Heading to Sleepy Hollow for Halloween? Here's what to see and do

sleepy hollow halloween tour

Come October, this Westchester village along with its neighbor Tarrytown, becomes Halloween central, based around its long history and as the setting for Washington Irving's famed "Legend of Sleepy Hollow," the tale of the hapless school teacher Ichabod Crane and his nemesis the Headless Horseman. There are myriad things to do in both villages, from walking tours of its historic Sleepy Hollow Cemetery and Old Dutch Churchyard, to ghost tours of the historic Music Hall in Tarrytown to experiencing a Gothic mansion after dark!

While you're there, check out historic sites such as Kykuit, the Rockefeller estate and Philipsburg Manor, a historic 17th century farm and gristmill located across the street from Sleepy Hollow cemetery. Go to historichudson.org for more info on these sites.

There's enough listed here to keep you busy for an entire weekend, but be aware, some dates sell out quickly, so check websites for availability:

Glass Pumpkin Patch, Oct. 14-16

For the first time, visitors can walk through a maze of hay bales featuring special hand-blown glass pumpkins displayed at Kingsland Point Park. Proceeds from the sale of the glass pumpkins benefit the Make-A-Wish Hudson Valley Chapter. Food trucks will be available. The event is free to the public, although a parking fee will apply. 10 a.m.-5 p.m. Oct. 14 - 16. Kingsland Point Park. Visit glasspumpkinpatchfundraiser.com for more information.

More scares: Halloween haunt opens in vacant Yorktown department store

Dining: Old-school Italian restaurant opens in Peekskill

Fall fun: Grab your bike for 11 easy rides in the Hudson Valley

'The Legend,' thru Oct. 16

Audiences will be treated to a cirque/theatre noir production of Washington Irving's "The Legend of Sleepy Hollow," with narration by Washington Irving himself – in hologram form, commemorating the 200-year anniversary of Irving's spooky tale of Ichabod Crane and the Headless Horseman. Tickets are on sale now at SleepyHollowLegend.com. The show will run through Oct. 16 in the “Legend” Circus Tent on the East Parcel at 60 Continental Street in Sleepy Hollow. Showtimes: Fridays, 7 p.m.; Saturday, 2 and 7 p.m., and Sundays, 2 and 7:30 p.m. Shows run for an hour and a half and include an intermission. Tickets are $30 online and $40 at the door. Recommended for ages 10 years old and up. For more information, contact Westchester Circus Arts at 914-275-5711.

'Hulda, The Other Legend of Sleepy Hollow,' Oct. 15,-16, 22-23, 29-30

Once shunned as a witch, Hulda of Bohemia is now remembered as an 18th-century patriot and healer. This one-woman story telling experience was written by Carla Lynne Hall and Jim Keyes and is performed by Hall with original music performed by Keyes. Performances are held at 1 p.m. and 3:15 p.m. at the Old Dutch Church of Sleepy Hollow, Oct. 15-16, 22-23, 29-30. Tickets are $25 adults; $20 children. The Old Dutch Church is located at 430 Broadway, Sleepy Hollow. Find tickets at tickets.hudsonvalley.org/events

Sleepy Hollow Haunted Hayride & Block Party, Oct. 21,22

The Haunted Hayride legend rides again into the dark night where ghosts and goblins loom. The block party begins at 5 p.m., however, the hayrides have already sold out. Dates: Oct. 21, 22. Block party begins at 5 p.m. For more info, go to sleepyhollowny.gov. No fee for the block party on Beekman Avenue that features food for purchase, music and bouncy castles. 

Hulda's Night, Rockefeller Preserve, Oct. 21,22

Hulda’s Night is an adventure into the history and legends of the Rockefeller State Park Preserve through live performance. As guests hike through the dark woods with lanterns guiding the way, they will encounter various people, from The Storyteller, who recounts legends by fireside to the “witch” herself. Hulda, lonely and gravely misunderstood, awaits to tell you her side of the story. Tickets are $30. For more information, visit:  friendsrock.org

Tarrytown Halloween Parade, Oct. 29

Expect floats, costumed revelers, and bands along Broadway and then down Main Street to a the reviewing stand where prizes will be awarded. Begins at 5:30 p.m. Rain date is Oct. 30. Go to  tarrytownhalloweenparade.com

Sleepy Hollow Cemetery Tours, thru November

This historic cemetery is the final resting place for author Washington Irving, who wrote "The Legend of Sleepy Hollow," as well as the historic 17th century Old Dutch Church. There are several events planned around Halloween, from cocktails with the dead, to a murder mystery, along with daytime and evening walking tours, some led by lantern light. Events take place in September, October and select dates in November. For the complete schedule, a link to purchase tickers and more information, go to  sleepyhollowcemetery.org/walking-tours  or call 914-631-0081. Events, tours begin at Sleepy Hollow Cemetery North Gate, 540 North Broadway. 

'The New York Grimpendium,' Oct. 28

A special treat for Halloween, Lyndhurst welcomes author J.W. Ocker who will give a special talk on all things grim in our region! Based on his bestselling book, "The New York Grimpendium," Ocker will regale visitors with a personalized itinerary of the best grim and spooky sights nearby, including Lyndhurst itself! Talks at 2:30 and 5:30 p.m. Tickets are $30. For tickets, more info go to lyndhurst.org/events. Lyndhurst is located at 635 S. Broadway, Tarrytown.

