to get here later in the day. That way your pictures aren’t just a bunch of fog!
• 1279-1163, Jenne Rd, Reading, VT 05062
• Taftsville Covered Bridge:  just a place to stop for a quick picture; it’s a red covered bridge. Keep in mind there isn’t much parking here, so you’ll want to steer off the road or maybe opt to just drive under the bridge instead.
• Woodstock Farmers Market:  Don’t be fooled by the name – this is not your typical farmers market lined with vendors! This is more of a grocery store. But it’s a lot of goods from local farmers in the area and locally sourced ingredients. This place is close by to Farmhouse Pottery and has prepared snacks, hot cider, and everything else. Visitors often make a pit stop in here to grab a warm drink, a sandwich, or souvenirs!
• Sugarbush Farm:  A cute little family-owned farm with acres and acres of land. Taste Vermont cheddar, maple syrup, and so much more. The employees are all so nice here, and they even have a maple syrup museum. It gave me Stars Hollow museum vibes (if you know, you know) but it was still cute! Make sure you stop by the gift shop to pick up maple syrup. We loved the flavor of their dark amber maple syrup.
• TIP:  Even if you decide not to hike the trail, I do suggest stopping at the viewing point at the top to take a picture. The gorge looks stunning with all the fall foliage and definitely a must-do on my list of things to do in Woodstock.
• Take the scenic route to Stowe:  Depending on how much the leaves have changed color, you might want to consider taking the scenic route to Stowe (if you’re headed there.) This does add ~40 minutes to the drive time than if you were to take the highway, but depending on the time of year, it might be worth it! Otherwise, hop on the I-89N and make your way into Stowe.

Where to eat in Woodstock, VT

• 28 Central St, Woodstock, VT 05091
• 442 Woodstock Rd, Woodstock, VT 05091
• 7161 Woodstock Rd, Quechee, VT 05001

I hope this gets you in the mood for fall.

I’m ready for pumpkin spice lattes, cozy sweaters, and spooky season!

If you like this post, you may also want to check out:

• Fall in Stowe, VT
• Girls Trip to NY
• Road Trip: Seattle to LA
• A Weekend in Chicago
• Tips for Visiting the Wizarding World of Harry Potter

published on Sep 15, 2022

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Cruising through Vermont during fall foliage season has always been at the “peak” of my bucket list.  Although I live in Connecticut and enjoy gorgeous autumn colors here as well, the allure of the reds and oranges further north, and the promise of quintessential “Gilmore Girls” type towns, has always had me itching to plan a Vermont getaway.  As an added incentive, it was time for my husband and I to celebrate our 5 year anniversary — just the two of us!  Yippie!  Whether you have Woodstock on your must-visit list as an adult getaway, or instead as a family destination, you won’t be disappointed.  It’s a little town that packs a big punch of fun.  This fall guide to Woodstock includes everything you need to know about where to stay, places to eat, and nearby activities to fill your autumn weekend.

For your Planning Purposes

Getting there:  The closest airports are Boston, Manchester, Albany, and Portland.  Each airport is about 2-3 hours away.  For any New Yorkers itching to get out of town for some leaf peeping, you’re a 5 hour drive from the city, making it a great spot for a weekend getaway.

Getting around: You’ll definitely need your own car, as there are limited taxis available.  While the town itself is walkable, it will be necessary to drive to nearby hikes and sightseeing spots.

When to visit:  Woodstock is lovely to visit all year round, but high season is September-October, when fall colors are at their peak. 

What to do in Woodstock in the fall?

Highlights if you're in a hurry.

• Shop and stroll the town: Woodstock has that small “Gilmore Girls everyone-knows-each-other vibe.”  I love pocket- sized charming towns because it’s simply just impossible to go-go-go.  You’ll meander slowly through each shop, and before you know it, the whole morning will have passed!   
• Photograph Sleepy Hollow Farm:  If you’re visiting Woodstock to photograph the fall colors, then take a drive to Sleepy Hollow Farm.  It has become quite famous on Instagram, but it’s worth checking out for yourself.  
• Hike the Quechee Gorge: Hiking trails surround Woodstock and if you love the outdoors, you’ll love exploring the outskirts of town.   Quechee Gorge is a short 15 minute drive away, with an easy walking path down to the water.  Bring some snacks and enjoy the view!  

Don't Miss This Related Compass Roam Article

Interested in learning more about activities in Woodstock?  Check out this article to help plan your trip:

• How to Spend a Perfect Weekend in Woodstock, Vermont

Luxury Accomodations in Woodstock, VT

• The Woodstock Inn and Resort is the famous hotel in town!  With a memorable “mini White House” entrance, cozy lodge, and beautifully appointed rooms, it has earned its top rank as one of the best hotels in New England.  It is walkable to town, has a heated pool (open seasonally), relaxing spa, tennis courts, and 2 restaurants on site. 

Would you like to learn more about the Woodstock Inn?  Here's another article you may find helpful:

• Luxury Hotel Review: Woodstock Inn and Resort

I Also Considered This Hotel

• Jackson House Inn - This luxurious B&B is located right outside Woodstock and features some of the best breakfast spreads in town!  They offer both regular rooms and suite options, which overlook landscaped gardens.

The Best Restaurants in Woodstock, VT

Favorite spots.

• Before the town wakes up, walk over to Mon Vert Cafe for breakfast burritos, french toast, and a warm drink.  It’s one of the most popular spots in town, and by 9:30am there is a line out the door and down the street. 
• At the end of the day, stop by Worthy Kitchen for a casual dinner that serves up comfort pub fare.  I loved the black bean veggie burger and mac and cheese.
• If you prefer something a bit more fancy, the food at Simon Pearce Restaurant was delicious and elegant.  When making your reservation, request a table with views of the river.

Other Popular Restaurants

• Cloudland Farm - I most regret not booking a table here!  Cloudland farm is a working farm, with spectacular views of the rolling hills of Vermont.  The menu changes daily and is a true farm-to-table dining experience.  
• Kelly Way Gardens - If you’re visiting Woodstock in the summer months, reserve a dining experience at the off-site farm of the Woodstock Inn and Resort.  You can even arrange for guided tours and private tastings. 
• Prince and the Pauper - Located in the heart of downtown Woodstock, the Prince and Pauper is another popular option for a good date night out in the town.  
• Village Butcher - The Village Butcher is the famous deli in town, offering a wide assortment of sandwiches and meals to- go.  It’s a great spot to pick up lunch before a hike.  If you’re a vegetarian you may be happy to learn that they are famous for making a delicious veggie option called the Veggie Lover’s Delight.

Would you like to learn more about my favorite spots to eat? 

• A Foodie's Guide to Woodstock, VT 

Tips for traveling to Woodstock, VT

• Peak fall colors are tricky to plan for, and extremely weather dependent:  It’s a little bit of luck of the draw when it comes to seeing the perfect autumn scene -- sometimes the brightest Vermont foliage arrives in September, and other years the colors brighten around mid October. A drought, or conversely, an overly wet season, can throw off the foliage by a few days, or even impact the amount of leaves on the trees.  Your best bet is to plan for an end of September or early October weekend.  No matter what, if you're visiting at this time of year it will be stunning.
• Make your reservations early - especially for a fall getaway:  Woodstock is one of the most popular leaf peeping destinations in New England.  If it’s on your bucketlist, book your room now and don’t forget to make restaurant reservations as early as you can. 
• Pack for warmth:  The October mornings in Woodstock are pretty chilly!  We experienced lows in the 50’s.  Bring a warm light jacket and chunky scarf weather.  

That's a Wrap

Woodstock is a must-stop on any VT road trip itinerary, and especially so during the autumn months.  I enjoyed my weekend away and would love to return for a longer fall foliage excursion throughout more of Vermont.  It’s a beautiful state with down-to-earth people and a laid back vibe that adds to its charm and appeal.

I hope this article has inspired your fall getaway to Woodstock, Vermont.  If you have any questions, or your own travel tips, please leave them in the comments below.  Also, don't forget to sign up for the monthly newsletter, packed with travel tips, upcoming news, and access to FREE destination itineraries.

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From The Blog 11 fall activities to enjoy in Woodstock

Let the fall frolicking begin!

The Autumn season promises a bounty of foliage and family fun! So without further ado, we present to you 11 of our favorite adventures that'll immerses you in the warm, cozy feelings of the season:

1. Experience life on the farm

Woodstock offers a double-whammy of Sugarbush Maple and Cheese Farm (free samples? Yes, please!) and Billings Farm & Museum , one of the finest outdoor history museums—and a fully-functional farm, at that! Gather the whole family to say hello to friendly animals, snag an inside look at how things are made, discover hidden gems on hundreds of acres, and even partake in a round of pumpkin bowling —all under a vibrant canopy of leaves! Welcome to farm country.

Autumn... the year's last, loveliest smile

2. Pick-your-own apples on Vermont’s hillside orchards

No need to upset the applecart on your autumnal plans—because you can still enjoy this pastoral adventure in the crisp, cool air! Click here to learn about two orchards within 15 minutes of Woodstock, their policies, hours, and more.

3. Hike it out

With the recent addition of the Ottauquechee River Trail , Woodstock is more walkable than ever—offering one of the best ways to experience fall foliage! Pick your path from a quick stroll through the town green to a steep hike up Mt Tom for a panoramic view of the quaint village below—and everything in between. Click here for a list of hiking options, trail-maps, and more.

4. Catch a concert under the September sky

Pull up a lawn chair, grab a blanket, and don’t forget to attend one of these music nights! Only a few weeks remain for amazing live performances at Feast & Field in nearby Barnard.

5. Try your hand at the sport of kings

There’s nothing like watching a Harris's Hawk take flight, opening its 47” wingspan, its reddish brown feathers blending with the vibrant foliage below.

You can learn about the ancient passtime of falconry and even handle and fly a trained bird-of-prey yourself at the Historic Rutherford Barn on Woodstock’s Hartland Hill Road. Reservation only.

6. Shop local

Admiring our historic storefronts and perusing the wares of lovely mom-and-pop shops is a pastime all its own! Many of our shops are open for (in-person) business, just be sure to wear a mask both on the village sidewalks and within each business.

7. Grab the reins in horse country

Saddle up for everything equestrian, from fall foliage pleasure rides across miles-and-miles of dirt roads, wooded trails, and meadows to an autumnal dressage show with The Green Mountain Horse Association (GMHA) nestled in bucolic South Woodstock. Don’t forget your riding boots and bridles. We’re not horsing around on this one.

8. Immerse yourself in the trees at the VINS Canopy Walk

The Vermont Institute of Natural Science (VINS) in nearby Quechee is a nature lover’s wonderland, and the Canopy Walk , added in 2019, takes the nature center to new heights. Between visiting rehabilitated birds in their outdoor enclosures and learning what it takes to care for these fascinating fowl, take to the treetops via an ADA-accessible boardwalk that rises as high as 81 feet (or four giraffes) above the forest floor, affording panoramic views of autumn’s colorful display, Dewey’s Mill Pond, and beyond.

9. Take farm-to-table literally

Inside the spectacular Red Barn at Kelly Way Gardens, dine on the produce plucked fresh from the grounds, brought together with local cheeses, honey, dairy, and more via menus handcrafted by Woodstock Inn & Resort Executive Chef . But don't delay, because this reservation-only dinner series concludes in September!

10. Get creative with Artistree’s classes

You can dance if you want to—or paint, write, cook, perform, and create in endless ways because Artistree’s fall classes are in session!

TO ACCESS MORE GREAT CONTENT ON OUR BLOG...

From the blog the perfect weekend in woodstock: fall edition.

Planning a Vermont fall getaway? With our 3-day Woodstock weekend itinerary, your scheduling just got easier - as we cover the best lodging, dining, and leaf-peeping activities under the autumn sky.

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North America · October 31, 2020

How To Spend a Perfect Day in Woodstock, Vermont

Woodstock, Vermont is a small town, which was named “ the quintessential New England village” and for good reason! Walking around Woodstock kind of feels like you’ve been placed on the film set of Gilmore Girls and you’re in a beyond charming, dreamy, rural fantasy land. Woodstock, Vermont is filled with beautiful, locally-owned shops, adorable cafes and restaurants, picturesque covered bridges, and stunning, historic 19th-century buildings.

On a recent girls’ trip to Vermont, we spent a full day exploring Woodstock and its surrounding areas. Every bit of Vermont that we managed to see over that weekend was mesmerizing, but Woodstock left a lasting impression on us.

If you’re planning a trip to Vermont I assume you’ve stumbled upon this post because you’re interested in including Woodstock in your itinerary. Or maybe you’re just considering it. Well, I’m here to tell you that Woodstock should 100% be on your Vermont must-visit list! I also want to share this guide on how to spend the perfect day there. In this post, I will have you covered with wonderful restaurants to eat at, the best places to take in the views, great tips for visiting Woodstock, and I’m even including a road map of the day. So let’s get to it!

Table of Contents

For Other North America City Guides, Check Out These Blog Posts:

• The Ultimate Guide to Buffalo, New York
• A Perfectly Packed Three-Day Guide to Washington, DC
• Things To Do in Ellicottville, New York During The Summer

Getting To Woodstock, Vermont

Vermont is a relatively small state and getting around is quite easy. The largest airport in Vermont is Burlington. Chances are if you’re flying, this is the airport you’ll be landing in. Burlington is in the north and right near the border of New York State. Here, we rented a car and did a little road trip down to Woodstock, which is in central Vermont. Not including any stops that we made along the way (also just to mention our accommodation was about 30 mins outside of Woodstock in a town called Pittsfield) the drive from Burlington to Woodstock is just about 1 hour & ½.

If you’re driving, I’m sure there will be a point in time where you find yourself on Vermont Route 100. This is Vermont’s most scenic drive! It runs through the center of the state, north to south, and there are plenty of picturesque places to stop along the way.

While on your way to Woodstock, keep a lookout for spots on the road that you can stop off. The drive has many twists and turns so areas to stop off come up very quickly. But, if you happen to see an extra-large shoulder on the road, it’s totally worth it to pullover (ONLY WHEN IT’S EXTREMELY SAFE TO DO SO) and really take in the scenery. 

How to Start off Your Day

First things first, any day in a new town or city should start off with a fantastic meal! Woodstock is filled with tons of cute cafes offering up great breakfast and brunch menus. Take a stroll down Central Street and consider having your first meal at one of these amazing places:

Mon Vert Cafe

Mon Vert was our very first stop once we arrived in Woodstock. We realized that everyone in town had the same idea as us when we noticed the line down the block. Mon Vert is an extremely popular cafe serving up breakfast & lunch dishes prepared with organic, local ingredients. They are also very passionate about their coffee! Unfortunately, we were a little too hungry to wait for the line to die down so we moved on. However, if you manage to reach Woodstock on the earlier side and can get in before the crowd, I’ve heard that Mon Vert does not disappoint. They are open Friday- Wednesday 9 am- 4 pm and you can access their menu here .

Soulfully Good Cafe

Since we struck out with plan #1 we moved onto #2, which was just a short walk down the road. Soulfully Good Cafe is a very cozy, welcoming place with a cute outdoor patio as well as indoor seating. They serve breakfast every day until 11:30 am and then they move onto their lunch menu which is served until 3 pm or 4 pm, depending on the day. We unfortunately just missed the cut off for breakfast but were happy with their simple, yet delicious lunch menu filled with salads & paninis. We were still in a brunch mindset though so we added on a couple of rounds of mimosas too! Initially, we were a bit disappointed that we didn’t get to eat at Mon Vert, but we couldn’t have been happier with Soulfully Good! Check out their menu here .

Where to Spend Your Afternoon in Woodstock

After you’ve gotten in your first meal of the day it’s time to do some exploring! Continue your stroll down Central Street. There are plenty of adorable shops worth stopping in and depending on what time of the year you visit, the storefronts are all festively decorated and very cute!

The best time of year to visit Woodstock is during the fall months, specifically when the foliage is at its peak. This varies year to year but generally, you’re looking at the end of September to mid-October. During this time the town is all dressed up with pumpkins and festive autumn decor. You also just cannot beat the natural beauty that Woodstock offers during this season! There are many destinations out there that I would recommend visiting during the offseason, but Woodstock is not one of them.

While wandering around town, there are a couple of specific places I would recommend checking out:

Woodstock Middle Bridge

Vermont is quite well-known for all of its covered bridges- to be more precise, there are over 100 of them! Some of them date back to the 1820s but most were constructed from the mid to late 19th century. Just off of Central Street you will stumble upon Woodstock Middle Bridge. This is a beautiful, wooden covered bridge that will have you imagining that you’ve laid your eyes on a painting. A great feature of Middle Bridge is that there is also a path for pedestrians wanting to walk over and the views are stunning! This area can get a little congested between tourists (like myself) wanting to take photos and cars wanting to actually use the bridge for its intended purpose, but with a little patience, it was easy to have the place pretty much to ourselves.

Teagle’s Landing/ Kedron Brook

While walking down Central Street you will discover a set of wooden stairs that leads down to a river. This is Kedrom Brook. You’ll know you’re in the right place when you see the sign “Teagle’s Landing”. This small oasis is named in honor of Frank H. Teagle, Jr. who was a Woodstock resident from 1945 to 1997. He was a thoughtful and selfless man who worked to make his community a better place. This lovely area has been dedicated to him. It’s such a beautiful little piece of nature running right under a buzzing street. Take a walk down here to enjoy it for yourself.

Check out These Super Cute Shops

As I’ve mentioned before, Woodstock is filled with tons of cute shops! And if you’re strolling down Central Street you’ll have no choice but to walk passed them so you might as well stop inside. I would definitely recommend checking out Yankee Bookshop. This is Vermont’s longest-running independent bookstore, which opened in 1935! They have books, vinyl, stationery, and gifts. Then there’s F.H. Gillingham & Sons which has tons of great quality local products such as maple syrup, cheese, macaroons, honey, and so much more. Lastly, Red Wagon Toy Co. is an adorable shop and a great place to buy gifts for any little ones in your life. A friend that was on this trip with me just had a baby six months ago and this place was perfect for finding something to bring back home to her.

Exploring The Surrounding Areas of Woodstock, Vermont

After taking the time to walk around town and enjoy the literal charm in the air that Woodstock gives off, it’s time to explore out a little bit further. All of these stops are within a 15-minute radius of Woodstock and I would highly recommend all of them!

Billings Farm & Museum

Billings Farm is not just a working farm, but it’s also an extensive museum dedicated to scientific farming history. Located just a short 2-minute drive outside of town, you’ll experience the beautiful Vermont countryside here at Billings Farm. Through their tours, they offer diverse, interactive programs that focus on rural life, traditions, and values dating back to the 19th century. If you’re interested in discovering more about Vermont’s rural history, this is a great place to start. If you’re not interested in taking a tour Billings Farm is still a beautiful place to see Vermont’s scenery, enjoy the autumn foliage and even spot a couple of cows.

A 17-minute drive from Billings Farm will bring you to Jenne Farm, which is not only the most photographed farm in Vermont but in all of North America. Let me just tell you right now, it is beyond gorgeous! You’ll enter a dirt road that is technically two-way but you’ll wonder how two cars are meant to drive down it at the same time. I’d recommend parking a little ways from the farm and walking the rest of the way to take in the scenery. The rolling hills, beautiful valleys of green, and outstanding colors of the changing leaves will leave you absolutely breathless!

Jenne Farm is a private residence so always be respectful when walking around and taking photos of the property. It obviously doesn’t cost anything to visit Jenne Farm, but there is a donation box on the premises.

Quechee Gorge

About 15 minutes east of Woodstock is Quechee Gorge. This one we stumbled upon by mistake and it ended up being one of my favorite parts of the trip. We were seeking out a winery and my google maps led us to Quechee Gorge Village- a connection of different antique and souvenir shops, homemade fudge, a grocer with local products, and a little corner where wine is sold. (Not exactly the winery we had in mind) On the left-hand side of Quechee Gorge Village is an adorable Alpaca Farm and just over the bridge is “the” Quechee Gorge, a sight absolutely worth seeing! It’s one of those views that are completely untouched by mankind and have seemed to remain just as mother nature intended it to. What do you think?

Finishing off Your Day

After a full day of taking in the sights and exploring a beautiful, new place, it’s time to end the day with another delicious meal. Woodstock isn’t short of amazing places to eat and I’m going to share some wonderful recommendations with you:

If you can, make dinner reservations! I’m assuming it’s because we visited during the peak time of the year but every restaurant we walked into had anywhere from 30 minutes to over an hour wait. We even went to dinner on the earlier side (before 5 pm) thinking it would make a difference but it did not! Make reservations and avoid the hassle. 

Cloudland Farm

Dining at Cloudland Farm was our first choice and I really dropped the ball on this one. I should have called for reservations weeks in advance and it was one of those things that just slipped my mind. Of course, the evening that we wanted to have dinner there, they were completely booked out. However, if you plan ahead a little bit better than I did, having dinner at Cloudland sounds like the way to go. They offer up a true farm-to-table dining experience with a rotating tasting menu and beautiful countryside views. Check out their website here .

Worthy Kitchen

Worthy Kitchen is just a short drive outside of town and is a very popular spot amongst locals and visitors alike. They are all about craft beer, delicious, local food, and most importantly, creating a community. Check out their menu here .