Ghost Tours of The Music Hall, thru November

If you've been to a performance or show at this historic theater, this is a fun event to experience all its glories and its past! Storyteller Jonathan Kruk leads the 45-minute tour of the historic theater, built in 1885, and home to events as wide ranging as President's speeches to women suffrage rallies; roller skating to movie screenings of "Gone With The Wind." It is a vessel through which many people pass. And some don’t leave 
 The building is an official site of the Haunted History Trail of New York.  Gotham Paranormal Research Society  has investigated the Music Hall several times and has consistently detected paranormal activity including intriguing EVP (electronic voice phenomena) audio files and EMF (electromagnetic field) readings. Tours may be led by Chant Macleod. 13 Main St., Tarrytown. For dates and ticket reservations, sold online only, not at the box office, go to https://tickets.tarrytownmusichall.org.

Lyndhurst After Dark, Oct. 21-23, 29-30

Tour the mansion once home to Gilded Age financier Jay Gould by candlelight, see rarely viewed special collection pieces on display surrounded by festive Autumnal decor.  Performers will relate in-depth stories regarding  Victorian mourning practices, customs, and spiritualism, a popular social pastime of the era. All visitors must have a pre-purchased ticket for this performance. A limited number of tickets are available and time slots do sell out. For tickets and more info go to lyndhurst.org . 635 South Broadway, Tarrytown

SUP Witches Festival at Horan's Landing, Oct. 16

If you are searching for a wicked sight, come to Horan's Landing for the 3rd Annual SUP Witch Paddle. Witches will gather and "The Legend of Sleepy Hollow," will be told. Join the witches on the water or stroll along the riverwalk. Vendors, food, brews and spooky views are available. Costumes encouraged! All paddlers must register in advance to participate at rivertownssupyoga.com. Noon - 4 p.m. (Rain date October 23.)

The Legend of Sleepy Hollow, thru Oct. 31

Irving’s ‘Legend’ returns reimagined this fall. Performed for the first time ever outdoors under the stars at Washington Irving’s Sunnyside, master storyteller Jonathan Kruk will cast a spell with dramatic performances of the classic tale. Live music and an appearance from the Headless Horseman himself make this a spooky spectacular experience for all ages. Fridays-Sunday thru Oct. 31. Find tickets at hudsonvalley.org/events/irvings-legend/

Tour The Home of the Legend, thru Nov. 13

At this family-friendly happening, visitors can tour Washington Irving’s house — decorated for the season — watch an original shadow puppet short film, and enjoy games on the lawn. A special exhibit highlights how the  Legend  has lived in the imagination of popular culture through the centuries since its publication. Friday-Sunday through Nov. 13. Find tickets at hudsonvalley.org.

Sleepy Hollow 'Run For Your Life' Halloween 10K, Oct. 29

Experience historic and scary sites along the scenic Hudson River course. A best costume prize will be given. Advance registration at rivertownrunners.org. Kids race beings at 9 a.m., 10K at 9:30 a.m. at Morse School on Beekman Avenue.

Wednesday, May 01, 2024

sleepy hollow halloween tour

Sleepy Hollow, NY: Your Guide to Halloween Season

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sleepy hollow halloween tour

In recent years, travelers have finally learned that there is more to the great state of New York beyond our buzzing city. One place in particular has been on a lot of globetrotters’ radar, and that place is Sleepy Hollow, New York.

Where to go for Vacation in October

If you are like me seeking where to go for vacation in October, Sleepy Hollow is THE place to be in September and October.  It embodies all of the things that we love about the fall – the things that, quite honestly, we could really use after the last two years of pandemonium. Cozy little restaurants, an abundance of nature (leaf peeping!), and good old-fashioned Halloween fun!

Plus, it’s only an hour past New York City, making it accessible for East Coasters and those already visiting the area.

If Sleepy Hollow has been on your radar, use this guide to plan your perfect trip there this fall.

sleepy hollow halloween tour

Where is Sleepy Hollow?

Sleepy Hollow is a small village in the Hudson Valley area of New York State. It is so named because of the famous writer Washington Irving who lived in the area and wrote “The Legend of Sleepy Hollow.”

It’s important to note that Sleepy Hollow proper is actually quite small. The surrounding towns are only a few minutes away. They’re so close that you really won’t be able to tell where one begins and the next ends. Tarrytown, Elmsford, and Ossining are all suitable places to lodge and eat when visiting Sleepy Hollow.

sleepy hollow halloween tour

Sleepy Hollow Experiences.

Now, let’s look at some of the best things to do in Sleepy Hollow, New York:

The Great Jack O’Lantern Blaze:

Perhaps the most sought-after experience in Sleepy Hollow is the Great Jack O’Lantern Blaze. While many cities are offering similar experiences, there’s something extra special about visiting the one in ‘Halloween Headquarters.’

Your Guide to Halloween Season

Artists begin carving pumpkins in the summer and by October, THOUSANDS of them are lit and make their appearance for tons of spectators to enjoy. The level of intricate detail and craftsmanship is awe-inspiring. One of the most remarkable facets is how many pumpkins are used often to create one larger piece, such as a giant carousel, a re-creation of a famous art piece, or a cultural tapestry.