Dr. Coburn’s Tonic

Dr. Coburn’s is a cute spot right in town and this is where we actually ended up. They don’t have a super extensive menu, but there’s a little something for everyone. Their cocktail list was great and had some delicious seasonal options. We started off with the chicken wings which were very good and if you’re a fan of wings I would definitely recommend trying them in Vermont. Most places offer a really tasty maple syrup-hot sauce blend, which is an incredible mix of sweet and spicy. This is a perfect restaurant to eat at if you’re finishing off your evening right in town and want to go somewhere walkable and cozy. Check out their website here .

I Hope Woodstock, Vermont is as Good to You as it Was to Me!

As I conclude my perfect day in Woodstock, Vermont guide, I would also like to share with you the road map of our day in case you would like to follow along a similar route! Please see the screenshot just below. I hope this guide has given you some inspiration and ideas for planning your own trip to Woodstock and if and when you make it to this incredible town, I wish you the very best time. Please feel free to leave any questions or comments below and as always, happy travels!

You’ll Also Love

November 2, 2020 at 4:28 am

Loved all your fabulous fall pictures and your informative travel tips…thanks for sharing! Love, Aunt Lee XOXO

November 3, 2020 at 6:55 pm

Thank you, Aunt Lee! So happy you enjoyed them 🙂

January 16, 2021 at 11:55 pm

I love the efforts you have put in this, thanks for all the great articles. Sharron Stefan Heaps

[…] For a full guide on how to spend a perfect day in Woodstock check on my blog post here. […]

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Four Fun Places to Experience Fall in Western New York

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15 Best Things To Do In Woodstock, Vermont

by Mark and Kristen Morgan

Published: August 9, 2021

The tiny town of Woodstock in central Vermont epitomizes a captivating and quintessential New England village, filled with attractive historic buildings and a relaxing aura. So what should you do when you visit such a tranquil place? Well, we’re going to show you the 15 best things to do in Woodstock, Vermont to get your travel itinerary filled up to the brim.

Woodstock may be tiny in size but it is enormous in popularity and it is one of the most visited places in all of New England during Fall . Visiting Woodstock falls into the category of ‘a calming and peaceful escape’, which might come as a relief if you are driving a longer and more action packed New England road trip.

There are a a handful of must-visit attractions in Woodstock but there is no need to rush around. Woodstock is one of the most beautiful places to visit in Vermont . It is a place you take things slowly, enjoy the finer things in life and appreciate the sound of birds chirping or colorful leaves rustling in the wind.

Descriptive words like quaint, charming and picturesque can be overused at times. However, in this instance, the extraordinarily idyllic town of Woodstock in central Vermont is all of those adjectives, with a splash of enchantment and a dash of irresistible appeal thrown in for good measure.

Let’s take a look at 15 of the best things to do in Woodstock, Vermont!

Top Tips For Visiting Woodstock In Vermont

Before we jump into the best things to do in Woodstock VT, let’s take a brief look at some our top tips for you to consider when planning your trip:

• Woodstock is an incredibly popular touristy stop off in Vermont.
• We highly recommend including a stop in Woodstock on any USA road trips including Vermont.
• It’s hard to put into words how beautiful Woodstock is in the Fall season.
• Hotels are not cheap, so we recommend you book ahead to find value.
• If Woodstock is too expensive, consider staying somewhere nearby instead.
• Depending on your travel style, you could spend 1 hour or 1 day in Woodstock, VT.
• The town is very small but there are plenty of places to park.
• Take time to simply walk around the town and green spaces.
• But also jump in the car and drive around the maze-like narrow country roads.
• Bring spare batteries for your camera, you’re going to need them!

We enjoyed our visit to Woodstock in Fall so much that we were left with no choice but to include it in our popular guide to the 50 best places to visit in the USA .

Best Things To Do In Woodstock, Vermont

1. Admire Jenne Road Farm

The town of Woodstock is lovely to walk around, but the best way to really see this stunning part of Vermont is to explore the country roads and find magazine front cover scenes such as the one at Jenne Road Farm.

Magazine front cover is not an exaggeration. Jenne Road Farm is regarded as one of the most photographed barns in the world.

It has appeared on television adverts, every single New England fall foliage calendar and it was even used in a scene from timeless classic movie Forrest Gump.

What we love most about this experience is how understated it is. The only sign you will find is a tiny board stating ‘maple syrup’ with an arrow. There are no bells and whistles, despite its obvious fame.

We were shocked to be the only car on the dirt road when we visited in October, which is when it is most popular. It goes without saying, but keep your distance and don’t get too close to the private barn.

Photographers will typically stand in a line next to a tree close to where we took our photo above. There’s even a sign showing photographers where to stand to get this iconic New England picture.

To reach Jenne Farm, head South from Woodstock on VT-106 until you reach Jenne Road. It’s just over 8 miles and should take no longer than 15 minutes.

This is one of those truly unmissable things to do in Woodstock for serious photographers.

2. Taste Local Cheese & Syrup At Sugarbush Farm

Sugarbush Farm is a completely different experience. You won’t need your camera for this one but you will need your taste buds ready to sample 15 kinds of cheese and 4 grades of maple syrup produced on site.

Not only can you can taste delicious cheeses and syrup but you can also walk around a maple syrup self guided tour with information about tapping sap lines and boiling houses. Plus, farm animals roam the grounds in Summer, perfect for the younger kids.

The farm is open every day from 9am – 5pm and the entire visitation is free of charge. However, your wallet will be in danger once you’ve tried the cheese and syrup, you can trust us on that one!

Find more information at the Sugarbush Farm website .

3. Photograph Stunning Sleepy Hollow Farm

Finishing off our favorite farms in the area with another of those insanely photogenic Vermont postcard scenes. We have to be honest, we’re not sure why this one at Sleepy Hollow Farm isn’t quite as famous as Jenne Road?!

Remember we said we were the only car at Jenne Road? The same can’t be said here. We were two among maybe 15-18 other photographers at a frustratingly dull sunrise.

We decided to come back later in the morning once the grey blanket had burnt off and fortunately the beautiful fall colors were illuminating upon our return.

If we could choose just one place to photograph again in New England during Fall it would be Sleepy Hollow Farm. It looks gorgeous in photos but it looks even better in person.

Please remember this is a private farm and you can’t go down the road at all. There is a sign but some people choose selective reading ability at times!

Photographers – Don’t forget your tripod if you visit for sunrise, you’ll need it for low light to keep your ISO down.

Sleepy Hollow Farm is under 3 miles from Woodstock. Heading north on Old River Road, turn left onto Cloudland Road and follow it until you reach the farm. There are no parking spaces and it is on a very narrow road, so you’ll have to get your vehicle tucked right in against the side.

4. Don’t Miss Nearby Taftsville Covered Bridge

Vermont is home to more covered bridges per square mile than any other US state and Woodstock is one of the best places to set up base for a bridge hunt.

Taftsville covered bridge was built in 1836 and is the oldest standing example of a historic covered bridge in Vermont, which makes it a dead-cert on your Woodstock itinerary. It is 189 ft long and has an attractive classic red colored exterior.

A small dam and waterfall along the Ottauquechee River are located just to the northwest side of Taftsville covered bridge as you look at a map.

You can park up on Old River Road and walk down a riverside path to open up incredibly photogenic views looking back at the bridge and waterfall.

The only issue is with electrical pylons and lines, which do go some way to ruining the picture – but people need power, right?! Hopefully in future those lines can be moved underground.

5. Walk Across Woodstock Middle Covered Bridge

Taftsville is important because it’s the oldest in Vermont, but you don’t even need to leave Woodstock to see your first example of a stunning covered bridge.

In fact, the gorgeous dark wooden colored Woodstock Middle covered bridge is smack-dab in the center of Woodstock, right on the edge of ‘The Green’.

If you look on google maps, the bridge appears on Elm Street, but that isn’t correct. Woodstock Middle covered bridge is on Mountain Ave, crossing the Ottauquechee River.

There are ample places you can park alongside The Green if you’re not staying in Woodstock or are just driving through. Don’t miss the chance to walk through the bridge to grain an appreciation for expert craftsmanship and intricate details in the design.

Personally, we thought Woodstock Middle covered bridge was one of the most visually appealing of all the bridges we saw in Vermont. Not all bridges have pedestrian access, which makes this particular bridge in town one of the things you can’t miss when in Woodstock, VT.

6. See Jersey Dairy Cows At Billings Farm & Museum

One of the most popular things to do in Woodstock is to walk around the Billings dairy farm and learn about farming in Vermont from the late 1800’s to the present day.

Billings farm was established way back in 1871 and is best known for its Jersey dairy cow breeding. However, this is more than just a farm.

Not only can the kids pet farm animals and explore a working farm, there is also a huge emphasis on farming education. Exhibits and display showcase what life was, and is, like as a farmer in Vermont.

You can walk around the old farm manager’s house built in 1890, stroll along a riverside path or through gardens when in season, soak up gorgeous views over acres of land and self guide your way through farm life exhibits.

There are two dedicated parking lots for Billings farm and you do not need advanced reservations. You can either drive or walk to the farm from downtown Woodstock, which is just half a mile away.

Entrance prices are US$ 16 / adult, US$ 8 / ages 4-15 and Free for under 4’s.

Opening hours vary depending on season, check times here .

7. Explore Quechee Gorge and Village

Quechee is a popular stop along the typical Vermont or New England road trip, but many only visit the Quechee Gorge bridge before moving on to Woodstock.

We highly recommend you set aside a little more time, firstly to walk along the easy gorge-side trail but mostly to visit the village of Quechee itself afterwards.

Views over Quechee gorge are best from the bridge, but the gorge-side walk is still picturesque and worth 15 or 20 minutes to blow off the cobwebs.

Once done with the gorge, continue towards Woodstock but turn right on Waterman Hill Road and descend until just before Quechee covered bridge.

Park up and walk through the pedestrian walkway on Quechee covered bridge. To the right you will see a collection of boulders in the Ottauquechee River, but the view to the left is the reason for including Quechee village on your trip to Woodstock.

The waterfall and dam with perfectly reflective water surface above create a stunning scene, no matter the season you visit.

See the overhanging veranda and red brick building in the photo above? That is the award winning and very highly regarded restaurant the Mill at Simon Pearce, along with a glassblowing studio, which is open to the public.

See information about glassblowing viewing hours and the Mill to book reservations .

8. Enjoy The Stunning Woodstock, VT Architecture

Perhaps surprisingly for this region in Vermont and New England, Woodstock is not quite as colonial as you might imagine.

In fact, you will find a wonderfully diverse array of 18th and 19th century architectural styles just from exploring the immediate local area.

From pristine Georgian symmetry to palladian style windows of the Federal architectural style and of course colonial revival, which is is encapsulated by the Marsh Billings Rockefeller house in the park.

All you need to do is walk around The Green, Elm Street and Central Street for an architectural feast.

The entirety of Woodstock Village Historic District is listed on the National Register of Historic Places, which says enough in itself. You just know this is going to be a remarkably charming town.

Don’t miss the Norman Williams Public Library, a beautiful building open to the public just off The Green.

9. Walk Around Woodstock Town Shops

Shopping might be the last thing on your mind when visiting a quaint town such as Woodstock, Vermont. However, shopping here is a much more relaxing experience than a typical day at the mall.

Small independent stores, bookshops, galleries, farmers markets and quaint cafes are perfectly arranged along two very pedestrian friendly streets in town.

The best part? You won’t find a tacky gimmicky gift shop in sight.

Supporting local businesses is paramount to the continued prosperity in a touristy town like Woodstock. Don’t be shy about popping in for a coffee at Mon Vert or Soulfully Good.

The one place you should definitely check out is F.H. Gillingham and Sons. We were instantly drawn to the general store simply from its exterior, but inside we found an incredibly wide range of products in a traditional and historic setting.

This family run business is still to this day run by the 5th generation since opening in 1886. It’s next to impossible to walk around and not buy something!

10. Be Wowed By Radiant Fall Foliage

As you can clearly see from our photos in this guide to the best things to do in Woodstock Vermont, we visited in Autumn for the fall foliage season.

You can visit any time of year and you will still get the same experience of a picturesque and charming town. But the colors in fall just elevate its staggering beauty to another level.

Our best advice when visiting Woodstock in fall is to explore every nook and cranny of the entire region. Let’s say within a 10 mile radius of the town.

You will find classic and iconic fall images, but you will also find unique takes on Woodstock in the Autumn by exploring off the beaten path. Visit all of the even smaller villages nearby, walk along rivers and find elevated positions to look back on the town.

With that said, if you’re not up for a drive, the town of Woodstock itself has more than enough trees to enjoy those fiery autumnal colors of the fall season.

You also can’t miss Manchester VT in the south of the state if you’re looking for more special fall colors. Manchester is located in the heart of Green Mountain National Forest, which means rolling hills of vibrant Autumnal foliage for miles.

Need a hand planning your New England fall road trip? Our popular 40+ page New England Fall Road Trip Guidebook includes the 10 best places to visit (including Woodstock VT) and 8 example itineraries ranging from 5-14 days to help you plan a successful leaf-peeping vacation.

11. Woodstock Vermont Photography Locations

This will not surprise you – When we visited Woodstock in October, every single person we saw had a camera. Even if you just use your smartphone, we can guarantee you will leave Woodstock with hundreds of gorgeous images.

So, where should you go with your camera to take home the best photos?

Well, you should start with the two farms we talked about earlier, Jenne Road Farm and Sleepy Hollow Farm are not to be missed. Next, the town of Woodstock is extremely photogenic so get busy with your camera in town.

After that, you have all of the covered bridges near Woodstock to check out. They include Woodstock Middle, Quechee, Lincoln, Tafstville and even Cornish-Windor.

There’s a lookout point near Mount Tom with exceptional views over the town of Woodstock, which in Fall are just so impressive.

But our advice is the same as before, jump in the car and drive around the narrow country roads. Try to find something new, maybe a road with colorful trees arching overhead or another covered bridge not listed on every single article online.

Don’t forget you can use your drone around rural parts of Vermont as long as not within 5 miles of an airport. This works great in Fall.

We stumbled across possibly the most stunning covered bridge when driving to Jenne Road Farm. It was just off the road leading into a private property but we hadn’t read about it beforehand.

You can see this bridge in our favorite 7 covered bridges to see in Vermont .

What beautiful but unique photograph will you find around Woodstock?

12. Best Hikes Near Woodstock, Vermont

Most visitors to Woodstock will pass through in a day or maybe two, which makes finding time for a hike difficult. Especially when there are plenty of awesome hikes in other parts of Vermont, such as the awesome town of Stowe in the North.

However, for those who do have the time available for a hike on a longer visit, you have a handful of great hiking options right near town.

Don’t forget about Quechee gorge as mentioned above and remember, Woodstock is very close to the Appalachian Trail.

Mount Tom and The Pogue – The most popular hike in Woodstock is within Marsh Billings Rockefeller National Historic Park. You can access Mount Tom via multiple entrances and trailheads but we would suggest starting at the parking lot for Billings Farm and Museum. The full loop including both The Pogue (pond) and Mt Tom (Woodstock town views) is just over 4 miles with 650 ft elevation gain.

Mount Peg – This short 1.3 mile roundtrip loop gains around 300 ft in elevation to provide views looking back over Woodstock, but this time from the South side of town.

Luce’s Lookout – Set your google maps for ‘The Lookout Trailhead’ and drive a quick 8 miles north up VT-12 before turning onto Greengate Road. This is a 2.5 out and back trail with old lookout at the top providing more excellent valley views.

Woodstock Aqueduct Trails – This time set your google maps for ‘Aqueduct Trails’ and a 2.7 mile drive through West Woodstock will bring you to the trailhead. You can choose how far to hike through forest with boardwalks. Be aware that this is primarily a mountain bike trail.

13. Dartmouth College and King Arthur Flour

Have you ever looked around the campus of an Ivy League university? Why not take the opportunity when visiting Woodstock and just 20 miles from Dartmouth College?

Dartmouth is actually just inside the New Hampshire border in Hanover on the other side of the Connecticut River. The Ivy League college is the ninth oldest US institution of education, welcoming students since as far back as 1769.

Conveniently, the King Arthur Baking Company sits right on the other side of the bridge connecting the two states. Have you ever baked with King Arthur flour? It makes magic happen in the kitchen!

But what can you do a the King Arthur flagship campus?

Well, you can take a class in the baking school, watch expert bakers making bread and pastries, eat breakfast or lunch, shop for an array of baking recipes and of course accept every free sample.

See more information about visiting King Arthur Baking Company .

14. Marsh Billings Rockefeller National Historic Park

We have referenced this park a few times throughout this list of the best things to do in Woodstock, Vermont but now it’s time to get into more detail about the Marsh Billings Rockefeller National Historic Park.

Run by the NPS (national park service), this 643 acre plot of land is named after all of the previous owners of an old dairy farm and forest.

The land was transferred by the Rockefellers to the NPS in 1992 and in doing so gave Vermont its only unit within the US national park system.

You already know about the loop hike beginning and ending at the Billings Farm lot, via The Pogue and Mt Tom, but there are many more things to do once inside the park.

You can take a guided tour of the magnificent Marsh Billings House, walk under 400 year old trees on pristine Vermont carriage roads, bird watch, take a woodland workshop or cross country ski during Winter.

Be sure to check the park calendar for any upcoming events for your dates of visiting Woodstock.

Find more information including maps of Marsh Billings Rockefeller Park here .

15. Stay At The Impressive Woodstock Inn

The Woodstock Inn is the place to stay in town if you’re celebrating something special or have one final splurge in your New England road trip travel budget.

From both the outside and inside, the Woodstock Inn oozes class. It is perfectly located right in the center of The Green in town, ideal for walking to everything you might need throughout your stay.

>> Book Woodstock Inn : Direct | Booking.com

The Woodstock Inn isn’t cheap, but there are plenty of other lodging options to stay at during your time in Woodstock.

You can either read our complete guide to the 7 best hotels in Woodstock VT on our sister site Best Hotels Anywhere, or click on any of the top rated hotels in town below to see availability for your dates:

• The Village Inn of Woodstock
• Sleep Woodstock Motel
• 506 on the River Inn Woodstock
• The Woodstocker B&B
• Woodbridge Inn B&B
• Jackson House Inn

Map Of Best Things To Do In Woodstock Vermont

• Red Markers – Locations of the best things to do in Woodstock Vermont.

Click or touch the map to activate.

Zoom in and out, move around the map of Woodstock VT to find locations of the best things to see and do in the area.

More From Vermont

• 15 Best Things To Do In Stowe, Vermont
• 15 Things You Can’t Miss In Manchester, VT
• 10 Best Things To Do In Burlington VT
• 7 Stunning Covered Bridges To See In Vermont

Discover the 10 best places to visit on a New England Fall Foliage Road Trip with itineraries covering 5 days, 7 days and 10 days.

More From New England

• 17 Amazing Things To Do In Acadia National Park
• 13 Best Stops Along Kancamagus Highway Road Trip NH
• Flume Gorge NH Waterfalls And Covered Bridges Hike

We hope this guide to the best things to do in Woodstock, Vermont helps you plan your visit!

Have you been to Woodstock? What were your favorite things to do in the area?

Please let us know if you have any questions or need any help planning your visit in the comments below.

Happy Travels ,

Mark and Kristen

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Note : This article contains affiliate links. When you make a purchase using one of these affiliate links, we may earn a small commission at no extra cost to you.

All Rights Reserved © Where Are Those Morgans, LLC. Republishing this article and/or any of its contents (text, photography, maps, graphics, etc.) in whole or in part is strictly prohibited.

Mark and Kristen Morgan are travel, hiking and photography experts. Over the last 6 years traveling full time, they have explored more than 40 countries and 30 US states.

Where Are Those Morgans has been featured in USA Today, Gestalten, Get Your Guide, CityPASS and Condé Nast Traveler along with various other publications. Read more about us .

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26 Fun Things to Do in Woodstock VT: Vermont’s Cutest Town (2023)

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Woodstock is one of my favorite towns in Vermont. There is no place in Vermont that better captures the charm and beauty of small town New England than Woodstock.

I’ve spent lots of time in Woodstock during the 15+ years I lived in Vermont, and I’ve gotten to know it well—and really fallen in love with it! Woodstock NEEDS to be on your Vermont bucket list .

In this travel guide, I’m going to share with you 26 of the best things to do in Woodstock, Vermont, including the top attractions, hikes, places to eat, and the best activities for fall, winter, spring, and summer.

Let’s explore!

From sampling Vermont’s famous cheeses to hiking to strolling the historic Woodstock downtown, you’ll find a plethora of activities to keep you and your loved one busy on your Vermont vacation.

Table of Contents

The Best Things to Do in Woodstock VT

1. visit a working dairy farm – billings farm and museum.

Billings Farm and Museum is a beautiful property where you can stay busy for hours.

If you’re searching for things to do in Woodstock VT with kids, Billings Farm and Museum should top the list! This is a working farm that is all about demonstrations and education, and is beautiful, to boot!

Spending an afternoon here can show you a great deal about the inner workings of a Vermont farm, and you can see the animals up close and personal. 

I recommend checking their schedule before your visit. There are various programs and demonstrations throughout the day that may catch your interest, so you’ll want to plan around those.

2. Stroll America’s Sweetest Downtown

Downtown Woodstock, VT is a fabulous place for shopping, dining, and more. This cute area can get crowded on weekends or during busy events, and it’s no wonder–there’s lots to see and do.

This 1886 general store is a Woodstock staple, and is renowned as one of VT’s oldest family-run general stores. Stop here for all kinds of Vermont-made items, souvenirs, and a nice selection of wine.

Other shops in Woodstock VT to keep an eye out for: 

• Unicorn – unique gifts and novelties
• Yankee Bookshop – Vermont’s oldest running independent bookstore
• Vermont Flannel Company – stay cozy!
• 37Central Clothiers
• Red Wagon Toy Co.

Even if you’re not shopping, I recommend just taking a walk around in downtown Woodstock.You can explore the covered bridge, admire the iconic Woodstock Inn and Resort, or simply sit with coffee and people watch.

You never know who you might meet. On one of our trips to Woodstock, we got to meet this tiny polar bear named Oso.

3. Seek out the covered bridges

There are dozens of charming, historic covered bridges in Vermont , and the Woodstock area is home to several. 

Middle Covered Bridge is perhaps the most photographed, as it sits right in the center of downtown Woodstock, just off the Village Green.

Surprisingly, this covered bridge is on the newer side, having been built in the 1970’s. Despite that, it looks just as historic as the many other bridges in the area.

Head down Route 4 for a few miles and you’ll find the Taftsville Covered Bridge. This long red bridge, built in 1836, is an impressive 189 ft long. You can photograph it from a pull-off just down from the bridge. 

4. Admire Quechee Gorge

Woodstock and Quechee are neighboring towns in west-central Vermont, and a trip to one can’t really be complete without a trip to the other.

When you’re searching for things to do near Woodstock, VT, also look for things to do in Quechee, VT. There are so many, and Quechee to Woodstock is a less than 15 minute drive!

One of my very favorite sites in the region is Quechee Gorge. This awe-inspiring natural formation is best seen from the bridge on Route 4. There is a parking area just beyond the Quechee Gorge bridge, and the bridge has a sidewalk with rails, so you can safely walk out and peer into the gorge.

The gorge is especially magical in the autumn, when the trees on either side burst into remarkable hues of orange and red.

If you’re feeling adventurous, you can take a fairly short hike down alongside the gorge. The trail leaves from the parking area and takes you to some short waterfalls.

5. Eat Cheese, Cheese, and More Cheese at Sugarbush Farm & Quechee Gorge Village

No Vermont vacation is complete without cheese.

In the past, it was said that Vermont had a larger population of cows than people! Not hard to imagine, with farmland stretching for miles across the state. Either way, those cows are producing some great dairy, and Vermont’s cheesemakers are turning it into the finest cheese.

Cabot is the state’s most famous cheese purveyor, available in stores throughout the US. You can’t go wrong with a nice block of Cabot sharp cheddar. But when in Vermont, you want to try ALL THE CHEESES .

You can have a wonderful cheese feast at Quechee Gorge Village. As you walk through the village’s cute shops, you’ll find a huge spread of cheese samples, along with crackers and jams.

Give all the varieties a taste and buy a block to take home. With the abundance of cheese to sample, you may find it hard not to get greedy!

Cabot is not the only cheese in Vermont, not by a mile. A visit to Woodstock, VT demands a visit to a local farm.

Head up to Sugarbush Farm , a Vermont sugar house and 3 generation family farm tucked away in the hills, for more cheese sampling as well as maple syrup tasting.

While you’re there getting your fill of farm-made cheese, you can also walk around the 500 acre property, visit with the goats and horses, and learn about how maple syrup is made. 

6. Stroll the Village Green & Woodstock Village

Many of the shops downtown and other notable buildings comprise the Woodstock Village Historic District. This was listed on the National Register of Historic Places back in 1973. It includes 95 buildings and sites across the village center and along the Ottauquechee. 

The oval-shaped Village Green sits within Woodstock Village. On one side you’ll spot the covered bridge and on the other, the Woodstock Inn and The Norman Williams Public Library.

North of town are sites such as the Billings Farm and Museum, and parts of the f Marsh-Billings-Rockefeller National Historical Park.

A walk around Woodstock Village will make you feel as if you’ve stepped into a Normal Rockwell painting: a kind of quainter, simpler time that many of us long for.

7. Visit the Harpoon and Long Trail Breweries

Sampling Vermont beer is a must-do when traveling in Vermont.

When in Woodstock VT, make the quick 15-minute drive west to the Long Trail Brewery  to try some of Vermont’s most well-known (and well-loved) beers.

Take a brewery tour, then enjoy beer flights or snacks at their Bavarian-inspired pub. There are nice views and delicious brews–what more do you need?

You can also head to Windsor to the Harpoon Brewery.

8. Sample Local Spirits

After you’ve explored the antiques for a while, head down to the end of the shopping center and visit Vermont Spirits. There you can sample Vermont-made whisky, gin, bourbon, and more.

A free tasting lets you try four different spirits. Get ready to feel the burn a bit, but they are delicious. I especially liked the 1791 Cocktail, which had a fruity touch.

9. Learn About Glassblowing at the Simon Pearce Flagship Store

Glassblowing is a popular art in New England. There are many workshops that offer demonstrations, tours, and even lessons.

A really nice place to see glass blowing in action is the Simon Pearce Flagship Store in Quechee . This place features an elegant glassware shop, a glass-blowing studio, and a bar and restaurant.

Head downstairs first to see the glass blowing in action. Several artisans were at work during our Saturday afternoon visit. Though the room is hot and bright, these blowers seemed perfectly relaxed and happy, creating beautiful glass works with ease.

Watching them is hypnotic, but don’t be afraid to ask questions. The artisans are glad to chat with you and educate you on glass blowing.

You can step through onto the balcony to enjoy the refreshing breeze and a view of the nearby covered bridge and tumbling waterfall.

Head back upstairs and browse the wares of the shop. The shining glassware sparkles as you walk through. You will be hard pressed not to purchase some of their amazing glasses and other amazing creations.

Finally, stop for a meal, or even just a cocktail, in their on-site restaurant. The food here is divine and the atmosphere the perfect blend of relaxation and luxury. 

Trust me: get their Vermont cheese soup! Drool! If you time your meal right, you might be lucky and get one of the tables overlooking the tumbling water outside!

10. Explore a Quaint Bookshop

In Woodstock, we saw a sign for used books and had to stop. This eclectic bookstore, Pleasant Street Book Store, had lots of volumes old and new and was a fun place to browse.

They also had a nice view over the river from behind the shop.

When searching for what to do in Woodstock VT, don’t discount those hidden gems that you just might stumble across. However, if you’re keen to visit, try to call ahead as the open hours seem to vary.

11. Visit the raptors at VINS

The Vermont Institute of Natural Science (VINS) is a must-do on your Woodstock bucket list, particularly if you’re traveling with kids!

VINS is an organization dedicated to avian rehabilitation and environmental conservation. Every visit there is not only a fun, cool experience seeing birds up close, it’s a lesson in how to better care for our earth and its inhabitants.

We visited VINS with our one-year-old son recently, and while he threw passing glances at the Snowy Owls and the sharp-eyed hawk varieties, my husband and I were fascinated. 

VINS takes in birds who have been injured and nurses them back to health to be released, if possible. If that is not possible, or they are otherwise unfit for life in the wild, they may stay on at VINS as animal ambassadors. 

When you visit VINS you can see a dozen or more of these amazing raptors in their large enclosures. Throughout the day, staff gives various lectures and programs that allow you to see the raptors in action and learn about them in more detail.

It was pretty exciting when one of their hawks flew right over my head!

After hanging with your new feathered friends, you won’t want to miss the Forest Canopy Walk, which is relatively new to VINS. 

This impressive wooden walkway takes you 100 feet or more over the forest floor, near the bank of the Ottauquechee River.

While there are some parts of the Canopy Walk only accessible by stairs, such as the Eagle’s Nest and the Tree House, the majority of the path is an ADA-accessible boardwalk, and we took my son on the walk in his stroller with ease.

12. Take a Hike

There are numerous options for lovely hiking near Woodstock, VT. 

The majority of local hiking trails lie within the Marsh – Billings – Rockefeller National Historical Park. Yes, that’s right! There is a National Park in Vermont! 

This scenic property is home to miles of trails and carriage roads, offering opportunities for outdoor recreation in abundance.

Mount Tom is your #1 choice for a short yet very scenic hike. This peak will reward you with views over the town of Woodstock and the distant Green Mountains.

My friend Tara at Vermont Explored has a guide for an ideal easy to moderate hike of Mount Tom and the Pogue .

Want to get out and about for some hiking in the area? This resource for local hiking trails will tell you all you need to know.

You can also check out our article on the best Vermont hiking trails, for options near to Woodstock and farther afield. 

13. Enjoy the Ottauquechee River

The Ottaquechee River brings this region together, and it’s something not to miss. Of course, you won’t really be able to since it’s right there!

One of the best ways to make the most of Woodstock’s pretty river is by sitting and relaxing on its banks. If you stay at a hotel located on the river, you’ll have a perfect spot to do so, as my family and I did when we stayed at 506 on The River Inn last summer.

Hop into one of those appealing Adirondack chairs and watch the world go by. 

14. Catch Some Classic New England Architecture

Covered bridges? Check! Stately Vermont homes? Check! White steepled churches? Check check check!

There’s no shortage of classic New England architecture in Woodstock, Vermont.

A walk around downtown Woodstock will introduce you to much of this quintessential architecture, but don’t just stick to the main road.

Venture off into the nearby residential areas. The stately homes are beautiful, and during one of my visits to Woodstock in July, the homes were draped with red, white, and blue banners and flying many American flags.

Classic New England at its finest!

As you explore Woodstock’s Main Street area, don’t miss a look at the iconic Woodstock Inn. The lawn and flowers in front of the inn are always a treat, and this is absolutely an example of quintessential New England charm. 

15. Visit Farmhouse Pottery

This Woodstock Vermont shop is America’s largest studio pottery workshop , and in addition to their stunning selection of pottery homeware, they also offer “Clay Dates” where you can handcraft your own piece right alongside a master potter. This would be a very unique Woodstock, VT souvenir!

16. Check in With the Woodstock, VT Events Calendar

If you’re looking for things to do in Woodstock, VT this weekend or on any other specific date, be sure to check in with the Woodstock VT events calendar !

How else would you know that National Ice Cream Day is being celebrated at Billings Farm and Museum in July?

Woodstock, VT Fall Activities

17. experience woodstock vermont fall foliage.

There are many online foliage maps that you can reference to align your travel with the autumn colors, but fall in Woodstock generally is at its best in mid to late September and early October. Let’s start with something everyone wants to know: what is there to do in in the fall in Woodstock? The answer: PLENTY!

Fall in Vermont is nothing short of epic, and towns like Woodstock are absolutely ideal for leaf-peeping fun! In fact, Woodstock is on my recommended New England fall road trip itinerary .

There are so many great ways to get out and enjoy the beauty of the blazing Vermont fall foliage, whether you’re hiking, strolling downtown, or just going for a leisurely country drive!

Important Note for 2023! You may have seen in other guides for things to do in Woodstock or in countless influencer images on Instagram, a certain photogenic farm recommended. This is called Sleepy Hollow farm and in recent years has gained extreme popularity. Unfortunately, the popularity has gone too far. This farm is private property and situated on a small country road. Sadly, the inundation of tourists trying to catch a glimpse of the farm has created a number of issues, including major traffic concerns on this residential road. There has also apparently been many instances of visitors trespassing on the property and being disrespectful of this property as well as neighbors’. In 2023, residents of the area have worked together to close this road to the public during the height of fall foliage season. So, please do not attempt to visit Sleepy Hollow Farm this fall. And even when the road is reopened, I would strongly discourage you from visiting. Instead, please consider visiting one of the many public, local farms that would welcome you! These include Sugarbush Farm, Billings Farm, and others. And PS: while Sleepy Hollow is scenic, there are literally thousands of gorgeous properties in Vermont you could see with the same beautiful autumn magic. So go drive down some back roads and explore a bit. And remember, always respect private property.

18. Go apple picking

When it comes to fall in Vermont, there may be nothing more iconic than apple picking. One of the best things you can do when visiting Woodstock during this season is to head to a nearby orchard and pick-your-own apples. A few local options to consider include Whitman Brook Orchard in Quechee, and Moore’s Orchards in North Pomfret.

19. Take a fall picnic atop Mt. Peg

Get into Vermont nature with a hike on the Mount Peg Loop , a 1.3 mile trail that offers lovely views for a relatively short journey. I suggest grabbing sandwiches from Mon Vert Cafe for your picnic!

20. Take a day trip to a nearby pumpkin patch

Your fall trip to Woodstock wouldn’t be complete without another quintessential fall activity. Fortunately, Vermont is abounding in farms, so you won’t have trouble finding a festive spot to grab a pumpkin.

In Woodstock, On the Edge Farm is a great option. It’s not a traditional pumpkin patch, but an oh-so-cute farm stand in a picture-perfect setting. You can get pumpkins, flowers, pies, and more.

Woodstock, VT Winter Activities

21. experience a classic woodstock vermont christmas.

If you’re looking to experience a New England Christmas that goes all in on charm, then you need to plan to visit Woodstock VT for Christmas!

Wassail Weekend in Woodstock is the undisputed star of the Christmas season, and with good reason: carriage rides through downtown Woodstock, historic homes decorated to the nines, and music festivities all around town are just a few of the things that make a plan to visit Woodstock VT for Christmas a must for anyone looking for quaint Woodstock VT activities!

22. Hit the Slopes at Saskadena Six

Saskadena Six is one of the country’s oldest ski resorts, and it’s absolutely one of the best things to do near Woodstock VT!

Located just 5 minutes up the road in Pomfret, Saskadena Six is the place to go for outdoor adventures in summer or winter; play in the snow on the mountain while skiing or snowboarding, or embrace a Woodstock Vermont summer by participating in guided mountain bike tours, hikes, and more in this absolutely gorgeous outdoor space!

Woodstock, VT Spring Activities

23. welcome baby animals at billings farm.

A visit to Billings Farm is one of the best things to do in Woodstock, VT throughout the year. But if your visit is in the springtime, you can’t miss the Baby Farm Animal Celebration.

This event happens one day each year, and it is very special. Visitors can meet chicks and ducklings, pet baby lambs and goats, and participate in a variety of other activities including wagon rides and crafts.

This is a fantastic family-friendly event and it is a perfect way to celebrate the season of spring: welcoming new life into the Green Mountains!

24. Sift Through Endless Antiques

New England is a great place to go antiquing. I’m always surprised at the number of antique shops to be found all over Vermont and New Hampshire.

Well, if you love searching for treasures of the past, we found the trove. In Quechee Gorge Village (the same place where you can sample Cabot cheese) is an enormous antiques mall with several floors filled with antique items of all kinds.

It’s a fascinating place to walk around in. On our recent trip to Woodstock, we ran into some bad weather–exploring this antiques mall was a perfect rainy-day activity!

Woodstock, VT Summer Activities

25. attend the quechee balloon festival.

Every summer, the Quechee Balloon Festival comes to town. The longest running hot air balloon festival in New England, this is a must-attend event. You’ll have the chance to see dozens of colorful balloons in flight over the serene Vermont landscape.

You can also book for balloon rides (traditional ascension flights or tethered rides) but be aware that these book up well in advance! Next year’s Quechee Balloon Festival will be held June 14-16, 2024.

26. Learn the art of falconry

Have you ever wanted to handle a hawk? Learn how to hold an owl on your arm and then let it fly? This is something that is a total dream for me, so on my next visit to Woodstock, I am signing up for a session with New England Falconry . Your lesson in falconry with a master falconer will be an unforgettable experience. They offer a few different sessions, so you can take your pick of working with and learning about hawks, owls, and even eagles. While this is an awesome thing to do in Woodstock throughout the year, their more extensive sessions with owls and eagles are only offered April through August, so summer is prime time for this activity.

Is Woodstock, VT Worth Visiting?

Woodstock, VT is absolutely worth visiting, betweens its fall foliage, small town charm, and many things to do. If I haven’t convinced you yet, I’m doubling down to tell you YES: you should plan a trip to one of my favorite places to visit in Vermont.

When is the best time to visit Woodstock, Vermont?

The first question many Vermont visitors ask is “when should I visit Woodstock?” 

Fortunately, Woodstock is beautiful in all seasons. I’m going to share some suggestions on the best things to do in each season in a bit. Although late winter and what is sometimes called “stick season” here in Vermont is admittedly less magical.

But fall and winter are probably the standouts for most visitors, and I agree! Far and away the best time to visit Woodstock, VT is in the fall or the winter.

Woodstock has consistently been named one of the best places to visit at Christmas and one of the most beautiful towns in America. 

It consistently tops list of Vermont fall foliage locations not to be missed. People adore fall in Woodstock, with all its color and charm.

Where is Woodstock, VT?

If you’re wondering where Woodstock, Vermont is located, it’s in the east-central area of Vermont, roughly 15 miles from the western border of New Hampshire.

It’s an essential stop on a Vermont road trip , and an easy day trip from other Vermont destinations, such as Burlington , Stowe , and Manchester .

How To Get to Woodstock, VT

To get to Woodstock, you’ll need a car. The cities of Boston, MA, Albany, NY and Portland, ME are all within a drive of two to three hours. The cities of Burlington, VT and Manchester, NH are about 90 minutes away by car. All of these cities have major airports, with Boston offering the most flight options.

Places to Stay in Woodstock, VT

After a day spent adventuring around lovely Woodstock, what could be better than a wonderful spot to rest your head? There are plenty of great hotels in Woodstock, VT to choose from, and I have a couple of recommendations, depending on what you’re looking for.

The Woodstock Inn

If you’re looking for where to stay in Woodstock, VT, consider The Woodstock Inn and Resort, an exquisite property that hosts beautiful weddings; the onsite spa is considered one of the best things to do in Woodstock VT to unwind!

A stay here is definitely more of a splurge, but it is a great option for a romantic getaway in Woodstock, VT. Click here to check the latest prices and availability .

The Jackson House Inn

Another one of the hotels in Woodstock, Vermont you might choose is the Jackson House Inn. For those seeking a classic Vermont bed and breakfast experience, this is a terrific choice.

The inn is located a few miles from downtown Woodstock, providing a more country feel. Click here to check prices and availability .

The Sleep Woodstock Motel

For the budget conscious, there can be no better choice than the Sleep Woodstock Motel . In fact, this is an all-around excellent option for hotels in Woodstock Vermont! The prices are reasonable, especially since the motel feels a bit upscale.

Sleep Woodstock is a newer addition to the Woodstock area, and it is a good one as this region doesn’t have too many budget-friendly accommodation choices. Clean, cute, and homey, the Sleep Woodstock has the vibe of a 1950s motor lodge combined with the touches of a modern hotel.

My husband and I were hosted here during one of our trips to Woodstock, and we really, really loved it. The room was spacious, every feature was brand new, and the bed provided one of the most comfortable nights of sleep ever!

Our room had a fridge and microwave, too: very convenient for chilling our wine.

To top it off, the motel’s owner, Patrick, is super friendly and ready to give you tons of suggestions for things to do around Woodstock, VT, especially where to grab the best food.

We absolutely recommend Sleep Woodstock for couples, families, and other travelers. It’s an affordable motel in Woodstock, VT in a great location. Click here to check prices and availability .

Fat Sheep Farm

For a unique place to stay near Woodstock, VT, consider Fat Sheep Farm in nearby Hartland, just about a 20 minute drive from Woodstock. Fat Sheep Farm is a working farm that also offers cozy cabins for rent on this sprawling 60-acre property. For a taste of working farm life- because yes, you do get to help tend to the animals!- there’s no better opportunity than a stay at one of the coolest places to stay near Woodstock!

Check out our experience at Fat Sheep Farm here !

Where to Eat in Woodstock Vermont

There are plenty of restaurants in Woodstock, VT that beckon you to try them. Unfortunately, you’ll never get to them all in a single visit, but you can get a good sample!

When time is limited, we recommend checking out these great restaurants in Woodstock:

Eat Farm-to-Table Goodness – Cloudland Farm

You can’t miss out on farm-to-table dining in VT. The state’s immense farmland has inspired countless restaurants that use crops, meat, and more straight from the source.

One Woodstock Vermont restaurant that should be on the top of your list is Cloudland Farm. This farm-to-table operation is absolutely divine.

Cloudland Farm is found up a winding set of beautiful VT roads. The route is so woodsy that you might feel as if you’ve taken a wrong turn, but you’re on the right track. Around a final bend, you’ll see the sprawling property overlooking a stunning mountain vista.

Before your meal begins, you can sit on the veranda and simply take in the view with a glass of wine. It’s so relaxing and romantic. (Cloudland is BYOB, so plan ahead and bring along your favorite bottle of wine or a selection of beers.)

Then, it’s time for your dinner.

Get ready for an incredible meal. Each night’s menu is different, with chef-selected daily fare crafted entirely from local ingredients.

A list on your table tells you where each item has been sourced. Cloudland partners with an impressive number of farms in Vermont, New Hampshire, and even Massachusetts.

The entree at Cloudland was braised pork (raised right at Cloudland itself), herb mashed potatoes, with a rhubarb compote and a berry glaze. My husband had this, while I had a vegetarian option: risotto cakes, also with fresh rhubarb and a local egg.

Both dishes were phenomenal, served with a fresh green salad to start and finished off with strawberry crepes and basil ice cream. The entire experience was lovely, and the food flavors were brilliantly paired.