Grab tickets to this one early. It’s something that you’ll remember for a lifetime.

sleepy hollow halloween tour

Sleepy Hollow Cemetery Tours:

Typically we might think of cemeteries as places that are uncomfortable. The cemetery in Sleepy Hollow is one of the most beautiful that I’ve ever seen. It’s truly akin to an outdoor art museum as many of the crypts, tombs, and headstones are so intricately crafted, unique, and impossibly precise. Be sure to walk around during the day to gain a real appreciation.

However, at night, it’s imperative to take a spooky walking tour through the cemetery. You’ll hear all about the incredible ways that people who now lay in its confines perished and left this world. The tour guides even give you an old-style lantern to carry around as you hear each of the tales.

sleepy hollow halloween tour

Irving’s Legend:

The entire town of Sleepy Hollow exists largely because of “The Legend of Sleep Hollow.” It’s a horror story written by Washington Irving in the 19th century. It has since reached international fame, with the tale translated into a multitude of languages. Countless adaptations for the screen and stage having been created.

Sleepy Hollow Irving' s Legend

During Halloween season, watch one of the most gifted story tellers in the United States re-tell the beloved classic. He’ll leave you laughing, on the edge of your seat, and, of course, a little spooked.

Washington Irving’s Sunnyside Estate:

On a chilly fall day, there’s nothing more dreamy than touring the home and grounds of the infamous Washington Irving. Smiling attendants are usually selling warm cider and snacks for you to enjoy before or after your tour. Costumed docents walk you through the home. It’s fun to imagine the infamous American author, his family, and guests cozying up in the small rooms of the estate as the ghoulish wind whips by and the mighty river churns outside. Don’t forget to catch the finger puppet performance of “The Legend of Sleepy Hollow” while you’re there!

sleepy hollow halloween tour

Tarrytown Music Hall Ghost Tours:

The music hall theater is over 130 years old, so you know that there’s bound to be some interesting history. You can learn all about what went on during all of those years inside of the theater. Plus, you’ll hear about its many secrets, and best of all, learn about the other-worldly spirits that still haunt the premises. Guests are led by Gotham teams who allow their groups to use special advanced technology to find paranormal spirits within the music hall. What’s extra-spooky about this attraction, however, is the price tag attached…$135 per person. But, it’s an amazing experience!

Your Guide to Halloween Season

Sleepy Hollow Haunted Hayride:

This is another event that only takes place at the end of October. This year it’s on October 22nd and 23rd. The hay wagon takes guests down lively Main Street, past the Old Dutch Church, and into the spooky, dark woods of the hollow. The hayride retraces the path Ichabod Crane took as he tried to outrun the Headless Horseman.

sleepy hollow halloween tour

Farmer’s Markets:

TaSH Farmer’s Market and the Irvington Farmer’s Markets are the two in town to visit. Both feature just about every yummy and beautiful natural product you can imagine, from cheese to wine to bread to fresh-cut flowers. Locally grown produce makes a wonderful souvenir that won’t take up room in your living space nor gather dust for years to come.

sleepy hollow halloween tour

Hulda’s Night:

Everything here circles back to “The Legend of Sleepy Hollow.” In the story, the author mentions that the town was under the spell of a “high German doctor.” There are many who think that he’s alluding to a healer woman from Central Europe. She lived in Rockefeller State Park, and if you hike through Witch’s Spring Trail, you can walk by the area that used to be her dwelling.

Sleepy Hollow Hulda's Night

In this experience, guests go to that same trail and hear all about her life and story. Drinks and snacks are given at the end of the storytelling. Unfortunately, this is another one limited to just a few days at the end of October. It’s October 27 through 30th with two shows per evening at 6:00PM and 7:00PM.

Halloween Parade: 

Each year, towards the end of October, the Village of Tarrytown hosts a Halloween parade. It starts by Patriot’s Park and heads down Main Street. Afterwards, there’s a giant block party with a DJ and performances. Most people choose to wear their costumes, so don’t be shy about wearing yours!

The parade is on October 23rd this year at 5:30PM.

Sleepy Hollow Film Festival:

This year, the Sleepy Hollow Film Festival is from October 15th through the 17th. On the Sleepy Hollow waterfront, a pop-up drive-in theater will show pieces submitted by contestants. I’ll be updating this as more information comes out!

Sleepy Hollow Film Festival

Not Running for 2021.

The following experiences are unfortunately not running for the 2021 season, but I’ve included them for future visits to Sleepy Hollow.

Horseman’s Hollow:

This one is a ‘spooky walk’ or haunted house type experience. In front of the Philipsburg Manor is a re-created Sleepy Hollow village from the 1700s where everyone has ‘gone mad’ from the Headless Horseman. Costumed actors roam around and pop out to scare guests. There’s some serious talent in the construction of ‘haunted’ places like a chapel and spooky cabins.

sleepy hollow halloween tour

Sleepy Hollow Experience:

If you’ve ever been to an immersive theater show, then you know how utterly and insanely captivating the performances can be. This immersive version of “The Legend of Sleepy Hollow” often sells out but it is not to be missed. Guests follow all of the characters from the story through every scene of the tale, and even get to hang out and have some treats at the grand Van Tassel harvest party.

sleepy hollow halloween tour

Old Dutch Church Fest:

This event takes places on the grounds of the Old Dutch Church which is actually part of the setting of the Legend of Sleepy Hollow. Guests can buy sweets, ciders, beer, sausages, hot dogs, and souvenirs. Most proceeds go to the upkeep of the adjacent cemetery which houses graves of many folks, including patriots of the American Revolutionary War.

sleepy hollow halloween tour

If you’re familiar with Edgar Allan Poe, then you’ll at least remember hearing the phrase ‘nevermore.’ It comes from his chilling piece of writing entitled “The Raven.” Nevermore is a theatrical and aerial arts/circus-style adaptation of that Poe classic. Watch acrobats soar as they re-tell the story set to spooky music.

sleepy hollow halloween tour

Not-So-Spooky Places to Visit in Sleepy Hollow.

And finally, here are some things to do in Sleepy Hollow, New York that aren’t so spooky:

Sleepy Hollow Lighthouse Tours: 

The Sleepy Hollow Lighthouse has been in use for eighty years and was rendered obsolete in the early sixties due to the Tappan Zee Bridge being built with navigational lights which serve the same purpose as the lighthouse. Learn about the dozen or so lighthouse keepers and their families when you take a tour.

Sleepy Hollow lighthouse

The Octagon House: 

Few houses are more intriguing than the Armour-Stiner house. Built in the pre-Civil War period, its pink walls and unusual shape give the building a playful, antique, borderline spooky appearance. It’s modeled after the style of ancient temples and with such a storied history, it feels just as old. While you’re not able to visit and enter on your own, you can book a tour and learn all about the history of the house!

sleepy hollow halloween tour

If you’ve ever wondered how the other half lived, now is your chance. Kykuit was the home to four generations of Rockefeller family members. Thanks to the remaining descendants, guests have the opportunity to walk through the mansion and grounds on guided tours. You’ll truly be in awe as you see the modern amenities of the time that the family used inside their home as well as the many rooms (more than you’d even know what to do with) and their lavish aesthetic. Hearing stories about the family humanizes them a lot, as most people see them as celebrities. The house is furnished to look exactly as it would have when the original family members were living within its walls.

Kykuit

Old Dutch Church:

This church has a history that dates all the way back to the late 1600s. Its name comes from when the Dutch Merchant Company ruled New York before the British. Walk on the creaking floor boards, listen to the wind howl outside the fragile windows, and admire the centuries-old organ. Outside, you can explore the 2.5 acres of cemetery and rolling green land. The church is a focal point of Washington Irving’s classic, “The Legend of Sleepy Hollow.”

sleepy hollow halloween tour

Union Church of Pocantico Hills:

This church really just fits the entire aesthetic of Sleepy Hollow. It has a rustic charm that fits right into the surrounding nature. It also has a bit of a storied history connecting directly to the Rockefeller family and Henri Matisse. There are usually events here such as book sales where you can find gently used novels for a dollar apiece.

sleepy hollow halloween tour

If you’re into castles that looked as though they’re plucked from the pages of a storybook, then you’ll really enjoy Lyndhurst. Built in the mid-1800s, it’s had a few ‘who’s who’ of owners, including Jay Gould, the railroad baron. Take a tour of the opulent inside, walk around the gardens, and partake in the many fairs that take place on the grounds.

sleepy hollow halloween tour

Places to Stay in Sleepy Hollow.

To fully experience Sleepy Hollow, you’ll need to spend a few days there. I recommend booking your hotel well in advance if you plan to visit during the busy Halloween season!

Budget Option:

Don’t want to break the bank? No problem, book a stay at…

We’ve snagged a room here for under $100 and enjoyed it very much. It’s no frills, but warm, cozy, and a fine place to watch Hocus Pocus after a cemetery walk or evening meal.

Days Inn near Sleepy Hollow

Moderate Options: 

If you want a few more amenities, consider one of these mis-range accommodations:

Comfort Inn and Suites:

Very clean, and extremely comfortable beds. The best part about staying here is the great amount of space that you’ll have. That’s especially important if you’re traveling with a family.

Comfort Inn near Sleepy Hollow

Courtyard Marriott:

A fireplace in the lobby and lots of space for relaxing, enjoying a quick breakfast, or getting some work done makes this a comfortable option. Guest rooms are clean, usually come with a desk, and offer just enough space (although not a ton of it).

sleepy hollow halloween tour

Hampton Inn:

If you’ve stayed at a Hampton Inn, then you know. Clean and a decent amount of space. There are sundries for sale if you need some snacks or basic toiletries.

sleepy hollow halloween tour

Luxury Options:

Finally, if you want to stay in style, check out one of these options:

Hotel Nyack:

If you’re into hotels with aesthetic appeal, this is the place for you. It’s industrial enough to feel as though it belongs somewhere in Brooklyn, yet offers balcony views of the Hudson River. The rooms feel extra luxurious with chandeliers, high-backed chairs, and wallpaper that gives serious ‘boudoir’ vibes.