The waitstaff is great, and your dinner feels personalized and special. We highly recommend Cloudland for fine dining in Woodstock, VT.

Coffee and Breakfast in Woodstock, VT – Mon Vert Cafe

As you may know, we really love coffee! Mon Vert has excellent coffee options in a hip downtown cafe. But it’s their breakfast that keeps guests coming again and again. Wow!

We dined on fruit-topped french toast and classic biscuits and gravy. We were stuffed to the gills after our meal, but we were so, so content.

My must-order item whenever I visit Mon Vert is a maple latte. Bliss.

The staff here is amazingly friendly and down-to-earth, something that can really take a coffee shop or restaurant to the next level. 10/10 highly recommend! 🙂

Like Cloudland, Mon Vert Cafe also relies heavily on local farms and suppliers. No doubt, this is one of the reasons the food is so awesome.

More Coffee in Woodstock – Abracadabra

Another great place for coffee in Woodstock is a newer spot, Abracadabra Coffee Company. I stopped here on my most recent visit to Woodstock and it’s such a great addition to the area! As their website says, they offer “SEASONALLY SOURCED SLAMMIN’ SINGLE ORIGIN COFFEES SINCE DAY 1”. I had my usual here (a maple latte, of course) and it was terrific!

Plus, their location is fun: they’ve got a ’64 Shasta coffee trailer parked inside the shop, and the vibes are just awesome. You can find Abracadabra outside of downtown Woodstock, a few minutes up Route 12 at 35 Wayside Road. Open 6 days a week, closed Tuesdays.

Tasty Dinner in Woodstock – Worthy Kitchen

Another of the best restaurants Woodstock has to offer is found a bit east of downtown.

In an unassuming brown building, you’ll find the delicious Worthy Kitchen, a super casual eatery that is often really crowded–and with good reason. This place is deeeelish.

We ate a Saturday night meal here and had a tough time choosing what to order. Eventually, Nathan opted for a brisket sandwich, and I went classic–a cheeseburger. Both were excellent and served with good fries.

Don’t miss the nice local beer menu, either.

More Vermont travel planning here:

• 12 Fun Things To Do in Brattleboro VT
• Top 12 Fun Things to do in Killington VT

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16 Incredible Things to Do in Woodstock VT (2024 Guide)

Searching for the best things to do in Woodstock VT? You’ve ended up in the perfect place to find all the inspiration and travel advice you need!

Did you know that Woodstock VT is considered the prettiest town in the US? Multiple publications share that sentiment which is saying something!

Although this photogenic town is compact and small, that’s not to say there aren’t masses to keep you busy. Plus, the farmland, forests, and state parks surrounding Woodstock are essential to factor into your plans.

So where to go and what to do in Woodstock? Read on for the complete list of the best places to visit in Woodstock VT plus essential advice for planning your trip.

* Disclosure: This post contains a few affiliate links, which means I may receive a small commission, at no cost to you, if you make a purchase through my link. *

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Table of Contents

Useful Info for Visiting Woodstock VT

How to get to woodstock, vermont.

Officially speaking, Lebanon Airport (LEB) is the closest airport to Woodstock. It’s located 15 miles (24 km) to the east in the state of New Hampshire. However, you’ll find that flights from international airports require transit via a larger port.

Burlington International Airport (BTV) is well-served by national US cities. If you are planning what to do in Woodstock within a wider New England road trip then you could always start here in northern Vermont.

In terms of the best option for travelers beyond the US, your best bet is Boston Logan International Airport (BOS). Located in the city of Boston, Massachusetts, this large airport is the best place to start your search for flights from Europe and other worldwide destinations.

Best time to visit Woodstock, Vermont

Woodstock is a year-round destination where each season brings a new selection of activities to choose from. 

In terms of scenery, places to visit in Woodstock VT are particularly special during the fall season when the foliage turns to hues of gold, amber, and scarlet. Bear in mind that this is a popular time to visit Vermont and New England so you will need to book accommodation in advance.

Mid-spring and early summer is a great time to visit Woodstock if you want to explore the local hiking trails and beat the summer rush. 

Meanwhile, the winter snowfall is perfect for skiers, snowboarders, and sledding enthusiasts. Remember that most state parks and some roads are closed to the public during winter. You may need to rent a 4X4 and take into account other seasonal precautions in order to drive safely. 

How to get around Woodstock VT

Woodstock town itself is walkable and there are a handful of sights to see in the center. However, the best things to do in Woodstock VT aren’t always constrained to the town center!

Realistically, you will need to hire a car in order to explore the area around Woodstock. Public transportation in the New England region is limited and taxis are costly if you want to explore the surrounding towns and parks. 

Roads around Woodstock are in fantastic condition while parking is aplenty, so hiring a car and driving around this beautiful area is a blast.

Where to stay in Woodstock, Vermont

Hotels, guest houses, and inns are located in the town center of Woodstock as well as the surrounding area.

If you stay in town, you can enjoy having the restaurants and amenities on your doorstep with no need to drive. Staying further afield is perfect if you want more of a countryside vibe. 

A word of warning: places in Woodstock VT get booked up months in advance so you’ll definitely need to organize yourself in plenty of time. This is especially true if you visit during summer or the fall foliage season!

LUXURY – 506 On the River Inn Woodstock

Centrally located with an indoor swimming pool and sauna, this is the perfect luxury base for your Woodstock VT activities. All boutique rooms are fitted with a private balcony and en suite bathroom. Studios come with a personal kitchen. 

MID-RANGE – The Shire Woodstock

This pet-friendly hotel is situated on the banks of the Ottauquechee River. Each guest room is appointed with traditional New England furnishings and many offer a river view. Scenic, comfortable, and convenient!

BUDGET – The Vesper Woodstock

Located just off the Village Green, this Greek Revival home is furnished with antiques, oriental rugs, and a collection of art. Rooms are bright and cheerful with a private bathroom. Breakfast is included in the rate.

Best Things to Do in Woodstock VT

Let’s dive into the main part of the guide – all the fabulous and unforgettable things to do in Woodstock Vermont!

1. Explore Woodstock Central Street and The Green

The heart of Woodstock is defined by Central Street and The Green. This walkable center is bursting with cafes, restaurants, and small independent boutiques where you can pick up books, jewelry, and trinkets. 

Whatever you do, make sure that unwinding with a coffee is one of the high-priority things to do in Woodstock VT!

Dishing up organic breakfasts and excellent coffee, Mont Vert Cafe features a gorgeous patio as well as a homely interior. Right next door, Soulfully Good Coffee is the place to go when you’re craving waffles, croissants, and freshly baked treats. 

Have a wander down to the Woodstock Town Hall Theatre. Originally an opera house, this neoclassical manor now hosts a variety of musical events as well as performance theater and movie screenings.

It’s worth checking the schedule to coincide with your trip in case you fancy doing something fun in the evening. 

2. Tour the Woodstock History Center

This is one of the first places to visit in Woodstock VT in order to get a handle on the local and regional history. Exhibits change frequently and tell the story of the people that have dwelled in and shaped Woodstock.

Artifacts on display include paintings, photographs, books, and objects. It’s a small collection but utterly worth a visit so that you understand more about the area.

The Woodstock History Center is located on Central Street and is open from Monday to Friday. 

3. Walk to Woodstock Middle Covered Bridge 

Vermont and the wider New England region are famous for their covered bridges. These historic structures were, on the whole, constructed during the 19th and 20th centuries. 

There were several reasons behind their construction. For starters, they averted the risk of flooding caused by heavy snowfall in the region.

Additionally, they would provide safe shelter for pedestrians caught in storms and make local farmers’ lives easier when herding livestock. 

Now – in the 21st century – these relics from the past have blossomed as major tourist attractions. The Woodstock Middle Covered Bridge staddles the Ottauquechee River and is one of the most beautiful bridges of its kind in the region. 

This one was only built in 1969 although the engineers used historic techniques in order to replace the original bridge. The result is that it looks a lot older than you might think! This bridge is special as it features a separate walkway for passengers to walk safely alongside motor vehicles. 

Best of all, this is one of the Woodstock VT attractions that you can visit in town without the need for a car. 

Read More: 17 Incredible Covered Bridges in Vermont You Need to Visit

4. Stock up at the Woodstock Farmers Market

Woodstock Farmers Market is located one mile west of the town. It’s open Tuesday through Saturday (closed on Mondays and Sundays) and is attached to a seasonal garden center.

The market sells fresh grocery produce, dairy and eggs, meat and seafood, baked goods, and specialty pantry items. Everything is sourced and produced in the Woodstock area and Vermont. You also pick up pre-made artisanal sandwiches to go. 

The farmer’s market opens at 8 am and it’s a great place to pick up your essentials before embarking on a day trip while supporting local businesses.  

5. Snap a sunrise photo of Sleepy Hollow Farm

Sleepy Hollow Farm is a private farmstead consisting of russet-red outhouses and barns just outside of the town. This photogenic farm is set against a backdrop of Vermont hills and forestry. 

Its first recorded owners were a pair of brothers from the 18th century. After a couple of centuries of work, the last surviving relatives ended up selling the farm in the 1950s.

For a couple of years, Sleepy Hollow passed through a series of hands. It continues to be privately owned, however, it is possible to drive up to the premises and take photos.

As one of the most popular things to see in Woodstock VT, you should arrive there first thing in the morning if you want to avoid a long line of cars. This is especially true if you ’re visiting Vermont in the fall !

​​Sleepy Hollow Farm is located a 15-minute drive north of Woodstock on Cloudland Road – a long gravel dirt track that winds through the countryside.

2023 UPDATE: Unfortunately, access to Cloudland Road will be limited to locals only starting from 23 September to 15 October, so if you’re visiting during this period, you won’t be able to see the farm in person.

6. Sample cheese and maple syrup at Sugarbush Farm

Another farm to add to your list of things to do near Woodstock VT! Sugarbush Farm is a 500-acre farm owned by a local family that produces some of the best cheeses and maple syrups in the area.

The Luce family eagerly welcomes visitors to tour the farm, walk the nature trail through the woodlands, and browse the farm shop. Workshops operate an open-door policy so you can pop in and see how the cheeses and syrups are made. Not to mention, tastings!

It’s free to visit Sugarbush Farm although it’s polite to make a purchase from the farm shop to support the business. 

Sugarbush Farm is located a 15-minute drive out of Woodstock. 

7. Swing by the Instagrammable Jenne Road Farm

The next farm to add to your radar is super famous on social media. 

Jenne Road Farm consists of scarlet-hued outhouses and barns. This working farm is owned by a local family and has been in operation since the early 20th century.

Unfortunately, you can’t visit the farm properly and look around but you are permitted to stop by for a quick photo. Plus, you can pick up some of their maple syrup while passing through. 

Jenne Road Farm is one of the major Woodstock VT attractions to visit during fall when the colors dance behind the buildings. 

The farm is located 15-minutes south of Woodstock, off State Route 106. 

8. Explore Billings Park and Mount Tom

When you’re seeking outdoor and hiking pursuits, Mount Tom is the closest option to the Woodstock center.

The peak is located in Billings Park – a large green space that also contains the Marsh-Billings-Rockefeller National Historical Park. There are multiple hiking trails and walking paths within this complex of varying difficulty.

Mount Tom is accessible via a moderate 4-mile hike. The route has a noticeable elevation that your legs will feel although it’s not too challenging overall.

Once at the top, you’ll have a panoramic view across Woodstock. This is particularly special during the fall season when you’ll see all the different hues. 

The summit of Mount Tom is one of the best places to visit in Woodstock VT at sunset. The trail is accessible between April and October before the snow arrives. 

9. Visit the Billings Farm and Museum

Billings Farm and Museum is the final farm on your list of things to do in Woodstock Vermont that is a little different from the others.

For starters, it’s situated in the center of Woodstock so you can walk there easily without the need for a car. This farm is active within the community – it frequently hosts events and runs educational programs with nearby schools.

Tourists are welcome to visit the farm for a token admission fee. Once you’re in, you can wander around the barns, pastures, tractor collection, kitchens, and 1890s farm manager’s lodge. And, of course, befriend the resident animals. 

The farm is dressed with exhibitions and live demos that will enrich your understanding of agricultural practices in Woodstock, Vermont, and New England.

Billings Farm and Museum also offers a robust schedule of seasonal and special events throughout the year. 

10. Take in views from Mount Peg

Located on the opposite side of the Ottauquechee River, Mount Peg is another of the hiking places to visit in Woodstock VT.

It’s located in Billings Park (part two!) and easily accessible via a short and easy hike.

You’ll pass through a copse of woods as well as wide-open meadows before reaching the summit of Mount Peg. There are benches and picnic tables at the top where you can enjoy an al fresco lunch. 

As with Mount Tom, you’ll get a wonderful 360-degree view of Woodstock and appreciate this hike in particular at sunrise or sunset. 

Mount Peg is accessible year-round regardless of the season and it’s perfect for non-hikers as well as families with younger children.

11. Hike in Quechee State Park

Quechee is a small town located a 10-minute drive east of Woodstock. Its town center warrants a wander (especially so that you can see the Quechee Covered Bridge) but the highlight of Quechee is the state park.

Park up at the Quechee Gorge Bridge and take a look at the gorge known as Vermont’s “Little Grand Canyon”. 

Carved by glaciers during the last Ice Age, the gorge has a depth of 165 feet (50 meters). You can view it from the bridge and swing by the Quechee Gorge Visitor’s Center to see the exhibits on its history. 

While there, pick up some hiking maps for the state park. Quechee State Park is one of the best things to do near Woodstock VT for outdoors lovers. Trails take you through the forest surrounding the gorge and provide different viewpoints of the natural wonder. 

Quechee State Park is open seasonally, May through October. Check the specific dates for each year if you want to visit Vermont to see the fall as well as hit the state park!

12. Explore Coolidge State Park

Vermont’s largest state park is located 12 miles (19 km) to the southwest of Woodstock. As with Quechee State Park, the park is open exclusively from May until October. 

Hiking trails in the Coolidge State Park navigate various peaks and lead you to dramatic views across the Black River Valley and the Green Mountains.

There are a number of pools, reservoirs, and brooks which are perfect for helping you to cool down during the summer season. 

The forest provides a habitat for the likes of barred owls, moose, and even black bears. 

Coolidge State Park is known for its fantastic campgrounds so if you fancy spending a night in the wilderness while in Woodstock, this is the perfect place. There is a mix of campsites and RV hook-ups. 

13. Nibble on local cheese

All these sightseeing and outdoorsy activities will build up an appetite. If you like cheese, you’ll be right at home in Woodstock. The town is known for its cheeses and one of the top things to do in Woodstock VT is finding your favorite. 

I’ve already mentioned Billings Farm and the Woodstock Farmer’s Market which are two of the best places to try cheese in Woodstock. You can also visit Mac’s Woodstock Market , F. H. Gillingham & Sons , and the Vermont Farmstead Cheese Company . 

The latter is further out of town but it’s worth the drive if you’re a huge fan of trying different cheese varieties. 

14. Eat the best ice cream

Mountain Creamery is a small, independently owned ice cream parlor located a short drive out of Woodstock VT.

All ice cream is handmade and uses local flavors from the Vermont region, such as maple syrup and walnuts. You can create your own sundae to suit your tastes and add toppings such as Oreo cookies, Reeses Pieces, and fresh fruits. 

If you’re not a fan of ice cream, they also serve pies, smoothies, and frappes. 

The Mountain Creamery is a 10-minute drive from the Village Green. However, if you have time in your schedule, you could walk there along the side of the river. This will take around 90 minutes each way though.

15. Drive through Taftsville Covered Bridge

The Middle Covered Bridge is one of the top things to see in Woodstock VT but you might want to visit another bridge while you’re in the area.

Taftsville Covered Bridge is only a 5-minute drive east out of Woodstock. This is another structure that passed over the Ottauquechee River. It’s a vibrant shade of red and really stands out against the backdrop of green (or orange) trees. 

Constructed in 1836, the Taftsville Covered Bridge is actually one of the oldest of its kind in New England.

You can drive beneath it in your car but it’s worth parking up and wandering down to the riverside where you can see the waterfall that drops below the bridge.

16. Wind down in a Vermont brewery

And what to do in Woodstock if you love beer? Vermont is famed for its craft beers and fortunately, there are a couple of breweries within easy access of Woodstock VT.

Founded in 1989, Long Tail Brewing Company is located on the banks of the Ottauquechee River and provides a lovely setting to sip the latest selection.

The brand was inspired by the 273-mile (440 km) hiking trail that traverses through the nearby Green Mountains. They specialize in IPAs and you can buy their flagship selection year-round but they also craft seasonal blends.

Long Trail Brewing Company is a 10-15 minute drive from Woodstock. 

Harpoon Brewery Taproom and Beer Garden is located at the side of the Connecticut River and overlooks New Hampshire.

They have a huge beer garden which is perfect in the summertime while their heated cabins are preferential if you visit during winter. Beers are a mix of ales and lagers as well as ciders. Harpoon Brewery is known for its excellent woodfired pizzas and events. 

Situated in Windsor, Harpoon Brewery Taproom and Beer Garden is a 20-25 minute drive from Woodstock VT. 

Planning a trip to New England?

Then you might want to take a look at all our other travel guides about New England. I promise, they are just as awesome as this article was!

• The Perfect New England Fall Road Trip for 2 Weeks
• Vermont in the Fall: Travel Tips & Best Places to Visit
• 16 Incredible Things to Do in Woodstock VT
• 17 Amazing Things to Do in Stowe, Vermont
• 17 Incredible Covered Bridges in Vermont You Need to Visit
• 81 Amazing Vermont Quotes & Captions for Instagram

New Hampshire:

• Kancamagus Highway Fall Foliage Drive: 9 Best Attractions & Tips for Visiting

Massachusetts:

• How to Spend One Day in Boston: Itinerary & Best Things to Do
• 13 Best Day Trips from Boston You Can’t Miss
• Where to Stay in Boston: 8 Best Areas & Hotels
• 133 Best Boston Captions for Instagram (Quotes, Puns & More)
• 19 Spooky Things to Do in Salem MA in October
• How to Spend One Day in Acadia National Park
• The Perfect 2 Days in Acadia National Park Itinerary
• Acadia National Park in the Fall: Practical Info & Tips for Visiting
• How to Spend One Day in Portland, Maine
• 5 Prettiest Lighthouses in Portland Maine You Can’t Miss

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The Best Things to Do in Vermont in the Fall

By Author Tara Schatz

Posted on Published: August 7, 2023

The Green Mountain State shines in just about every season, but Vermont in the fall is special.

Autumn is when people travel from near and far to get a glimpse of the thrilling carpet of colors that blanket the mountains, forests, and fields starting in late September.

I’ve lived in Vermont for most of my life, and every fall is still a magical experience for me.

Those beautiful fall colors in Vermont sustain me through a winter that is always long and cold and often bleak and grey.

Every year in the fall I make it my mission to drop everything and explore this beautiful state I call home.

I’d love to share some of the things to do in Vermont in the fall before winter opens up a whole new set of opportunities.

I’m based in Southern Vermont , which is a road-trippers paradise, but the whole state deserves some serious explorations.

This guide explores quintessential Vermont fall foliage activities that visitors won’t want to miss and all the best places and things to do in Vermont in the fall.

But first I’d like to answer a few questions about Vermont fall foliage that I receive in multitudes via email or Facebook starting as early as June. 

Psst… Did you know that we run a Facebook group dedicated to all the best things to do in Vermont? It’s particularly active in the fall, as that’s the busiest season in Vermont for tourists. Join the group to ask questions, share photos, and immerse yourself in all things Vermont.

Table of Contents

When is Peak Foliage in Vermont?

This is the million-dollar question! If you are planning your Vermont fall foliage vacation in the summer, you want to know when to book your flight or hotel room so that you don’t miss the prime leaf-peeping season.

In my opinion, it’s better to be a bit early for the fall foliage season in Vermont because you can always go up in elevation to experience more vibrant colors. If you are visiting the mountains, which run north to south through the middle of Vermont, I suggest visiting in early October, especially if you are traveling to the Northeast Kingdom or Stowe.

If you are visiting Southern Vermont, the Lake Champlain Valley, or the Connecticut River Valley for Vermont fall foliage, I would suggest coming during the second week of October.

Unfortunately, Mother Nature doesn’t follow a strict calendar, so there are variations in Vermont fall foliage colors that will depend on temperatures and rainfall.

Based on averages from year-to-year, I would say that the second weekend in October is the sweet spot and the best time to visit Vermont in the fall, but the trend has also skewed toward late colors over the past few years.

Where are the Best Places to See Vermont Fall Foliage?

Another question that I am asked over and over again, is where the best places are to experience Vermont Fall Foliage. Three-quarters of Vermont is covered by forests – vibrant maples, stately oaks, and colorful ash, birch, and larch.

There are so many beautiful back roads in Vermont, and I guess my first suggestion would be to ditch the GPS and pick up a Delorme Gazetteer for Vermont and New Hampshire.  

Some of my favorite back roads to explore are in the Cambridge/Jeffersonville/Underhill area, the Northeast Kingdom, and Bennington County.

Of course, there’s more to Vermont in the fall than colorful leaves. Do you want to hike beautiful Vermont trails ? Visit tourist attractions? Enjoy fall festivals ? The best places to visit in Vermont in the fall depend a lot on what you enjoy doing.