Hotel Nyack near Sleepy Hollow

Sleepy Hollow Hotel & Conference Center:

Roaring stone fireplaces, high wooden beamed ceilings, and dark cherry stained features make this place feel  like it belongs in Sleepy Hollow. Cool amenities include a gorgeous indoor pool and gym. The rooms are oh-so-spacious and full of warm, autumn colors.

sleepy hollow halloween tour

Tarrytown House Estate:

This estate boasts over 200 guest rooms and 10 Georgian style rooms. The ambiance is minimalist meets artistic, and the pale colors and bursts of white make it feel sparkling clean. The King House Mansion which houses some of the rooms was constructed in 1840. There’s a basketball court, horseshoe court, tennis court, indoor and outdoor pools, a restaurant, and a fitness center.

Tarrytown House Estate near Sleepy Hollow NY

Castle Hotel and Spa:

This place is quite literally a castle. It’s decorated with cozy fireplaces, luxurious comforters on four-poster beds, and candelabras hanging from the ceilings. With sweeping views of the New York City skyline, Hudson River, and Palisades, this makes it an extra luxurious option for lodging.

sleepy hollow halloween tour

Places to Eat in Sleepy Hollow.

Of course, no travel guide would be complete without discussing local food options!

Pik Nik BBQ:

My personal favorite spot for lunch! It’s a full sensory experience with perhaps the best playlist ever created, the smell of smoked meats wafting through the air, and the taste of slow roasted pork, creamy mac and cheese, and tangy apple coleslaw. Ribs, chicken, andouille sausage, burnt ends, cornbread, potato salad, everything barbecue classic is available for your gastronomic pleasure. Be aware that space can be limited.

Sleepy Hollow Pik Nik BBQ

Lefteris Gyro:

Another exceedingly popular spot that has limited seating, but at least it’s both indoor and outdoor. I love this place, and from experience I can say that you need to order enough food so that you can literally roll out when you’re done. The shrimp saganaki is potent, pungent, and bursting with flavor — personally I’d choose it every time. If shrimp isn’t your thing, don’t worry, there’s what feels like dozens of other options, much more than your typical Greek restaurant. The avgolemono soup (lemon chicken) warms both the bones and the soul. It’s a nice light option. Have a glass of wine with dinner and a Greek frappe or coffee (careful there) for after your meal.

sleepy hollow halloween tour

Goosefeather: 

This restaurant has both indoor and outdoor seating and is a MUST if you’re looking for savory, decadent, comfort food. The menu is Hong Kong inspired and you’ll want to order the shaved snow peas, sweet summer corn, and Cantonese roast duck, in addition to the delicious dim sum offerings. For dessert? Mochi waffles, of course.

sleepy hollow halloween tour

Horsefeathers:

Dimly lit, warmly inviting, and Halloween-esque, this is a MUST visit in Sleepy Hollow. Cider, beer, and adult juice boxes are the name of the game in terms of booze. For sustenance, you can visit for brunch, lunch, or dinner. The menu feels endless (there are over a hundred items) and includes lots of options by way of pasta, meat and poultry, seafood, burgers and sandwiches, and salads. When dessert rolls around, opt for a boozy coffee — there are seven versions to choose from!

sleepy hollow halloween tour

Guadalajara:

Make reservations in advance, because this popular Mexican eatery is packed nearly every night in October. Whatever you order, rest assured that it will be awesome. In my humble opinion, you have to start your meal off with the guacamole prepared table-side and the queso fundido (the best I’ve ever had). The tortilla soup is a heavenly second course and although you’ll be full, make room for an entree — it’s worth it. Margaritas pack a punch here and come in a variety of flavors.

Visiting during October is extra special because every staff member dresses up in costume complete with elaborate make up!

sleepy hollow halloween tour

Sweetgrass Grill:

The food at this light, airy beach restaurant is seasonal and locally sourced from farms nearby. For brunch try the lemon blueberry waffle or the heirloom tomato hash (yum!). Salads and sandwiches make up the majority of the menu which makes this a great lunch spot (even for takeout).

sleepy hollow halloween tour

Tarry Tavern:

Situated right on Main Street, this place isn’t a bad choice at all for a lunch with some upscale options. Picture a place that serves comfort food, and then levels up that comfort food — like mac and cheese with crab meat and white truffle, for instance. Pork cheeks, sea scallops, burrata cheese, duck confit fettuccine, and Amish roasted half-chickens are just a fraction of the elevated comfort food that makes up this menu.

sleepy hollow halloween tour

J.P. Doyle’s:

A beer garden meets Irish tavern that has all of the classics – burgers, Reubens, potato skins, and more. Don’t miss their brunch or taco Tuesday specials – that one comes served with a side of trivia!

sleepy hollow halloween tour

Bridge View Tavern:

Despite being a ‘tavern,’ the fare goes way beyond buffalo wings and mozzarella sticks. Try options like fig and goat cheese flat bread, curry vegetables, a wild boar chorizo burger, or elk burger. This is by no means an exhaustive list of entrees, but as you can see, the menu is anything by typical. Of course you’ll want to get a beer, cider, or mixed drink, such as a grapefruit martini, to wash it all down.

sleepy hollow halloween tour

Hudson Farmer and the Fish:

Hudson Farmer and the Fish sits on the Hudson’s riverbank and featured a seasonal menu. Unsurprisingly given the restaurant’s name, there’s a heavy focus on locally sourced seafood – both raw and cooked. There’s also a pizza menu selection that will have you saying, “well…what’s the harm in ordering ALL of them?” Good luck deciding between options like the Clam (clams, bacon, celery, onion, thyme, garlic, fontina and parmesan) or the Mushroom (truffle, arugula, fontina, and portobello mushrooms).

sleepy hollow halloween tour

Hudson Anchor Seafood and Grill:

Looking for a meal with a gorgeous view? You’ve found the right place. The menu has some more ‘mature’ offerings like panzanella salad, paella, and seafood risotto, but by no means is the atmosphere stuffy. String lights, wide umbrellas, and decorative fall touches like hay bales and corn stalks give this place an intimate, laid-back vibe.

sleepy hollow halloween tour

Coffee and Such in Sleepy Hollow.

If you just need a cup of coffee and a snack, head to one of these local gems:

Coffee Lab Roasters:

An absolute favorite among locals and visitors alike, maybe because it’s puppy themed?! Enjoy knock out coffee and pastry options like almond or chocolate croissants, Scottish short bread, and cake pops. They offer unique and healthy coffee options like CBD vanilla and golden turmeric.

Coffee Lab Roasters in Sleepy Hollow

Muddy Water Coffee & Cafe:

Whether you want a cozy meal, sweet pastry, or just a coffee pick-me-up — this is a great spot for something quick and something that is made with love and care!

sleepy hollow halloween tour

Places to Drink in Sleepy Hollow.

And finally, you’ll likely want to check out some of the area’s breweries after a long day of exploring!

Sing Sing Kill Brewery:

Looking for a brewery that doesn’t frown on bringing your kids along? Visit Sing Sing! Enjoy decadent options like Cherry Chocolate Milk Stout or Killer Cream Ale and get some hot dogs and soft baked pretzels to go with your brews.

Speaking of kids, here’s what you need to know if you’ll be visiting Sleepy Hollow with little ones.

sleepy hollow halloween tour

Beekman Ale House:

Beekman Ale House knows that the people love Halloween! Throughout the month of October, Beekman’s celebrates Pumpkin Fest with a series of rotating beers on tap that are all pumpkin flavored. When you’re getting good and buzzed, order any of the five twelve-inch pies on the menu (hot oil flavor is a good choice) or classic apps like mozzarella triangles and wings. The wooden interior and neighborhood vibe give this bar a cozy, fun ambiance.

sleepy hollow halloween tour

Captain Lawrence Brewing Company:

As far as craft beers go, Captain Lawrence is becoming increasingly popular. With flavors like Autumn Blaze Pumpkin Ale, Golden Delicious Tripel, and a host of IPAs and sours, it’s no surprise. Aside from tasting fantastic brews, Captain Lawrence Brewing Company offers fun opportunities like trivia nights and live music.

sleepy hollow halloween tour

People to Follow.

Want to know more about Sleepy Hollow and the neighboring areas and attractions? These are the places I turn to get excited about the upcoming season! Follow these accounts on social media:

Sleepy Hollow Spellbound 

sleepy hollow halloween tour

Visit Sleepy Hollow  

sleepy hollow halloween tour

Tarry In Town

sleepy hollow halloween tour

TarryHollow Town  

sleepy hollow halloween tour

  • September 16, 2021

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Stephanie Amb

Stephanie is a writer of travel, fiction, and New York lifestyle. She currently lives in Brooklyn and teaches full time in Queens. She is a wife and mother to one son. Stephanie is a co-founder at Tawk of New Yawk and her work has been featured in Your Life is a Trip, Teaching Traveling, and Literary Traveler.

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The Hudson Indy Westchester's Rivertowns News - - Sleepy Hollow, Tarrytown, Irvington, Dobbs Ferry

Ultimate Guide to Halloween 2021 in Sleepy Hollow and the Rivertowns

By Brianna Staudt —

Whether you’re a local anticipating a favorite Halloween tradition or a visitor looking to experience Halloween in Sleepy Hollow Country for the first time, The Hudson Independent has you covered. Read below for all the tricks, treats and haunts in Sleepy Hollow, Tarrytown, Irvington, Dobbs Ferry and the surrounding area.

Please note this list will be updated as additional events are confirmed. Required pandemic precautions are included.

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The Tarrytown Halloween Parade and block party have been cancelled.

Horseman’s Hollow, the Old Dutch Church Fest and Jay Ghoul’s House of Curiosities are also not running this year.

The Sleepy Hollow Tarrytown Chamber of Commerce is staffing its office at 1 Neperan Road in Tarrytown on Saturdays 9 a.m.–1 p.m. throughout the fall to help visitors navigate local businesses. Stop by for maps, recommendations and parking information.

TarryHollow Walking Tours Tour #1 starts at 11 Dell Street/418 North Broadway Sleepy Hollow Sept. 5-Nov. 14, Saturdays and Sundays; 10 a.m., 12:30 p.m. 3 p.m. $24.99/ticket https://www.thehistoricalsociety.net/events/tours-tarryhollow/ Travel back in time with the Tarrytown and Sleepy Hollow historical society on a 1.5- or 2-hour tour of the area. The Hudson Independent recommends Tour #1: “TarryHollow: Irving, the Old Dutch Church and the Colonial Experience” for Halloween fun, though there are three popular tours available. Arrive 15 minutes early for check-in. Advance reservations required; purchase tickets online. Private tours available.