No matter where you go in Vermont, you’ll enjoy small-town hospitality, local treats, and quirky attractions. You can drive from one end of Vermont to the other in under four hours, so if you choose a home base in the north and in the south, you should be able to cover a lot of ground!

Read Next: A 5-Day Fall Foliage Road Trip on Scenic Route 100 in Vermont

If you are interested, I also have a post about the best places to take fall foliage photos in southern Vermont .

One of my favorite back roads to travel on during fall foliage in Vermont is Kelly Stand Road from Arlington to Stratton. I do it every year, stopping at Grout Pond to hike around the lake and capture the fall foliage reflections with my camera.

No matter where you travel in Vermont, you will find fall foliage that will take your breath away, I promise!

The fall foliage season is the most popular time to visit Vermont. It’s a mixed blessing for travelers. On the one hand, Vermont in the fall is incredibly beautiful, and every town and village wants you to visit.

There are festivals, sidewalk sales, and special events all over the state to celebrate autumn in Vermont, and to celebrate you, the traveler who is coming to spend money at local Vermont businesses.

On the other hand, visiting Vermont in the fall means more traffic on back roads, not to mention a harder time booking rooms and making dinner reservations.

Is it worth it? Absolutely! I urge you to immerse yourself in Vermont’s most colorful season and try the following excursions – the best places to go and the best things to do in Vermont in the fall.

Discover Fall in Stowe, Vermont and the Surrounding Communities

Stowe is a small mountain town that attracts visitors year-round, and there are a lot of incredible things to do here in all four seasons.

Winter might be the busiest time in Stowe, thanks to the renowned skiing at Stowe Mountain Resort, but fall is equally appealing in Stowe.

If you are visiting Vermont for a fall vacation and don’t have a lot of time to spend, my suggestion is to make Stowe or nearby Waterbury your home base for the weekend.

While you’re in the area, be sure to check out the mountain towns and villages that make this part of Vermont so special. Drive the back roads and don’t be afraid to get a little lost.

Here are our favorite Vermont fall attractions near Stowe.

Hike or Drive up Mount Mansfield, Vermont’s Tallest Peak

Mount Mansfield got its name because when viewed from the east, it resembles the profile of a giant, sleeping face.

Reaching 4,394 feet at the chin, this is one of only two places in Vermont where you’ll find an arctic-alpine tundra ecosystem, complete with a plethora of tiny, rare plants that can only be found in such high, windswept climates as this – unless, of course, you want to travel to the far reaches of our continent’s northern borders.

More than 40,000 visitors flock to the top of Mount Mansfield each year, and that’s because you can drive to the top on the auto toll road from Stowe Mountain Resort.

This is a fun option if hiking isn’t your thing or you’re in a hurry, but it doesn’t hold a candle to leaves crunching under your boots, and the mesmerizing silence of the forest, blazing with autumn splendor.

There are a few trails up to the top of Mount Mansfield, but I recommend starting in Underhill State Park and hiking the Sunset Ridge Trail. This is a strenuous hike, but the views make it worth every drop of sweat. You can make a loop by combining Sunset Ridge with Vermont’s iconic Long Trai l for a 6-mile loop.

Mount Mansfield is a true gem and one of the most beautiful places to hike during the Vermont fall foliage season.

Looking for an easier hike? Here are some easy and moderate hikes in Stowe with gorgeous views!

Take a Mini Fall Foliage Road Trip through Smuggler’s Notch and Beyond

Not only is Route 108 through Smuggler’s Notch one of the most beautiful roads in the state but it’s got a pretty interesting history too. 

In the early 1800s, the United States Government put an embargo on imports from England. The British started shipping goods to Canada, and smugglers used the caves around the area that is now Smuggler’s Notch Pass to store the booty.

The heavily wooded paths in the Notch made the perfect route for smuggling these goods during the War of 1812.

Fast forward to prohibition and Smuggler’s Notch was again used by smugglers who brought alcohol down from Canada to sell throughout New England. The most well-used path was eventually replaced with a seasonal road.

As long as you aren’t driving a large RV, tour bus, or semi, you can drive up through the Notch. There are places to pull off and explore, plus a few trailheads.

The hike to Bingham Falls starts just across the road from Smuggler’s Notch State Park, and the trailhead to Sterling Pond is right in the Notch. Both hikes are amazing and not too difficult.

For a quick fall foliage road trip that can be completed in about an hour (without stops), take Route 108 north out of Stowe, drive through Smuggler’s Notch, turn right onto Route 15 in Jeffersonville, drive through Johnson, turn right onto Route 100 in Morrisville, and head back into the village of Stowe.

Be sure to stop in all of these adorable villages for shopping, dining, and the friendliest Vermonters!

Smuggler’s Notch is a must-visit attraction in all four seasons, but it’s especially lovely in the fall.

Explore Stowe Village

While you’re in Stowe, be sure to meander around town – it won’t take long. Quaint shops, breweries, and restaurants line the streets, all with a gorgeous mountain backdrop. Stowe is one of the most popular towns to visit in Vermont, and the most beautiful.

In Stowe, visit the Vermont Ski and Snowboard Museum, walk on the Stowe Recreation Path, and hike up to Sunset Rock, for – you guessed it – the sunset. Pop into Black Cap Coffee for lunch or an afternoon espresso, and treat yourself to dinner at Idletyme Brewing (great outdoor seating and fantastic onion rings).

Visit Waterbury, Vermont

Waterbury is even smaller than the town of Stowe, but there are a few awesome spots that you have to visit before leaving the area. It’s located just south of Stowe Village on Route 100.

For beautiful mountain and lake views, visit Waterbury Center State Park . You can hike along Waterbury Reservoir on a short nature trail – 1/2 mile and very easy.

Next, stop at the world-famous Ben & Jerry’s Factory for a tour. Sample some divine ice cream, and be sure to visit the Flavor Graveyard, where you can pay homage to your long-lost ice cream loves.

Not far from Ben & Jerry’s is another iconic spot. Cold Hollow Cider Mill is known for having some of the best cider donuts in the state, not to mention hard and soft cider and an amazing gift shop.

Where to Stay in Stowe or Waterbury in the Fall

• Tälta Lodge Bluebird: Our new favorite place to stay in Stowe, this beautiful lodge is located on the Mountain Road with the river flowing behind the property. You can easily access the Stowe Recreation Path and Smuggler’s Notch is just up the road. Rooms come with an outdoor seating area, and there is an indoor pool and sauna. New for 2023: The Stuga Cottages at Tälta Lodge , which feature private patios, 425 square feet of living space, and a kitchenette.
• The Trapp Family Lodge : The Trapp Family, fictionalized in The Sound of Music , fled Austria during World War II and landed in this beautiful Vermont town. The lodge that you can visit today isn’t the original Trapp Family Lodge, but it’s still a beautiful and historic landmark, with hiking and mountain-biking trails, and lovely accommodations. It’s a perfect jumping-off point for your Vermont vacation.
• Grey Fox Inn : This lovely inn is located within walking distance of shopping and restaurants in Stowe Village. Amenities include indoor and outdoor pools, a hot tub, and a sauna. You can access the Stowe Recreation Path from the property and the views aren’t bad either. Book a room, suite, or condo for your fall foliage vacation.

Explore Burlington, Vermont in the Fall

Burlington, Vermont is about 45 minutes west of Stowe, and another must-visit stop on your fall foliage road trip through Vermont. Burlington is perched on a hill above the expansive waters of Lake Champlain.

Located in a valley with its own microclimate, fall foliage comes a bit later to this part of Vermont. Colors start to turn in mid-October around Burlington and you will likely see beautiful fall foliage into early November.

Burlington is Vermont’s largest city, but it’s still small as far as cities go. While the foliage-viewing opportunities are a bit more limited here, there’s still a lot to see and do.

Here are some of our favorite things to do in Burlington, Vermont in the fall.

Watch a Lake Champlain Sunset over the Adirondacks

A Lake Champlain sunset is just about the most stunning thing I’ve ever seen. No matter how many times I watch the sun sink behind the Adirondacks, turning my favorite lake shades of orange and red, I still catch my breath to glimpse such beauty.

There are lots of places to watch the sunset in Burlington, especially if you’re riding the Burlington Bike Path .

The paved trail hugs the water for most of its eight miles, connecting riders to several lovely parks and beaches. Start in the south end at Oakledge Park, and work your way to North Beach or the mouth of the Winooski River.

You can also catch a pretty amazing sunset from the waterfront right in town or from Oakledge Park, where there are rocky bluffs to perch with a picnic.

Shop till You Drop at the Church Street Marketplace

The bustling Church Street Marketplace is a pedestrian-only shopping and dining area that spans several blocks downtown. Aside from an incredible number of shops, downtown Burlington also has great restaurants and breweries. Here are my recommendations for divine culinary creations in Burlington.

• Coffee and Pastries: August First – You have to try those maple biscuits!
• Breakfast: The Grey Jay on Pearl Street – Fantastic donuts, breakfast sandwiches, and coffee!
• Lunch: The Farmhouse Tap and Grill – Open from 10 am to 10 pm (11 pm on Fridays and Saturdays), The Farmhouse Tap and Grill is the place to go for locally-sourced comfort food and small plates. It’s located in downtown Burlington and only takes reservations for parties of 7 or more.
• Dinner: Honey Road – Eastern Mediterranean fare in a small space. Reservations are a must!

Read Next: Easy Hikes Near Burlington, Vermont

More Places to Visit in Burlington During the Vermont Foliage Season

• The Burlington Farmers’ Market . Every Saturday from 9 to 1. With over 90 vendors and awesome live entertainment, this hoppin’ market is consistently rated as one of the best farmers’ markets in the country. The market is located at 345 Pine Street in the South End.
• The Spirit of Ethan Allen . Get out on Vermont’s biggest lake with a sunset or dinner cruise on the Spirit of Ethan Allen. Cruises depart several times a day from the Burlington Boathouse at the bottom of College Street.
• The ECHO Lake Aquarium and Science Center . This a must if you have kids, but it’s pretty awesome no matter how old you are. Get up close and personal with some of Lake Champlain’s coolest critters, learn about the forces that shaped this beautiful landscape, and check out the awesome traveling exhibits.

Where to Stay in Burlington, Vermont for Fall Foliage

Burlington is a thriving and walkable city, and when it’s within the budget, I always try to reserve a hotel room right downtown so I can walk everywhere. There’s nothing like stepping out of your door in the morning for a brisk waterfront walk or a saunter to the nearest coffee shop.

Hotel Vermont , while on the pricey side, this boutique hotel gets five stars for its location. It’s a stone’s throw from Lake Champlain and close to all of the best downtown shopping and dining. Just remember, you will need to reserve a room far in advance during the fall foliage season.

Hilton Garden Inn : We stayed here for the first time in 2019 and really loved the Main Street location, the funky vibe, and the outdoor fire pit. There is good parking, the beds are comfy, and there’s an indoor pool. Again, reserve early for the best rooms and prices.

If you are visiting Burlington, Vermont in the fall with a family or want something that won’t hit your wallet quite so hard, you may want to reserve an apartment on VRBO.

We have stayed at three downtown apartments in Burlington so far, and have been impressed with all of them. There are short-term rental restrictions in the city of Burlington, so your choices may be limited.

Here’s a quick overview of our favorite Burlington vacation rentals:

• Lakeview Terrace: This is a two-bedroom apartment overlooking Lake Champlain with a fabulous backyard. What more could you want? The Old North End location is perfect for families, and there are lots of parks and playgrounds nearby.
• Renovated South End Carriage House: The Carriage House apartment is a recently renovated space with a private entrance on a quiet residential street. Just a block away from Zero Gravity Brewery, and within walking distance of local beaches and Churchstreet. Sleeps four comfortably.
• One Bedroom Duplex Downtown: Walk to everything from this small one-bedroom apartment with room for four people. Uniquely situated with a private covered deck and off-street parking.

Finally, I have to share one quirky gem with you. The Starlight Inn in Colchester is a movie-themed motel located right next to the iconic Sunset Drive-In Theater. I’ve been catching flicks at the Sunset Drive-Inn since I could walk, and Starlight Inn guests receive complimentary tickets for one car and all its occupants.

Another thing to love about the Starlight Inn? Every room is unique and all of them feature a different movie theme. This is a super fun lodging experience for movie buffs and kids. Colchester is located about 15 minutes from Burlington.

Visit Bennington County, Vermont in the Fall

Of course, I am biased – Bennington, Vermont has been my hometown for the past 16 years, and I believe it’s one of the best places to visit in Vermont in the fall.

Bennington is a small community, with a historic downtown area, beautiful scenery, and lots of opportunities for recreation.

Here are a few things you shouldn’t miss while visiting Bennington, Vermont in the fall.

Explore the Covered Bridges of Bennington County

Vermont boasts more than 100 covered bridges, the highest number per square mile in the United States. Bennington County, in the southwest corner of Vermont, is home to five, all relatively close to each other.

You’ll find three covered bridges in Bennington/North Bennington and two more in Arlington. They all feature authentic construction, but some have been rebuilt over the years. The Arlington bridges are both perched above fabulous swimming holes if you happen to be meandering on a hot, summer day. 

Even if covered bridges aren’t your thing, I urge you to visit this corner of Vermont  in the fall, where you’ll find rolling hills, bustling farm stands, art galleries, museums, and shopping opportunities.

The Appalachian and Long Trails share a single path through these mountains, and both Robert Frost and Norman Rockwell called Bennington County Home at one time. You can even visit Robert Frost’s grave behind the Old First Church in Old Bennington.

Vermont Fall Foliage Sites in Bennington County

• Woodford State Park . It’s true — we’re attracted to out-of-the-way corners, and this is one of our favorite spots for quiet hiking, kayaking, and swimming. Woodford State Park is tucked away in the mountains and sees very few visitors. A quiet lake surrounded by lush forest is the main attraction, but you’ll also find hiking trails and a quiet campground within the park. On really quiet evenings we’ve seen moose and otters, and we hear the fishing is pretty good too.
• Bennington Battle Monument. This is Vermont’s most popular historic site , but we’ve never encountered a full parking lot. Finished in 1891 to commemorate the Battle of Bennington (August 16, 1777), the monument towers 306 feet over the town and is the tallest building in the state. Take a quick elevator ride to the top and enjoy the panoramic views of the town, valleys, and mountains that make this place so special. Don’t forget your camera.
• Lye Brook Falls , Manchester : An easy 2.3-mile hike on a beautiful, forested trail will take you to a lovely waterfall in the Green Mountains. The trail is dog and kid-friendly, and the woods are especially spectacular during fall foliage.
• BATS: The Bennington Area Trail System is a network of trails on the side of Mt. Anthony in Bennington, and you won’t find better views anywhere. Trails range from a walk in the park to steep climbs up the mountain.

Also read: The Best Easy Hikes in Southern Vermont

Where to Stay in Bennington County, Vermont for Fall Foliage

Bennington County has two shires, Manchester in the north and Bennington in the south. It’s about a half-hour drive between the two, so you don’t necessarily want to be hopping between them constantly during your visit. There are lots of lodging choices in both towns.

In Bennington, The Four Chimneys Inn is an iconic New England Inn that will perfectly complement your Vermont fall vacation. Each room is beautifully decorated, breakfast is beyond incredible, and you can walk to all the historic attractions in Old Bennington. 

If you want to hang your hat in Manchester, check out the sprawling Kimpton Taconic Hotel, which is dog-friendly and within walking distance of shopping, dining, and hiking trails in Manchester Village.

Finally, if you want the best of both worlds, stay in this delightful vacation rental in Shaftsbury , between Manchester and Bennington. It has an amazing hot tub, is beautifully decorated, sleeps five, and it’s pet-friendly. This is also one of the most awesome vacation rentals we’ve ever had the pleasure of staying in!

Explore Woodstock, Vermont in the Fall

Woodstock is a quintessential New England Village on the eastern slope of the Green Mountains. This is a busy tourist area, but if you don’t mind leaf-peeping among friendly strangers, you’ll be in good company!

In Woodstock, you can explore five covered bridges, discover Vermont’s only national park, and visit a general store that’s been operating since 1886. This gem of a town makes a great home base while you explore all the best things to do in Vermont in the fall.

Here’s a local’s guide to the best things to do in Woodstock, Vermont in the fall , as well as the neighboring village of Quechee.

We’ve included our favorite tourist attractions, places to stay, and of course, our favorite hiking trails — because we obviously can’t talk about things to do in fall without mentioning our favorite autumn activity. 

Where to Stay in Woodstock, Vermont

Here are our top picks for places to stay in Woodstock and Quechee.

Woodstock Inn & Resort :  This posh resort is located in Woodstock Village, within walking distance of everything downtown. It’s the perfect spot for a special weekend, or fall getaway when you can take advantage of all the best things to do in Woodstock VT.

506 On the River Inn:   Featuring rooms with panoramic river and garden views, 506 On the River Inn features an indoor pool and sauna, gym and kids’ game rooms, and a restaurant.

Log Cabin Apartment in Woodstock:  Walk to everything from this beautiful apartment with room for four guests. This special spot is located in a wooded setting but is just a 1/4-mile to downtown. There’s a full kitchen if you don’t want to dine out in Woodstock.

Historic Cottage on a Vineyard:   A beautiful, 900-square-foot cottage on Gilbert’s Hill with access to hiking trails. The space includes two bedrooms, one bathroom, a full kitchen, and a private deck overlooking the vineyard.

Resources for Visiting Vermont in the Fall

The whole state becomes a tourist attraction during the Vermont fall foliage season, but it’s still worth coming!

If you are planning to visit Vermont during a weekend in October, make your reservations as early as possible. We find the best hotel deals on booking.com or by contacting the hotel directly.

Here are some more resources for planning your Vermont fall foliage vacation:

• Airports: Burlington International Airport is closest to the Champlain Valley, Stowe, and the Northeast Kingdom. If you are traveling to southern Vermont, your best bet is to fly into the Albany International Airport in New York.
• Where to Stay:  Vermont has lots of independent hotels and motels to choose from. If you want more space to spread out, you’ll be happy to know that there are lots of vacation rentals in Vermont for very reasonable rates.
• Vermont Peak Foliage Reports: You can get Vermont fall foliage reports delivered to your inbox by signing up at the Vermont Vacation website .

More Things to Do in Vermont

Grab our five-page printable bucket list that includes all the best things to do in Vermont !

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Tara Schatz is a freelance writer and the founder and editor-in-chief of Vermont Explored and Back Road Ramblers , an American road trip blog. She is also the co-author of the 3rd edition of AMC’s Best Day Hikes in Vermont, released in May 2023, and the author of 100+ Wonderful Ways to Experience Vermont.

Saturday 24th of September 2022

I’m from Hawaii. How can I enjoy in Vermont? Any info will help.

Thursday 11th of August 2022

Which town would you recommend to use as a "base camp" for the last two weeks of Oct. We'll be driving the scenic routes during the day, then park the car and walk to restaurants or pubs in the night.

Tara Schatz

Friday 12th of August 2022

I think you will have the best colors in southern Vermont during the last two weeks of October, so I would look into Bennington, Manchester, or Brattleboro to use as your base camp. All of those will have restaurants and pubs that you can walk to from your lodging.

Sharlene Ansley

Friday 22nd of July 2022

We may be possibly flying in on September 10 leaving 14 th would their be any good fall colors or is that way to early. I really want to make sure we get the most beautiful views because we will probably only get to make the trip once so would that be an okay time or would it be better to plan on a different time

Hi Sharlene - Honestly, I would reschedule for early to mid-October. The foliage will still be pretty green in mid-September, with colors starting to turn in the far north. By early October, the higher elevations and far north will be lovely, and the rest of the state will follow by mid-October. Hope that helps.

Thursday 21st of July 2022

I want to move to Vermont ., buy a large piece of property and build a new traditional home. Do you have contact with a realtor who could contact me. I have been going through different sales, but I like speaking with someone directly. Everything you have been showing and talking about makes me want to buy the whole state of Vermont.

My phone number is 714 536 2743. I live in Huntington Beach, CA. I was originally from Milwaukee, Wisconsin and I have lived here for a very long time always remembering the season changes.

Thanh you in advance for any help you can give me.

Corinne Welch

Thursday 23rd of June 2022

When do the restaurants & shops close for the winter? Also, is Vermont experiencing a labor shortage? Thanks!

Sunday 26th of June 2022

It totally depends on the shops and restaurants. Places that are truly seasonal may close after the second week in October, but lots of places are open year-round as Vermont gets a lot of winter tourists. Yes, we are experiencing a labor shortage and it is affecting the travel/tourism industry.

See Woodstock, Vermont This Fall

The best time to visit Vermont is during the fall months when you’ll be greeted with cool weather and great colors from the fall foliage. It’s something that you will not want to miss. The best place to see the Vermont fall color firsthand is at the  Woodstock Inn & Resort , where we  will give you a front-row seat to fall in  Woodstock, Vermont .

Fall in Vermont's Only National Park

Marsh-Billings-Rockefeller National Historical Park is one of the first places you should visit for fall scenery. The area covers 550 acres of woodlands surrounding the town of Woodstock, Vermont. Accompanying the nature preserve are 20 miles of carriage roads and hiking trails that meander the vistas of nearby Mount Tom . Admission to the National Park is included for Woodstock Inn & Resort guests.