Evening Lantern Tour Sleepy Hollow Cemetery North Gate 540 North Broadway Sleepy Hollow Friday and Saturday nights in September; every evening in October; weekends and select weekdays in November. Times vary. $30 https://www.showclix.com/event/classic-evening-lantern-tour-2021 Explore the historic Sleepy Hollow Cemetery by the light of a kerosene lantern. This one-hour tour focuses on the north end; visit during the day to see Irving’s grave. Ages 10 and up.

The Great Jack O’Lantern Blaze Van Cortlandt Manor 525 S. Riverside Croton-on-Hudson Sept. 17-Nov. 21, select nights $24; members and children 2 and under are free https://hudsonvalley.org/events/blaze/ Breath-taking display of over 7,000 jack-o’-lanterns, which are hand-carved and arranged on-site. New installations for 2021 include the New York City skyline and an “immersive” river display. Tickets must be purchased in advance.

Champagne Cocktails with the Dead Sleepy Hollow Cemetery – North Gate 540 North Broadway Sleepy Hollow Sept. 26 and Oct. 3, 5-7:30 p.m. $85 https://visitsleepyhollow.com/events/champagne-cocktails-with-the-dead/ Peak inside mausoleums and learn family histories, champagne cocktail and/or light refreshment in hand. No jeans or shorts, but comfortable walking shoes are recommended. For ages 21 and up; masks required in the mausoleums.

Fall Reflections: An Installation Lyndhurst Mansion, Rockery Pathways 635 S. Broadway Tarrytown Sept. 30-Oct. 31, 9:30 a.m.-4:30 p.m. Free with purchase of a grounds pass ($10; children 6 and under and Lyndhurst Members are free) https://lyndhurst.org/events/outdoor-decor/ Discover witches and other spirits in the fall landscape south of the mansion. New for 2021: a special art installation from LiteMirror .

Home of the “Legend” Washington Irving’s Sunnyside GPS address: 3 West Sunnyside Lane Irvington Oct. 1-Nov. 8, Fridays-Sundays and Columbus Day; entries 10 a.m. – 3:30 p.m. $10-$12 https://hudsonvalley.org/events/home-of-the-legend/ Tour the first floor of Irving’s home and learn how “The Legend of Sleepy Hollow” has lived on in popular culture. Family friendly.

Irving’s “Legend” Washington Irving’s Sunnyside GPS address: 3 West Sunnyside Lane Irvington Fridays-Sundays Oct. 1-31, 6:30, 8 and 9:30 p.m. $24-$35 https://hudsonvalley.org/events/irvings-legend/ Master storyteller Johnathan Kruk performs “The Legend of Sleepy Hollow.” Live music and an appearance by the Headless Horsemen himself. Tickets required and must be purchased online in advance. Appropriate for all ages.

“Myths and Mysteries” Tour  The Armour-Stiner Octagon House 45 W. Clinton Ave. Irvington Oct. 1-31; multiple dates and times $27-29 https://www.showclix.com/event/myths-mysteries Explore this 1860 historic home with a one-hour tour featuring its “connection to the spiritual world,” including “unexplained and uncanny” events. Is there a resident ghost? Masks required; not suitable for individuals with mobility difficulties.

Pumpkin Painting and a Hayride Devries Park 139 Devries Ave. Sleepy Hollow Oct. 2, 11 a.m.-12 p.m. or 12-1 p.m. Free Paint and decorate a pumpkin (pumpkin and supplies provided) and take a hay ride around the park. Presented by the Sleepy Hollow Department of Recreation. Email [email protected] or [email protected] to reserve your time slot. 100 children only per time slot.

Halloween: A Haunted History Virtual Presentation Oct. 4, 7 p.m. over Zoom Free This new program traces the “strange history” of Halloween, from Old World festival to modern holiday. Presented by the Warner Library. Registration required.

Halloween Crafts Warner Library 121 North Broadway Tarrytown Oct. 6, 4 p.m. Free Come to the children’s garden to make spooky — not scary — Halloween decorations using recycled materials. For ages 3 and up. Registration required and limited. Call the children’s desk.

Murder & Mayhem Sleepy Hollow Cemetery North Gate 540 North Broadway Sleepy Hollow Thursdays, Oct. 7-Nov. 11; 7:30-9:30 p.m. $45 https://www.showclix.com/event/murder-mayhem-2021 Two-hour, lantern-light walking tour of the cemetery’s darker history, including the scene of a grave robbery and victims of  the “Mad Murderer of Sleepy Hollow.” Ages 18 and up. Please note this event is an approximately 1.5-mile walking tour in the dark that includes steep hills and stairs.