Fall at Billings Farm

A half-mile away from the Woodstock Inn is the Billings Farm & Museum . You can explore the restored 1890 Farm House, wander the heirloom gardens and apple orchard, and join in fun fall events at the Farm! Don't miss the dairy bar terrace with Vermont-made ice cream and the fall treat, apple cider. Admission to the Billings Farm & Museum is included for Woodstock Inn & Resort guests.

See Woodstock, Vermont At Its Most Beautiful

Woodstock, Vermont is a wonderful place in the Fall. There are many exciting and beautiful parks in this small town. Billings Park and  Faulkner Park  include lovely hiking trails and plenty of lush foliage to see. Another great way to soak in fall colors is by walking through the downtown area. Beautiful trees and landscape surround the village, so why not take in the sights with a warm cup of coffee or Vermont hot apple cider to-go?

Don’t forget to take some pictures to share the awe-inspiring beauty of the fall foliage in Woodstock, Vermont when you bring the family to the Woodstock Inn & Resort. You can book directly at the Woodstock Inn & Resort or call 888-338-2745 , and we can tell you more.

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The Best Things to Do in Woodstock,Vermont in the Fall

By Brianna | September 4, 2023

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Woodstock, Vermont is one of those picturesque towns where you can find natural beauty and fun things to do year round, but I think autumn is when it is at its most gorgeous. If you’re looking for things to do in Woodstock VT in the fall, you’ve got so much to look forward to. Crisp autumn air, charming town festivals, and of course, fall foliage colors provide the most scenic backdrop. If you’re ready to plan your fall trip to Woodstock, Vermont trip then autumn fun awaits!

This post contains affiliate links. The Casual Travelist receives a small commission for any purchases made through these links at no additional cost to you .

Things to Do in Woodstock VT in the Fall

With natural beauty and small town charm Woodstock is one of the best fall destinations in the United States . Discover the best things to do in Woodstock on your next fall vacation.

Swing by Mon Vert Cafe for a Coffee

Mon Vert Cafe is one of the cutest cafes in Woodstock, Vermont with excellent coffee and delish menu options. This cafe definitely has a nice local Vermont feel, with locally sourced ingredients, a friendly staff, and a comfy, cozy vibe that’s perfect for a fall cup of coffee. They use Vermont Coffee Company grounds, so it’s hard to go wrong when you start with quality beans like that. Mon Vert Cafe is open for breakfast and lunch. Their French Toast is phenomenal!

Explore Downtown Woodstock

One of the most essential items on this list is to explore one of the most charming areas of Woodstock: downtown! There are a variety of great shops, bookstores, and restaurants, but one of the must visit spots is F.H. Gillingham & Sons . Gillingham’s General Store is one of Vermont’s oldest family owned general stores, and it’s been a staple of downtown Woodstock since 1886. You’ll find a little of everything (and a ton of great souvenir options) from clothing to maple syrup, to Vermont cheese and so much more. This is one of those places you really can’t skip over during a Woodstock trip and it also is the perfect place to pack a little picnic basket for your Woodstock explorations.

Take in the Fall Foliage Views from Mount Peg

Conveniently, the hike to the summit of Mount Peg begins right in the heart of Woodstock Village. Begining on Golf Street this is a 2.5 mile round trip hike it is a quick, somewhat steep trail. This isn’t a strenuous hike by any means, but you’ll be ready to relax and take in those views once you reach the summit. There also happens to be a picnic table and a few benches at the top, so you can comfortably enjoy your snacks from Gillingham’s while marveling at the panoramic views of Vermont fall foliage that stretch out beneath you. The rolling hills awash in autumn colors of gold and red are breathtaking from this vantage point, and this is a great spot for some fall foliage photography.

Go Apple Picking at Whitman Brook Orchard

Located in nearby Quechee, Whitman Brook Orchard is the perfect place near Woodstock to go pick your own apples. Apple picking is a quintessential fall activity for the region, and Whitman Brook Orchard has over 140 varieties of apples on this stunning property, and their “you pick” apple orchard is just waiting for you to come on out and explore.

Explore Sugarbush Farm

You likely already know how important maple syrup is to the Green Mountain State, but a visit to a working sugarhouse puts it in an entirely new perspective. Sugaring season is in the spring, but Sugarbush Farm converts their sugar house into an educational display during the off months, with an educational video and exhibits that illuminate how maple syrup is made. There are also farm animals, nature trails, a country store, and plenty of space on this 500 acre farm to enjoy the fantastic fall foliage. Open until 5pm each day, be sure to make it out to this Woodstock gem.

Photograph Woodstock Covered Bridges

One of the most charming aspects of visiting New England is stumbling upon covered bridges. There are four covered bridges in the Woodstock area that you should be on the lookout for, with Middle Covered Bridge being the most popular due to its location right off the village green. Bright red Taftsville Covered Bridge is another very popular Woodstock covered bridge, and it is one of the oldest covered bridges in the US. Lincoln Covered Bridge and Queechee covered bridge are the other two most popular bridges in the Woodstock area, and truth be told every single one on this list is photogenic with a ton of classic Vermont charm — especially when the fall foliage colors around them offer the perfect backdrop.

Indulge in Dinner at Cloudland Farm

Dinner is served at Cloudland Farm Thursday through Saturday by reservation only, so this isn’t a last minute dinner kind of place. However if you’ve been able to snag a spot here, you’ll be in for a treat! Located just outside of Woodstock in darling Pomfret, the drive to get to Cloudland Farm is absolutely gorgeous in the fall. The farm itself is the epitome of pastoral beauty, and the views from the veranda as you wait to be sat for dinner service are breathtaking. This is a bit of a fine dining experience, and it is a fixed 3 course menu that is expertly prepared by Cloudland’s chef.

Go Hiking at Marsh-Billings-Rockefeller Historical Park

When it comes to fall activities in Woodstock and throughout the state, hiking is always at the top of the list. The Marsh-Billings-Rockefeller Historical Park is home to over 20 miles of trails that wind their way through and around this beautiful protected space in Vermont. The forests are made up of a variety of trees that create the symphony of fall colors, including Sugar Maples, the tree most commonly responsible for that brilliant scarlet red you’ll find dotting the Vermont landscape in fall. The Pogue at Marsh-Billing-Rockefeller National Historical Park is an especially scenic place to walk on a fall afternoon, as the fall foliage surrounding this pretty pond makes for quite the picture in the autumn months. You can also access the South Peak on Mount Tom at this historical park, offering access to one of the best aerial views of Woodstock. Plus, one of the access roads for this particular hike is a part of an intricate historic carriage road system that was created back in the 1800s, so it’s an interesting area to explore.

Enjoy Queechee Gorge Village

Two quintessentially Vermont things can be found at the Queechee Gorge Village: cheese and antiques! With 17000 sq feet, the Vermont Antique Mall is one of the best in the US and is a definite must visit for any lover of collectibles, memorabilia, antiques, and more. Treasure hunting in this epic antique store is a great rainy day Woodstock activity. You can sample Cabot Cheese, feed alpacas, and pick up all kinds of Vermont souvenirs at this outdoor shopping center. Don’t forget to stop by the Queechee Gorge Bridge to take in those awesome views with the fall colors are ablaze.

Billings Farm and Museum

Billings Farm and Museum isn’t just a fully functioning working farm, it’s an outdoor history museum, too! This iconic Woodstock spot is open daily through October, then weekends only for the rest of the season, but there is an absolute plethora of fall activities to be found onsite, including touring the museum exhibits, visiting the farm animals, and strolling through the gardens (Oh, and the ice cream shop is open through October, too!). They host a variety of events throughout the year, including their annual Harvest Celebration, Family Halloween event, and Thanksgiving Weekend throughout the fall season.

Where to Stay During Fall in Woodstock, Vermont

The woodstock inn.

The  Woodstock Inn  has been a fixture in Vermont since 1793, starting out as The Richardson Tavern (which continues to serve as one of the Inn’s two restaurants serving up steaks and a to-die-for fondue). In 1830 it was expanded to become the Eagle Hotel, and today you’ll find eagles of all shapes and sizes throughout the property as a nod to it’s historic past. The original Woodstock Inn was built in 1892 becoming Vermont’s first winter sports destination. In 1967 the property was bought and renovated by Laurance Rockefeller (yes, of  that  Rockefeller family) and most recently a $16 million dollar renovation was completed in 2018. Today the overall feel of the Woodstock Inn is that of your most stylish friend’s country home – if that home came with an effusively nice staff, two world class restaurants, a luxurious 10,000 sq. foot spa, and activities to suite every taste and season.

Fat Sheep Farm

If you’re looking for a unique place to stay during your fall weekend visit, you’re going to want to check out Fat Sheep Farm . This working farm is so cute, and the property is extremely picturesque. We stayed in a modern cabin that was very comfy, with spectacular views of the Vermont countryside and the mountains in the distance. Our cabin had beautiful natural light, and after dark, the starry sky was breathtaking as we took in the night air on our porch. We participated in some of the farm chores like collecting eggs from the chickens and leading the sheep and goats from the barn to pasture. You don’t have to participate, but we wanted to get the full experience. We even tried our hand at milking the sheep! Added bonus: if you stay at Fat Sheep Farm, you’ll be just up the road from Harpoon Brewery, where you can enjoy a Harpoon Craft Cider, the perfect way to celebrate fall flavors… yum!

506 on the River Inn

Looking for an inn with gorgeous fall foliage views in Woodstock? We loved our stay at 506 on the River Inn , in part due to its peaceful location on the Ottaquechee River. The fall foliage views alongside the river can be enjoyed from your private riverside balcony, or while enjoying the firepit. There are complimentary s’mores each night from 7-9pm! Offering a boutique inn experience and generous amenities that include onsite dining, a heated indoor pool, sauna, and comfy cozy rustic yet modern Vermont vibes throughout. They also have an outdoor playground and indoor kids’ play rooms that are so nice to have if you’re traveling with the fam! We really appreciated the toddler play space. There are lots of fun fall things to do in Woodstock, Vermont. Hopefully this list of places to go and things to do will help you plan your fun fall trip to Woodstock!

If you like this post be sure to check out some of my other articles!

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The Very Best Things to do in Vermont in the Fall

When fall arrives, Vermont transforms into a kaleidoscope of vibrant colors. The Green Mountain State boasts some of the most stunning fall foliage displays in the entire country. The perfect time to visit Vermont ! This guide explores quintessential Vermont fall foliage activities. Get ready to explore the very best things to do in Vermont in the Fall !

Are You Ready to Explore the Best Things to Do in Vermont this Fall?

From crimson reds to sunny yellows, the landscape becomes saturated with jewel tones that dazzle the eyes. See places to visit in Vermont for a great fall vacation! Vermont in October is magical and memorable, to be sure. You will be delighted with the many fall foliage activities that visitors plan to travel on during fall foliage season.

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Fall Foliage Season in Vermont

From the top of the state in Beebe Plain to the bottom at Brattleboro, Vermont, you are sure to enjoy the best fall foliage in New England. It’s no wonder leaf peepers flock to  Vermont each autumn . After all, there’s no better place to immerse yourself in the spirit of the season. Whether you’re a foliage fanatic or simply looking for a quaint New England getaway, Vermont offers an abundance of activities and attractions perfect for fall. You will definitely find the best fall foliage in Vermont so find a place to stay and enjoy fall in Vermont!

So toss on your coziest sweater, grab a piping hot apple cider, and get ready to explore the very best ways to enjoy Vermont in the fall . This comprehensive guide covers everything from admiring Mother Nature’s canvases to devouring farm-fresh treats. Let’s dive in!

Exploring Vermont in the Autumn Season

The best time for peak foliage in the fall is generally mid-September through mid-October. Here’s a more detailed breakdown of the ideal times:

• Early September: Fall foliage starts to emerge in the northernmost parts of Vermont and higher elevations. If you want to catch the changing leaves early, visit places like Stowe and Jay Peak .
• Late September to Early October: This is peak foliage season in most of Vermont. The leaves are at their most vibrant and spectacular. Plan your trip during this window to witness the brilliance of autumn.
• Mid October: Southern and lower parts of Vermont reach peak color. The foliage here tends to lag behind the northern and mountainous regions by a couple weeks.
• Late October: Some lingering color remains, but many of the leaves have dropped. Still pleasant to visit, but not peak conditions. Best locations during this time are in southern Vermont.

Keep in mind that the foliage changes vary each year depending on weather and temperature. For exact reports, check Vermont’s official fall foliage website, as they issue weekly reports on the leaf peeping conditions around the state.

No matter when you visit in autumn, Vermont offers charming towns, scenic landscapes, and plenty of fall activities. Just aim for late September to early October if you want to see the most stunning fall colors at their prime. Check out following excursions – the best!

Crunching Leaves & Snapping Vermont Fall Pictures

While simply appreciating Vermont’s kaleidoscopic landscape can be a sensational experience, getting active outdoors amplifies the magic exponentially. As the locals say, “there ain’t nothing as fresh as clean, Vermont air”.

Lace up those hiking boots and hit the trails! Vermont’s hiking options are seemingly endless, but some can’t-miss routes include Mount Mansfield , Camel’s Hump, and the Long Trail . Wind through hardwood forests bursting with warm hues. Gasp in awe at panoramic vistas overlooking patchwork valleys. Breathe in the crisp, earthy air as you journey through the foliage .

Don’t forget to pack your camera! Capture snapshots of brilliant leaves dangling from branches, mirrored in glassy lakes, and carpeting the forest floor. For photography buffs, early morning and late afternoon light makes colors really pop.

Looking for more of the very best things to do in Vermont in the fall?

Prefer a more leisurely pace? Vermont’s scenic byways were made for lazy Sunday drives. Cruise along taking in gentle mountains cloaked in autumn’s finest. Snap photos at overlooks and quaint towns. Routes 100, 7, and the Green Mountain Byway offer spectacular scenery. Some of the following excursions – the best places to go!

Great Vermont corn mazes and hayrides along with many other Halloween events, haunted trails are a must! Make this part of Vermont must-see activities!

Planning to Visit Vermont? One of the best places to visit is Stowe

As mentioned previously, Stowe is easily one of the best locations to see the beautiful Vermont fall foliage . Autumn is the best time for an aerial perspective, hop on a chairlift ride! Dangling feet over dazzling hillsides topped with red and gold makes for an unforgettable experience.  Stowe is the perfect place to do this any time of the year. It's just part of what makes this part of Vermont so special. Stowe is also perfect for a hike during the Vermont fall season. Just don’t forget your coat and mittens!

If you're planning ahead for a ski vacation in the winter, a visit to the Vermont Ski and Snowboard Museum could perfectly complement your Vermont fall vacation. Stowe offers the best downtown shopping and dining, while you visit this corner of Vermont.

Autumn Delicious Delights – Munching On Vermont’s Autumnal Goodies

With an abundance of orchards, farms, and artisans, Vermont delivers endless options for scrumptious seasonal bites and sips. You'll find the best cider donuts, one of our favorite things, in Vermont!

Kick things off by picking your own bushel of crunchy apples—nothing screams fall quite like the experience of plucking ripe fruit straight from the tree. Follow the self-guided trail to the juiciest specimens, then relax under the branches with slices, cider, and an apple cinnamon donut. Divine!

Find the best apple orchards in Vermont to visit during peak fall:

• Scott Farm Orchard – Dummerston
• Chapin Orchard – Essex
• Hackett’s Orchard – South Hero
• Shelburne Orchards – Shelburne
• Adams Apple Orchard & Farm Market – Williston
• Allenholm Farm – South Hero
• Cold Creek Farm – Dummerston
• Sunrise Orchard – Cornwall
• Woodchuck Orchard – Brandon
• Booth’s Orchard – Westminster Station
• Burtt’s Apple Orchard – Cabot
• Alyson’s Orchard – Walden
• Sentinel Pine Orchard & Mapleworks – Shoreham
• Doe’s Leap Orchard – Bakersfield
• Happy Valley Orchard – East Middlebury
• Peck’s Orchard – Berlin
• Cedar Circle Farm & Education Center – East Thetford

Some fun activities at these orchards include picking your own apples, hayrides, corn mazes , farm animals, baked goods, and vegetable stands. They make for excellent fall family fun! Be sure to call ahead to check dates and hours.

Next, explore farmers markets bursting with harvest bounty. Chat with friendly growers and stock up on plump pumpkins, root vegetables, fresh cheese, maple syrup, and more. Bring home the flavors of Vermont to last all season long.

Farmer’s Markets You Will Simply Love to Visit

Here are some of the amazing things you can find at Vermont farmers markets and why you should make visiting them a priority:

• Locally Grown Produce – You’ll find the freshest, in-season fruits and veggies, straight from Vermont farms. Taste juicy heirloom tomatoes, crisp apples, and leafy greens at their flavorful peak.
• Artisanal Goodies – From jams and maple syrup to baked goods, cheese, and craft beverages, farmers markets are a treasure trove of local artisanal delights you won’t find elsewhere.
• Less Waste – By buying directly from the source, you skip packaging waste and miles traveled of big store produce. It’s better for the environment.
• Meet the Makers – Chat with talented farmers, bakers, and artisans. Hear their stories and support small businesses.
• Family Fun – Many farmers markets feature live music and activities for kids. It’s an enjoyable community experience for all.
• Seasonal Inspiration – Finding what’s fresh each visit sparks new recipe ideas and keeps your diet seasonal. Discover new-to-you vegetables too!
• Fresh Vermont Mountain Air – Wandering outdoor markets is an energizing break from crowded supermarkets.

Visiting farmers markets lets you connect with Vermont’s passionate producers while accessing the state’s very best harvest bounty. It’s a delicious win-win and just one of the many things to do in Vermont in the fall! Perhaps a fall foliage road trip is in order!

Speaking of maple, a visit to one of the many Vermont country stores is non-negotiable. Browse aisle after aisle of nostalgic candies, Vermont-made products, and whimsical Vermont crafts and creations. You’re bound to find the perfect souvenir, or five. Don’t leave without sampling their legendary maple creemees!

Best Places to See and Go in Vermont

And for an inside look at Vermont’s artisanal food scene, book a factory tour. Watch maple syrup being bottled, cheese wheels formed, ice cream churned, and teddy bears stitched. Then sample the goods, obviously! Local favorites include Ben & Jerry’s, Vermont Teddy Bear Company , and Cabot Creamery.

Vermont’s bounty of harvest happenings and flavors make fall an extraordinary time to plan a road trip. Just come to the State of Vermont hungry!

Appreciating Vermont’s Many Charming Villages in Autumn

In addition to natural splendor, Vermont is revered for its quaint villages bursting with rural New England charm. From Main Streets lined with colonial architecture to cozy cafes and boutiques, these towns invite you to slow down and savor simpler pleasures. There are many things to do in Woodstock as well as many other places to go. It's your best bet to enjoy a Vermont fall vacation you'll remember for years. Planning your Vermont fall foliage vacation starts here.

Visit Vermont in the Fall

Planning to visit? The best time to see fall in Vermont is September and October. For leaf peeping hubs, choices abound but consider  Stowe , Woodstock , Waitsfield, Manchester ,  Bennington and many other places in Vermont. Manchester is based in southern Vermont and has a special charm of it's very own. Each overflows with character and offers prime foliage viewing. Meander along sidewalks and duck into shops stocked with local art, crafts, woolens, and pantry staples like jams and  maple syrup . Visit a local Vermont corn maze and get lost, literally!

Don’t miss the opportunity to dine out and experience Vermont’s thriving farm-to-table restaurant scene. For dinner with a side of panoramic vistas, make reservations at one of Stowe or check out things to do Woodstock or discover Woodstock’s hilltop eateries. Try local specialties like cheddar ale soup, maple glazed salmon, or anything doused in Vermont maple . You can’t go wrong!

And while you’re exploring these darling hamlets, keep your eyes peeled for historic landmarks and cultural attractions. Vermont has no shortage of acclaimed museums—from the Shelburne Museum’s impressive Am ericana collections to Hildene’s glimpse into Abraham Lincoln’s family’s life. Fall is definitely the best time to visit Vermont! The largest city in Vermont is Burlington and you'll find many quintessential fall foliage activities around the Burlington Waterfront and Church Street. Grab a map of the best places to visit.

The quaint, unhurried pace of Vermont villages provides a delightful complement to the state’s vibrant, Vermont fall foliage. Meandering through their postcard-perfect streets is a top way to soak up Vermont’s old-fashioned essence.

Famous Vermont Ghost Stories and Haunting Tales

Here are some of the most famous ghost stories in Vermont with a title and simple description of each:

• Emily’s Bridge of Stowe  – The legend is probably the most famous Vermont “ghost story” of all. Supposedly, Emily fell in love with a man her family disapproved of. The two decided to elope and meet at the bridge at midnight. Emily arrived at the appointed time, but her lover never showed up. Distraught, she hanged herself from the bridge in despair. 
• Brattleboro Retreat  – The Brattleboro Retreat is a psychiatric hospital in Brattleboro, Vermont that has been around since 1834. It is said that the ghosts of former patients still haunt the halls.
• Deep Frozen Folks  – The story, reported to be true, tells of a poor, northern Vermont family who had established the idea of putting their elderly and weakest family members into cold storage until they could be thawed out just in time for Spring planting.
• The Hayden Family Curse  – From unexplainable illnesses to tragic accidents and unexplained deaths, some have speculated that the Hayden family was cursed and doomed.
• Champ: The Lake Champlain Sea Monster  – Champ is a legendary sea monster that is said to inhabit Lake Champlain on the border between Vermont and New York State.

• Alexander, William M. (Author)
• English (Publication Language)
• 74 Pages – 08/26/2018 (Publication Date) – Independently published (Publisher)

• Amazon Kindle Edition
• Lewis, Thea (Author)
• 129 Pages – 08/26/2014 (Publication Date) – The History Press (Publisher)

• Stansfield Jr., Charles A. (Author)
• 131 Pages – 06/11/2007 (Publication Date) – Stackpole Books (Publisher)

• 96 Pages – 09/25/2009 (Publication Date) – The History Press (Publisher)

• Used Book in Good Condition
• D'Agostino, Thomas (Author)
• 160 Pages – 05/28/2011 (Publication Date) – Schiffer Publishing (Publisher)

• Zwicker, Roxie J. (Author)
• 144 Pages – 09/25/2023 (Publication Date) – The History Press (Publisher)

• 160 Pages – 09/25/2023 (Publication Date) – The History Press (Publisher)

• Map reprinted on high quality bond paper

• Citro, Joseph A. (Author)
• 123 Pages – 03/22/2024 (Publication Date) – Independently published (Publisher)

• Ladley, Diane A. (Author)
• 160 Pages – 10/12/2009 (Publication Date) – Arcadia Publishing (Publisher)

Best Time to Visit During and Explore the Champlain Islands

Time to see fall foliage! For a quintessential Vermont fall getaway, head to the  Champlain Islands . This archipelago scattered across Lake Champlain delights visitors with stellar foliage views, cozy eateries, and small-town charm. Definitely one of the best places to see fall foliage!

Begin your journey in South Hero, an island oasis known for its apple orchards. Meander through the trees at Hackett’s Orchard, or Allenholm Farm, plucking ripe apples and selecting Vermont pumpkins as leaves drift down around you. Pumpkins can be found everywhere. One of the best things in the area are apples and pumpkins! Savor cider and donuts on the patio before stocking up on apples for the road.

Next, soak in brilliant views of the lake and New York’s Adirondack Mountains. Pull over at roadside farm stands and scenic outlooks to photograph vibrant autumn panoramas. Snap the iconic fall foliage photos with the changing trees and beautiful Lake Champlain as your backdrop.

Fall Colors in Vermont

Don’t miss the Island Line Rail Trail, an idyllic path connecting the islands over miles of Lake Champlain causeway to the town of Colchester. Walk or bike past shimmering blue waters, saturated in fall’s finest views and cool breezes.

When hunger strikes, cozy up at Victoria’s Café in South Hero . Savor Thai curries and noodles, juicy burgers, and their most popular dish, the Vermont Maple Duck, while planning your visit to nearby apple orchards.

Best Places to See Vermont Fall Foliage Season

With inviting inns and lodging, restaurants, and stunning natural beauty, the Champlain Islands deliver an idyllic fall escape. Meander through its small towns and uncrowded landscapes to experience Vermont’s harvest season at its finest.

Celebrating the Autumn Season with Things to do in the Fall

Beyond marveling at Mother Nature’s paintbrush and indulging in Vermont’s harvest, autumn here also signifies beloved traditions, festivals, and community.

Kick off your trip by attending a beloved Vermont fall festival—it’s a fabulous way to mingle with locals and imbibe the spirit of the season! Think live music, parades, food vendors, carnival rides, craft booths, and more. Top picks include several Vermont Apple Festivals, Manchester Fall Art and Craft Festival , Underhill Harvest Festival and VT Brewer’s Fest . Enjoy the best cider donuts you'll ever eat!

For family fun, visit a pick-your-own pumpkin patch or corn maze. Wander through towering stalks, play in piles of dried leaves, sip hot cider, and conquer the labyrinth. It’s an adventure sure to create lasting memories.

Looking for an authentic fall experience in Vermont? Head to the local cider mills and pumpkin patches! Immerse yourself in the harvest season, pick your own apples, and enjoy the vibrant colors of autumn. It’s a perfect way to feel like a true Vermonter!

Some of the best places to visit and top pumpkin patches and orchards in Vermont to visit in the fall:

• Adam’s Pumpkin Patch – Williston
• Peck’s Pumpkin Patch – Berlin
• Sam Mazza’s Farm Market – Colchester
• Victoria’s Cafe – South Hero
• Boch’s Apple Orchard – Swanton
• Morse Farm Maple Sugarworks – Montpelier
• Kingsbury Market Garden – Warren
• Mad Tom Orchard – East Dorset
• Nowland’s Tree Farm – Hartland
• Lewis Creek Farm – Starksboro
• Curtis’ BB’s Family Farm – Vergennes
• Dakin Farm – Ferrisburgh
• Hathaway Farm – Burlington
• Hall’s Pumpkin Patch – East Montpelier
• Rainbow Sweets Corn Maze – Pittsford
• Bean Road Farm – Colchester

Some activities at these patches include corn mazes, wagon rides, farm animals, and pumpkin picking. Call ahead for hours and be sure to bring the whole family for some old-fashioned autumn fun!

Or get your adrenaline pumping at one of Vermont’s popular fall races. Challenge yourself conquering the Green Mountain Marathon course, pedaling over Vermont’s peaks at the Vermont 50, or racing through autumnal forests on horseback at Green Mountain Horse Association’s Fall Finale .

See Fall in New England – See Fall Foliage in Vermont

However you choose to celebrate, foliage season in Vermont promises autumnal activities galore. Revel in the irresistible combination of stunning natural beauty and festive community spirit unique to the season.

Planning Your Vermont in Fall Foliage Getaway

As you prepare for your foliage foray in Vermont, keep these tips in mind to make your trip to Vermont so special:

• For peak colors, every year in the fall, visit from late September to mid October. The brilliance begins up north and descends south.
• Check Vermont’s foliage forecaster for updates on the changing leaves. Time your trip for vibrant vibrancy!
• Make reservations for lodging, restaurants, and attractions early. Fall is Vermont’s most popular season.
• Pack layers and rain gear. Early fall delivers fickle weather but the views are worth it!
• Fly into Burlington International Airport for the most foliage convenient access. Rent a car to properly explore.
• Grab a detailed Vermont roadmap. Meandering backroads lead to hidden gems!
• Follow Vermont tourism boards on social media for real-time foliage reports and inspiration.

The best places to stay in Vermont during the fall

With proper planning, your Vermont fall getaway will exceed all expectations! There is simply no shortage of things to do in Vermont in the fall.

Falling For Vermont’s Autumn Charm and Tasty Treats

As autumn descends on the Green Mountain State , a bewitching transformation occurs. Brilliant foliage, cozy villages, farm-fresh food, and festive spirit imbue Vermont with undeniable magic. It’s a season that delights the senses and satiates the soul.

So whether you seek stunning vistas, quaint main streets, apple orchards, or race courses, Vermont serves up the quintessential fall experience. Forget pumpkin spice lattes and hay bales—this is where you’ll find the authentic soul of autumn. A bountiful harvest of small cafes, restaurants, food stands, Maple creemees and all the autumn goodies that you can imagine. They’re all here in Vermont!

Some of the top restaurants in Vermont:

• Hen of the Wood – Burlington – Locally sourced new American cuisine in a rustic setting. Try the grilled trout or venison tartare.
• Prohibition Pig – Waterbury – Legendary BBQ joint serving up smoked meats, creative cocktails, and live music. Don’t miss the burnt ends.
• Simon Pearce – Quechee – Elegant fine dining with impressive views overlooking the waterfall. Known for their cheese plate.
• American Flatbread – Waitsfield – Cozy pizzeria with artisanal flatbread pizzas baked in a wood-fired oven. Great farm-to-table menu.
• The Farmhouse Tap & Grill – Burlington – Laidback gastropub with an extensive craft beer list and farm-inspired dishes like chicken and waffles.
• Bluebird Barbecue – Burlington – Southern BBQ flavors like brisket, ribs, and pulled pork in a hip, modern setting.
• Leunig’s Bistro – Burlington – Old-world French bistro serving classic dishes like cassoulet, trout amandine, and steak frites.
• Misery Loves Co. – Winooski – Comforting farm-to-table dishes made from local and seasonal ingredients. Don’t skip the bread pudding.
• The Essex – Essex Junction – Upscale continental dining with a vibrant bar scene. Try the duck two ways.

As the harvest sun sinks low in the sky and leaves drift earthward, embrace the crisp air, slower pace, and community camaraderie that defines our beautiful Green Mountain state. It’s a time of belonging, nostalgia, and memories that you’ll cherish long after departing.

So grab your flannel, hit the road, and come revel in the wonders, flavors, and fellowship that make autumn in Vermont so extraordinary. The Green Mountain State eagerly awaits your next fall visit!

Very Best Things to do in Vermont in the Fall

So whether you seek stunning vistas, quaint main streets, apple orchards, or race courses, Vermont serves up the quintessential fall experience. Forget pumpkin spice lattes and hay bales—this is where you'll find the authentic soul of autumn. A bountiful harvest of small cafes, restaurants, food stands, Maple creemees and all the autumn goodies that you can imagine. They're all here in Vermont!

A Local’s Guide To Foliage, Food, And Fun!

Are you ready to experience the breathtaking beauty? Get ready to immerse yourself in a stunning tapestry of vibrant colors and indulge in delicious local cuisine.

With its picturesque landscapes and perfect weather, Vermont is the ultimate destination for autumn enthusiasts like you. Did you know that October is the busiest month for visitors seeking the best foliage views? But don’t worry, we’ve got you covered with insider tips to help you navigate the crowds and make the most of your trip.

We’ll even provide you with travel tips, packing suggestions, and recommendations for the best lodging options.

So, get ready to embark on a memorable journey through Vermont’s fall wonderland and create cherished memories that will last a lifetime. We'll be ready to head for a Vermont ski area soon after the season so enjoy the fall foliage while it lasts!

Key Takeaways and a Few Dining Gems to Check Out!

• Vermont offers breathtaking beauty and vibrant colors in the fall.
• Charming towns like Stowe , Manchester , Woodstock and South Hero are certainly worth visiting.
• The Jericho Cafe and Tavern, Victoria’s Cafe and Rosie’s Restaurant in Middlebury are recommended eateries.
• Insider tips can help navigate crowds and packing appropriately for the fall weather is important.

Top Vermont Destinations in the Fall

If you’re planning a trip to Vermont in the fall, you’ll want to check out these top destinations. These include Manchester, Bennington, Waitsfield, Woodstock, and Stowe. Vermont is known for its stunning foliage, and these towns offer some of the best views. The Northeast Kingdom is also one of the best destinations for fall foliage colors and the traditional Vermont way of life.

For nature enthusiasts, there are plenty of hiking trails to explore. This provides an opportunity to immerse yourself in the vibrant autumn colors. If you prefer a more leisurely experience, take a scenic drive through the countryside. Witness the beauty of the changing leaves from the comfort of your car.

Each town has its own unique charm and attractions. These range from quaint shops and local art galleries to historic landmarks and cozy cafes. Make sure to visit these top destinations for an unforgettable fall experience in Vermont.

Art Galleries in Vermont

Here is a list of some of the top art galleries to check out in Vermont:

• Frog Hollow Vermont State Craft Center – Burlington – Features fine contemporary crafts by over 200 American artisans. Pottery, glasswork, jewelry and more.
• Amy E. Tarrant Gallery – Burlington – Represents contemporary Vermont artists. Paintings, prints, sculptures and crafts.
• The Front – Burlington – Avant-garde gallery exhibiting works by emerging and mid-career artists. Hosts openings and events.
• S.P.A.C.E. Gallery – Burlington – Artist-run gallery in the South End Arts District focused on contemporary art.
• Helen Day Art Center – Stowe – Exhibits work by national, regional and local artists. Offers art classes and events.
• Vermont Arts Council Gallery – Montpelier – Rotating exhibits highlighting Vermont artists. Craft, painting, mixed media and more.
• Art on Main – Manchester – Features primarily Vermont artists. Mixed media, paintings, pottery and photography.
• Northern Daughters – Vergennes – Small gallery owned by local female artisans selling jewelry, paper goods, textiles and more.
• Main Street Museum – White River Junction – Rotating contemporary art exhibits plus permanent folk art collection.
• Gallery at Equinox – Manchester – Represents contemporary artists from New England and Quebec. Painting, sculpture and photography.

Essential Vermont Autumn Travel Tips

To make the most of your trip, remember to pack appropriately for the weather in October and choose the right accommodation for your stay. Vermont’s fall weather can be pleasant, but it can also get cold, so it’s important to pack layers, including sweaters and jackets. Don’t forget to bring comfortable walking shoes for exploring the beautiful foliage.

As for accommodation, there are plenty of options to choose from in Vermont. Whether you prefer a cozy bed and breakfast, a charming inn, or a luxury resort, there’s something for everyone. Consider staying in popular towns like Manchester, Bennington, or Stowe, where you’ll have easy access to attractions and dining options. Just make sure to book your accommodation in advance, as October can be a busy time in Vermont.

Frequently Asked Questions

What are the best hiking trails to experience the fall foliage in vermont.

For the best photography spots and popular fall hikes, check out Camel’s Hump, Mount Mansfield, and the Long Trail. These trails offer stunning foliage views and are perfect for capturing the beauty of fall in Vermont.

Are there any festivals or events happening in Vermont during the fall season?

Yes, there are many fall festivals and harvest celebrations happening in Vermont! You’ll have the opportunity to immerse yourself in the local culture, enjoy live music, indulge in delicious food, and take part in fun activities.

What are some lesser-known towns or hidden gems to visit in Vermont during the fall?

For a truly authentic Vermont experience, explore the quaint villages and lakeside retreats hidden throughout the state. These lesser-known towns offer a sense of belonging and a chance to connect with the local culture in a more intimate setting. The Northeast Kingdom region offers spectacular scenic views and more of a laid-back, traditional Vermont experience.

Can you recommend any scenic drives or road trips to take in Vermont to enjoy the fall colors?

For fall foliage photography, embark on scenic drives like Route 100, Route 7, or the Green Mountain Byway. Smuggler’s Notch between Jeffersonville and Stowe is perhaps the most famous autumn drive of all. The best places to stay for fall foliage are Woodstock, Stowe, and Manchester. Enjoy capturing Vermont’s breathtaking colors!

So, now you have all the information you need to plan an amazing trip to experience fall in Vermont! From the stunning foliage to the delicious food, there’s something for everyone to enjoy. Don’t forget to pack your camera and layers of clothing to stay comfortable in the changing weather.

And here’s an interesting statistic for you: Vermont attracts over 3 million visitors each year during the fall season, making it one of the most popular destinations for foliage enthusiasts.

So start planning your trip and get ready to create unforgettable memories in beautiful Vermont!

Greensboro Vermont In The Northeast Kingdom

Experience Stowe Vermont Best Things to Do in the Fall

William Alexander

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• Frequently Asked Questions

Vermont comes alive in the wintertime, and even if you're not interested in skiing or snowboarding, this is the best time of year to appreciate the state's stark beauty, its warm comforts (like maple syrup), and its outdoorsy bent. For Vermonters, there is no such thing as bad weather, even though winter days can be bruisingly snowy, windy, and cold. It's an attitude you'll love embracing, even if you spend most of your vacation wrapped in a cocoon of plaid flannel. Of course, warming temperatures in the spring and summer alter but don't diminish the array of outdoor activities that make a visit to Vermont worthwhile, and fall is a stunning time to explore one of New England's best states for leaf-peeping.

Vermont has the longest ski season on the East Coast, which should tell you: It's cold and snowy here for practically half of the year. OK, that may be a bit of an exaggeration, but up in the mountains you can count on conditions allowing for snowmaking from about the middle of November through the middle of April. Killington Resort's latest closing day in recent history was June 1!

January is Vermont's coldest and snowiest month with temperatures rarely above freezing and often in the single digits Fahrenheit. Storms typically drop anywhere from a foot-and-a-half of snow at lower elevations to 40 inches or more atop the state's storied peaks.

Contrary to what some folks imagine, though, Vermont is not cold year-round. In the northern city of Burlington on Lake Champlain, the average high temperature is 68 degrees F during the day by May. Temperatures average a high of 81 degrees F in Burlington in July: Vermont's hottest month. Keep in mind that you'll always find cooler temperatures as you move up in elevation. Spring through fall, there's a good chance about one-third of the days in each month will receive some rain. 

If you're into the sort of rugged outdoor sports many Vermonters are—mountain biking, hiking, climbing, ATVing—you'll love that it never gets super hot and humid. Be mindful that while Vermont does not have a lake or the ocean to brew up foul weather, it still exhibits the sort of weather variability that is characteristic of the region. You'll want to be particularly prepared in the winter, when Vermont can get slammed by a Nor'easter. The state has also seen more than its share of woes during fall hurricane season, sustaining particularly heavy damage during 2012's Superstorm Sandy.

Because the great outdoors provides so many of Vermont's sought-after experiences, you won't find many "Closed" signs turning visitors away. Mother Nature largely decides what you can and cannot do. You can't snowmobile without snow, obviously, but you may be surprised to learn that Peace Pups will take you dogsledding (well, dog carting, actually), in the fall. Farms, another popular Vermont attraction, follow their own seasonal calendars with some, such as maple farms, active long before the first new plant life pokes above ground.

Ski resorts have also gotten in on the four-season act. After skiers and riders have put away their goggles and boots, head to Killington for gondola rides , Bromley for the alpine slide , or Jay Peak for the Pump House Indoor Waterpark . More traditional indoor attractions either operate on a year-round schedule or reopen in the late spring following a winter rest. The Vermont Attractions Association is a good resource when you're looking for things to do, as most members are open throughout the year.

In a state where powdery-white snow is measured in feet rather than inches, winter is peak season wherever there are peaks. Vermont is home to New England's largest and highest ski area ( Killington ), one of its chicest ( Stowe ), and more than a dozen more: all places to make winter memories even if you're not among those who can't resist carving your signature upon the glistening slopes. This is a season of sleigh rides and hot cocoa, of roaring fires (check out the one in the lobby of the Woodstock Inn & Resort ), of breathing in nature's cold, pure essence. Lodging rates are high, particularly on weekends and during holiday weeks, so try to get your runs in midweek if you're watching your budget.

Events to check out:

• Wassail Weekend , Woodstock: Enjoy sparkling light displays, heavily-decorated homes, and festive tunes through town during this weekend-long celebration.
• Stowe Winter Carnival , Stowe: This January festival has more than 40 season-appropriate events like ice carving, ski movies, and snow golf tournaments.

Spring is Vermont's least predictable season, and locals label this period when winter begins to relinquish its hold, "mud season." Don't stay away, though. Not only does Vermont offer New England's best late-season skiing, but it also produces more maple syrup come springtime than any other U.S. state. To find a sugar shack, take a leisurely drive through practically any small town and watch for hardwood smoke billowing from the chimney of a small outbuilding. Chances are good there's an evaporator inside turning sap into liquid gold for your pancakes. If you don't want to leave your syrup mission to chance, consult the Vermont Maple Sugar Makers' Association's member listings . As snow melts into streams and the ground starts to solidify, join the anglers who know Vermont's rivers, like the Battenkill, are among New England's best places to fly fish.

• Vermont Maple Festival , St. Albans: Enjoy all things syrup during April with this festival dedicated to the sticky stuff. There are parades, specialty food stalls, live music, and more.

Those who know Vermont primarily as a winter destination are often surprised to find summer delivers polar opposite weather. Days are long and may be warmer than you anticipate, particularly as you ascend into elevations where the air is thin and the sun beats down on exposed mountain faces—sunscreen is a must. And cold Vermont craft beers will tempt your thirst. This is a season of lake swims, boat rides, farmers' market visits, gentle walks with your dog, and outdoor farm-to-table dining . It's also a high-energy time of year to kayak the boulder-strewn rapids and drops of the Wells River, to ride the mountain coasters at Killington and Okemo, to fly high on a Stowe Ziptour Adventure , to bike Kingdom Trails , and to give paragliding a go at Morningside Flight Park .

• Discover Jazz Festival , Burlington: Jazz musicians from Vermont and the surrounding area flock to Burlington for a week of stellar music.
• Quechee Hot Air Balloon Festival , Quechee: Settle in to watch more than 20 hot air balloons take to the skies. There's also live music and plenty of food on offer.
• Vermont Quilt Festival , Essex: More than 6,000 people arrive in Essex during June to celebrate all things quilting. Visitors can learn about traditional and modern techniques while exploring exhibitions and meeting quilters.
• Vermont Brewers Festival , Burlington: Vermont has world-class beer and this festival will show you why with different styles and dozens of brews on tap.

If you're averse to winter's chill, fall in Vermont will be the season that captures your heart. From late September through the first three weeks of October, starting up near the Canadian border and in the highest elevations, then progressing south, Mother Nature works her autumn magic. Swamp maples flame crimson; the poplars that cling to high rocky outcrops shimmer gold; and, by the dawn of October, every deciduous tree has donned shades of red, yellow, and orange. Drive scenic country lanes or even well-traveled Route 100, and you'll be tempted to pull over often to snap glorious photos, to pop into antique shops and the beloved Vermont Country Store , and to experience the countryside Robert Frost described in many a Vermont-inspired poem. Make a scavenger hunt to find the state's 100-plus covered bridges, its prettiest churches, its barns and silos, and so many cows…all tucked into this vivid landscape.

• Southern Vermont Garlic and Herb Festival , Bennington: With humble beginnings, this festival hosts more than 200 vendors and offers tons of live music, food trucks, and more to 16,000 guests over the course of two days.
• Vermont Pumpkin Chuckin' Festival , Stowe: Tossing pumpkins in a trebuchet may sound niche, but this festival has been going strong since 2008.
• Vermont Sheep & Wool Festival , Tunbridge: This festival is the perfect time to stock up on high-quality, ethically-produced wool textiles and yarn.

Winter is the best time to plan a trip to Vermont, not just for the snow sports but also to enjoy the coziness and warmth of this outdoorsy state.

Every year is different, but fall foliage in Vermont typically peaks at some point between late September and mid-October.

Vermont has the longest ski season on the East Coast, lasting from mid-November to mid-April.

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10 Of The Most Unique Places To Visit In Vermont

• Visit the Ben & Jerry's Flavor Graveyard and pay homage to retired ice cream flavors like Makin' Whoopee Pie and Economic Crunch. Best time to visit is in the summer for a factory tour and ice cream tasting.
• Explore the Museum of Everyday Life in Glover and indulge in nostalgia by viewing exhibits of vintage detergent boxes and toothpaste tubes. Best time to visit is on weekends for special exhibits.
• Experience the unique tradition of the Woodstock Town Crier in Vermont's most idyllic fall town. Witness the daily bell ringing at 5:55 pm in the summer and enjoy the old-time charm of Woodstock.

The New England state of Vermont is known for its quaint small towns for weekend trips , rolling green mountains, maple syrup, and some of the best fall foliage in the US. But beyond the quintessential Vermont imagery lie some incredibly unique and unexpected sights.

From a graveyard where retired Ben & Jerry's ice cream flavors are laid to rest to a museum dedicated to the mundane objects of everyday life, Vermont offers many off-the-beaten-path attractions that most tourists never discover.

Forget busy Burlington and mainstream Stowe. To experience the truly singular side of the Green Mountain State, add the following most unique places in Vermont to visit to the vacation itinerary and discover some of the many hidden gems on the East Coast.

Ben & Jerry's Flavor Graveyard

At the Ben & Jerry's factory in Waterbury, Vermont, devoted ice cream lovers can pay homage to flavors of the past in the Flavor Graveyard. Retired ice cream varieties like Makin' Whoopee Pie, Dastardly Mash, and Economic Crunch lie "dead and buried" under wittily written gravestones.

The tongue-in-cheek memorial is next to the Ben & Jerry's production plant where travelers can take a factory tour and sample today's popular flavors. It's easily one of the most unique attractions in Vermont!

• Landmarks: Gravestones for retired ice cream flavors like Makin' Whoopee Pie and Economic Crunch
• Best Time to Visit: Summer, when people can take a factory tour and enjoy an ice cream after
• Things to Do: Take a factory tour, sample new ice cream flavors, visit the Flavor Graveyard

Related: What Is A Creemee? Here's What To Know About The Vermont-Only Ice Cream

The Museum Of Everyday Life

For a truly singular experience in one of the most unique museums in Vermont, head to the tiny town of Glover and visit the Museum of Everyday Life. This quirky collection contains over 7,000 items that capture the mundane objects of American life in the 20th century.

Exhibits like vintage detergent boxes, old toothpaste tubes, and 1970s Tupperware aim to provoke nostalgia and observations about consumerism and culture. This overlooked museum offers an amusing look at everyday artifacts many take for granted.

• Landmarks: Collection of over 7,000 mundane 20th-century objects
• Best Time to Visit: Weekends when they have special exhibits
• Top Attractions : Vintage detergent boxes and toothpaste tubes that provide a nostalgic look at everyday artifacts

Woodstock Town Crier

Vermont's most idyllic fall town, Woodstock , has an unusual daily ritual: the sounding of the Town Crier Bell. Every day in the summer at 5:55 pm, Woodstock's official Town Crier appears on the Village Green wearing a colonial costume and rings a large bell while reciting a traditional proclamation.

The tradition dates back over 100 years and continues to delight visitors who gather to witness this iconic Vermont custom. Travelers staying overnight in Woodstock can experience a bit of old-time Vermont charm at this brief but lively event.

• Landmarks: Costumed Town Crier, large bell
• Best Time to Visit: Summer at 5:55 pm for the daily bell ringing
• Things to Do: Watch the Town Crier's recital, explore Woodstock, stay overnight to catch the event

Related: Visit Woodstock, New York & Do These 10 Awesome Things

The Old Round Church In Richmond

Built in 1812, the Old Round Church in Richmond, Vermont, is a rare example of 16-sided architecture. The circular design was chosen for its acoustic properties as well as symbolic meaning. Visitors enter through an imposing wooden vestibule into a soaring open sanctuary. The church interior has original box pews, a wine-glass style pulpit, and a wooden balcony.

Guided tours provide a close look at the fascinating architecture and history of this unique Vermont church. The adjacent cemetery contains gravestones dating back to the Revolutionary War.

• Landmarks: Circular 16-sided church, historic box pews and pulpits
• Tour Duration: 30-45 minutes for a guided tour
• Top Attractions : Architectural design, original antique interiors, adjacent Revolutionary War cemetery

The American Precision Museum

The American Precision Museum in Windsor celebrates an invention that revolutionized manufacturing in the early 1800s. At the nearby former Robbins & Lawrence factory, inventor Thomas Blanchard created one of America's first modern assembly lines and mass-produced interchangeable, identical parts using large machines.

Travelers can explore seven floors of exhibits on New England's first mechanized factory, examine antique machine tools, and gain an appreciation for how this technology fueled the Industrial Revolution. Interactive displays let visitors see demonstrations of the historic manufacturing process.

• Landmarks: Antique machine tools and old factory equipment
• Things to Do: Explore 7 floors of interactive exhibits on manufacturing history
• Top Attractions: See demos of antique machines and learn about America's first assembly line

Knight's Spider Web Farm

Crawling with creativity, the Spider Web Farm in Williamstown, Vermont, is home to the world's largest spider web collection. Artist Dona Dunn has been collecting, cataloging, and curating spiderwebs for over 20 years. Her nature-inspired folk art gallery displays over 5,000 different spider web types sourced from all over the world.

Visitors can take self-guided or private tours through rows of eclectic barns housing this extensive arachnid archive. For those seeking quirky roadside attractions in Vermont, this place spins an unforgettable web.

• Landmarks: Collection of over 5,000 different spider webs
• Length/Distance: 1-mile self-guided tour through barns
• Top Attractions: Observe the diversity of spider webs, browse the quirky folk art gallery

Bellows Falls Petroglyphs

Although Vermont is not ranked among the best places to see petroglyphs in America , the state does have some spots to see these ancient sketches. Etched into the rocky banks of the Connecticut River are ancient rock carvings theorized to be Native American petroglyphs. The carvings depict faces, figures, footprints, and symbols.

They were rediscovered in the 1920s near Bellows Falls, although their precise origins remain unknown. A steep climb down the cliff face via metal staircases and ladders provides access to view the petroglyphs up close.

This fascinating archeological site in Vermont offers a glimpse into the state's indigenous roots and is believed to be the largest collection of Native rock carvings in the state.

• Landmarks : Ancient rock carvings depicting faces, figures, and symbols
• Difficulty Level: Moderate hike down steep cliff via ladders and staircases
• Top Attractions: View Native American rock carvings, explore Vermont's indigenous history

Related: America's Oldest Petroglyphs Are 3x Older Than The Pyramids

The Forgotten Village Of Greenbanks Hollow

Nestled deep in the remote Green Mountains lies the abandoned village of Greenbank's Hollow. In the 1930s, the government purchased and evacuated residences in the area to establish Greenbank's Hollow as watershed land. The once-vibrant logging village became one of the ghost towns in Vermont, seemingly frozen in time, with empty homes, shops, and railroad infrastructure slowly being reclaimed by nature.

Adventurous hikers can explore this eerie lost village, complete with rusty equipment, moss-covered buildings, and glimpses into the region's lumber history. The Wampahoofus Trail is also a great option for those hunting the region’s mythical creature . There are several glamping spots in the Green Mountains for those planning to stay for a few days.

• Landmarks : Abandoned 1930s logging village, empty homes and buildings
• Length/Distance: 2 miles round trip hike into a remote village
• Top Attractions: Explore eerie abandoned town frozen in time, glimpse logging history

The Bread And Puppet Museum

Glover, Vermont, is also home to the Bread and Puppet Museum , housed in a red brick building containing decades of theatrical performances. The politically radical puppet troupe Bread and Puppet Theater was founded in the 1960s and is best known for its larger-than-life papier-mâché puppets.

The museum's exhibits feature instruments from past anti-war parades, circuses, and pageants, along with posters and videos documenting the group's productions. Travelers can watch Bread and Puppet rehearsals and tour workshops where the magic happens.

• Landmarks: Collection of giant paper-mâché puppets from political theater performances
• Tour Duration : 1-hour self-guided tour
• Things to Do: View puppets, watch rehearsals, time puppet-making workshops

Junk Locomotive

In the self-proclaimed "Best Lil' Town in Vermont'' lies a whimsical roadside attraction. The town of Chester erected a full-sized locomotive sculpture completely made from scraped metal and junk parts. Constructed by local resident Tom Boisvert, this quirky junk locomotive delights visitors who stop by the picturesque Stone Village Museum.

The recycled train engine symbolizes Chester's railroading history and demonstrates Vermont's strong folk art heritage - proving that creativity and community can transform piles of junk into an unforgettable work of art.

• Landmarks: Full-sized train sculpture made from recycled scrap metal
• Best Time to Visit: Summer, when you can browse the outdoor Stone Village Museum
• Top Attractions: Whimsical recycled folk art sculpture represents Chester's railroad history

• 7 Of The Most Charming Small Towns To Visit In New England

Tucked away in the northeastern corner of the United States , New England is famous for being one of the country's most beautiful and charming regions. Named by English explorer Captain John Smith in 1614, it is unsurprising that so much of the area's charm comes from its rich history, evident in its quaint small towns. From state to state, each of these towns has its own distinct past, paired with an abundance of natural beauty, from maritime shores to majestic mountains and everything in between. Whether visiting a coastal town with stunning beaches and a fascinating shipwreck museum or a town with Vermont’s highest waterfall and a mountain path used by smugglers long ago, no two attractions are exactly the same, but each will delight visitors in their own way.

Provincetown, Massachusetts

For over 400 years, the free-spirited coastal town of Provincetown , Massachusetts, has stood as a symbol of acceptance. As far back as 1620, the Pilgrims arrived here on the Mayflower in search of religious freedom. It was in Provincetown, at the northern tip of Cape Cod, that they found solace in the region's scenic shores. Throughout the centuries, the town has continued to champion freedom, and today, it embraces visitors and residents of all faiths, ethnicities, and sexualities, making it especially popular with LGBTQ vacationers.

Upon arrival to Provincetown, you will find that the kind locals are just one of the many welcoming features. From sand to sea, natural beauty will enchant and welcome you at every turn. Bike rides are a popular way to see the town, especially along the 5.25-mile Province Lands Bike Trail, which guides you through Provincetown's famed dune system. Not too far from the trail, Arnold’s Bike Shop is a great place to snag a rental if you left yours at home. If you would prefer a hike instead, the Beech Forest Trail is a gorgeous 1-mile loop through a beech tree forest, shading strollers from the sun.

For those craving sunshine, Race Point Beach is the perfect shore to soak up some rays and enjoy the golden sand and bright blue waters, while Herring Cove has calmer waves great for families. For a break from the outdoors, Commercial Street is a fun follow-up, with 3 miles worth of adorable shops, restaurants, and attractions. Stop in at Shop Therapy for a trip memento, The Canteen for classic seafood bites, and the Provincetown Museum of Art to explore its exhibits.

Nantucket, Massachusetts

Nantucket , a secluded island town in Massachusetts, may require some effort to reach, but the journey is well worth it. Spring and summer draw the most visitors, enticed by this beach town's warm weather and sunshine. But what sets Nantucket apart from other resort destinations is that most of its 80+ miles of beachfront are open to the public, except for the Cliffside Beach Club. Families with young children often choose Children’s Beach for its playground and calm waters, while Brant Point reigns as the most popular shore, renowned for its soft sand, boat watching, and views of the iconic Brant Point Lighthouse.

For those seeking an adventure on Nantucket Harbor, boat agencies like Nantucket By Water offer a variety of unique tours, including Cocktail and Sunset cruises, as well as a Sip and Fish tour where kids can learn to cast a line while adults relax and sample refreshing beverages. Alternatively, land lovers can explore the town's indoor maritime attractions. The Nantucket Whaling Museum is a beloved local spot, and the Egan Maritime’s Nantucket Shipwreck and Lifesaving Museum is also a must visit. Shortly after, in June, the Maria Mitchell Association and Loines Observatory will also reopen, offering the whole family a fun and enriching experience. Visitors can tour the Natural Science Museum, interact with a hands-on aquarium, and even gaze at the stars through the Loines Observatory research telescope.

Bristol, Rhode Island

Named after a riverside city in England , Bristol, Rhode Island, has a rich maritime history much like its namesake. To set the scene for your stay, the Herreshoff Marine Museum is a must-visit and a great first stop. The museum features a fascinating look into the area’s maritime and boating history. But for a firsthand experience of the beauty of Narragansett Bay, head to Colt State Park. Here, visitors can enjoy 4 miles of paved paths along the bay, perfect for biking (bike rentals are available at Bristol Bikes on Thames St) or strolling. This idyllic park also features numerous picnic pavilions, a fishing pier, and a canoe/kayak launch, providing ample opportunities to soak in the splendor of the bay all day long.

Next to the park, the Bristol Town Beach is a charming shore. Adjacent to this, the Coggeshall Farm Museum brings 1799 Bristol to life with its living museum depicting pastoral farm life. If you are interested in history and nature, other nearby attractions include Mount Hope Farm, another living history museum dating back to the 1680s, as well as the Blithewold Mansion, Gardens & Arboretum. The 33-acre estate offers tours of the historic mansion and its breathtaking gardens, complete with rare plants and intricate stonework, making it a showstopper in the spring and summertime, so make sure to have your camera ready. In addition, if you happen to visit Bristol in the summertime, their 4th of July parade is legendary. Founded in 1785, the Bristol Fourth of July Parade is the oldest Independence Day celebration in the country.

Westerly, Rhode Island

If you like the sound of a town blending history and nature, look no further than charming Westerly . A little over an hour’s drive from Bristol, this Rhode Island beauty was founded by English colonists all the way back in 1661 and has diligently preserved its rich history over the centuries. The Babcock-Smith House Museum is one example, showcasing a gorgeous Georgian mansion dating back to 1734. As time marched on, the Granite Theatre emerged in 1849, built in the elegant Greek Revival Style. Today, it continues to host a diverse array of performances, from Broadway plays to cabaret.

Venturing into the great outdoors of Westerly, you will find an abundance of natural beauty. Misquamicut State Beach beckons with a half-mile stretch of sandy shore, perfect for families, complete with a playground and gazebos for those seeking respite in the shade. For a more nature-focused outdoor experience, the Napatree Point Beach & Conservation Area also offers a pretty shoreline. However, as a designated “Globally Important Bird Area,” this beach is more of a haven for appreciating nature. So, if you are yearning for that quintessential Rhode Island pier atmosphere, Atlantic Beach Park is your ideal destination. A local landmark since 1921, this boardwalk park is the epitome of classic beachside enjoyment, whether you are indulging in patio dining at the Windjammer Surf Bar, lounging by the beach, or taking a whirl on the park’s star attraction, a Herschell-Spillman Carousel built in 1915.

Woodstock, Vermont

Journeying to "The Green Mountain State," Woodstock is a Vermont village that will capture your heart from the moment you arrive. As a hub for artisans, craftsmen, and entrepreneurs in the 1700’s, Woodstock maintains this legacy to this day. Spring and summer are the prime seasons to experience the vibrant artisan culture, with events like the Made with Pride Arts and Crafts Fair, and the farmers and craft market every Wednesday starting in May at Market on the Green. Year-round craft galleries such as Collective-the Art of Craft feature a diverse range of artisans, from glassblowers and ceramicists to woodworkers and jewelry makers.

Beyond its thriving artisan scene, Woodstock offers an enchanting outdoor experience and an opportunity to delve into the area's history. In mid-to-late August, the Billings Farm & Museum transforms into the largest sunflower house in the United States, with its 20,000 square-foot farm adorned with a breathtaking array of yellow, red, and orange sunflowers. Summertime also beckons visitors to Vermont's only national park, the Marsh-Billings-Rockefeller National Historical Park. Here, you can explore the historic Victorian mansion, enjoy a picnic in the gardens, and traverse over 20 miles of trails through the surrounding forests, taking in the rolling hills and scenic overlooks.

Stowe, Vermont

Located around 73 miles north of Woodstock, in the foothills of Mount Mansfield, lies the charming town of Stowe . While you may know Stowe for its ski slopes, spring and summer are equally vibrant times to visit this mountain town. Begin your visit in walkable downtown Stowe, where nearly 50 shops, restaurants, and galleries are housed in charming 19th-century buildings. Notable establishments include the Stowe Mercantile souvenir store, Whip Bar and Grill, and the Bryan Fine Art Gallery, to name a few.

For those seeking outdoor fun and a one-of-a-kind view, the Moss Glen Falls hike is only a 5-minute drive from the historic downtown. The waterfall itself is a mere quarter-mile trek from the trailhead and stands at an impressive 85 feet in height, making it the tallest and most beautiful cascade in all of Vermont. Outdoor enthusiasts can also relish in the beauty of Smugglers Notch State Park, known for its narrow pass through the Green Mountains, which was once used as a smuggling route to Canada and, later, an escape route for enslaved people. Visitors can explore the scenic pathway lined with 1,000-foot cliffs and enjoy anything from hiking, rock climbing, cave exploring, and more.

Camden, Maine

Like other charming New England towns, Camden , Maine, is renowned for its vibrant summer scene. Positioned on the shores of Penobscot Bay, an inlet of the Gulf of Maine , it attracts ocean enthusiasts eager to bask in the splendor of the Atlantic . Camden Harbor Cruises offers an invigorating aquatic adventure, while Laite Memorial Beach beckons with its picturesque grassy park and pebbled shore, perfect for beachcombing and boat watching. During the summer, Camden also hosts two annual sailing celebrations: the Maine Windjammer Festival and the Parade of Sail.

For those who prefer to remain on solid ground, Camden offers a plethora of land-based experiences as well. The town's historic district boasts an array of 19th-century homes and the restored 1893 Camden Opera House, a delightful venue for a show. You can also visit Camden Hills State Park to savor harbor views from land. With 30 miles of hiking trails, many opt to witness a breathtaking sunset over the bay after trekking to the summit of Mount Battie. And for those seeking stunning views without the hike, a scenic drive up the mountain on Auto Road offers sweeping panoramic views of the bay and its islands.

Final Thoughts

With a name like “New England,” it is impossible not to compare the region to that of the British country. And while the area certainly shares certain historic and cultural ties, it ultimately stands apart as its own entity, famous for paving the way for the United States. Whether visiting Provincetown, Massachusetts, where the Pilgrims first stepped onto North American soil in search of freedom, or Stowe, Vermont, where a mountain path paved the way to autonomy and independence for smugglers and enslaved people, New England’s wealth of history and natural splendor will enchant all who visit.

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Where are the cicadas? Use this interactive map to find Brood XIX, Brood XIII in 2024

In a few weeks, over a dozen states will be abuzz as trillions of periodical cicadas will emerge from their yearslong underground stay.

Broods XIX and XIII will emerge in a combined 17 states, mostly in the Midwest and Southeast, in a rare, double brood event . These two broods last emerged together 221 years ago, and after this year are not predicted to do so again until 2245.

Once conditions are right, the two broods will emerge in massive numbers to feed, make noise, mate and die. Here's what to know about where to find the 13-year Brood XIX and the 17-year Brood XIII.

2024 double cicada broods: Check out where Broods XIII, XIX will emerge

The two cicada broods will emerge in a combined 17 states across the Southeast and Midwest, with an overlap in parts of Illinois and Iowa. They will emerge once soil eight inches underground reaches 64 degrees, expected to begin in mid-May and lasting through late June.

The two broods last emerged together in 1803 , when Thomas Jefferson was president.

What is a periodical cicada?

Both the 13-year Brood XIX and the 17-year Brood XIII are periodical cicadas, which emerge every 13 or 17 years across North America. They differ from annual cicadas, which emerge every year.

You may remember the last periodical brood to emerge in huge numbers: the 17-year Brood X that was found in 2021 throughout the Midwest and Eastern Seaboard.

Annual cicadas, which are dark green to black with green wing veins, are  typically larger than periodical cicadas , which are recognizable for their red eyes, red legs and red wing veins, according to North Carolina State University Extension.

Periodical cicadas emerge earlier, usually in mid-to-late May as opposed to annual cicadas in July and August. According to North Carolina State University Extension, annual cicadas begin mating, " singing conspicuously " and lying eggs about two weeks after they emerge. Their first nymphs will fall to the ground and begin feeding on roots under the soil, and fully-developed nymphs will emerge two years later and molt into adults.

Above ground, periodical cicadas have a similar life cycle, appear in much larger numbers and are much louder. At the end of their season, the next generation of nymphs move underground and remain for either 13 or 17 years.