Scarecrow Making Parking Lot D (to the right of the recreation department) 238 W. Main St. Tarrytown Oct. 9, 10:45-11:45 a.m. or 12-1 p.m. Free Register by Oct. 7 at this link (space is limited): https://tarrytown.seamlessdocs.com/f/qyeh2no2hgky Make a scarecrow to be displayed by the village along Main Street or Broadway. Straw, bags, ties and frames will be provided. Participants bring their own clothing, scissors and markers. Participants may also choose to pick up supplies, build their scarecrow at home, and drop it off by 1:30 p.m. Masks required.

Paint your own Witchy Wonderland Washington Irving Memorial Chapel 540 North Broadway Sleepy Hollow Oct. 9, 12-3 p.m. $65 https://www.showclix.com/event/paint-your-own-witchy-wonderland-2021 Join painter Heather Gleason to create your own Halloween canvas — paint, brushes, canvas and light refreshments included. Age 18 and up. This event takes place inside and requires masks regardless of vaccination status.

Halloween Slime Warner Library 121 North Broadway Tarrytown Oct. 12, 4 p.m. Free Gather in the children’s garden to make a jar of Halloween slime. For grades 1-5. Registration is required and limited. Call the children’s desk.

Sleepy Hollow International Film Fest Kingsland Point Park Sleepy Hollow Oct. 15-17; cars may arrive starting 5:30 p.m., first feature at 7:30 p.m. $25/car each night http://sleepyhollowfilmfest.com/horseless-carriage-cinema/ Outdoor double-features and food trucks. Movies include The Thing and Arachnophobia — see website or flyer for complete list of titles per night. Must purchase tickets in advance online and bring a printed copy. Audio available via radio; if you’re not planning to view the movie from inside your car, make sure you have a device that picks up FM radio.

Outdoor Screening of Hocus Pocus Main Street School Lawn 101 Main Street Irvington Oct. 15; Doors open for “treats” and a red carpet at 5:30 p.m., movie starts at sunset $5/ticket (must be purchased in advance via website) https://www.irvingtontheater.com/hocuspocus Presented by the Irvington Theater as part of its “Sunset Cinema” series. Attendees should bring blankets and chairs. Outside food is allowed, however, there is no alcohol allowed on school grounds. Don’t forget your costume!

Mary Shelley’s Frankenstein Washington Irving Memorial Chapel 540 North Broadway Sleepy Hollow Oct. 16, 5:30-7 or 8-9:30 $25 https://www.showclix.com/event/mary-shelley-s-frankenstein-2021EttIsCo Enjoy an adapted presentation of this classic tale. Event is seated indoors; masks required regardless of vaccination status.

“Trunk-or-Treat” Lot F (parking lot between the boat club and Losee Park) Green Street Tarrytown Oct. 17, 4:30-6:30 p.m. Free Drive-thru format: families drive through the lot to view the decorated trunks and pick up treats along the way. Register your decorated vehicle to distribute candy on the Tarrytown Recreation website by Oct. 14. Contest for best vehicle. Presented by the Tarrytown Recreation Department.

Harvest Hayride Matthiessen Park 1 Bridge St. Irvington Oct. 17; family rides 6-7 p.m., haunted rides 7-8:30 p.m. Free Come for a horse-and-wagon ride, refreshments and music by the Blu Road Orchestra Band. Masks must be worn while waiting online. No dogs. No pre-registration required. Presented by the Irvington Recreation Department.

Halloween Window Painting Main Street and Broadway Tarrytown Oct. 20, 3:30-5:30 p.m. Free https://www.sleepyhollowtarrytownchamber.com/event-details/tarrytown-halloween-window-art-1 Help paint store windows on Main Street and Broadway! Children pickup paint in front of CVS on North Broadway between 3:30-4:30 p.m. Reserve your window at the link above — registration required. Parent/guardian supervision, masks and social distancing required. Presented by the Tarrytown Recreation Department.

Halloween Party Warner Library 121 North Broadway Tarrytown Oct. 21, 4 p.m. Free Gather on the front lawn in costume for a story, treats and crafts. Ages 3 and up.

Halloween Terrariums Irvington Library 12 S. Astor St. Irvington Oct. 21, 5:30-6:30 p.m. Free Make something fun (and a little spooky) for Halloween. In the program room; masks required. For grades 6-12. Registration required.

Pumpkin Painting for Teens/Pre-Teens Dobbs Ferry Library Terrace 55 Main St. Dobbs Ferry Oct. 22, 4:30-6 p.m. Free Paint a miniature pumpkin outside on the terrace. Light food and beverages provided. E-mail [email protected] to register.

Sleepy Hollow Block Party Beekman Avenue Sleepy Hollow Oct. 22-23, starting 5 p.m. Free Vendors, music and more

Haunted Hayride Sleepy Hollow Village Hall/Firehouse 28 Beekman Ave. Sleepy Hollow Oct. 22-23, 7 p.m. – 12 a.m. $40/ticket; $20 rate for Public Schools of the Tarrytowns students if tickets purchased at Village Hall before noon Oct. 22 with student ID. https://sleepyhollowny.ticketleap.com/2021-sleepy-hollow-ny-haunted-hayride/ Face masks required. This event is not recommended for some children due to graphic content. Tickets required and must be purchased online in advance. Act fast — tickets sell out!

Sleepy Hollow Halloween 10K & Kids Fun Run W. L. Morse School 30 Pocantico St. Sleepy Hollow Oct. 23, 10K 9:30 a.m.; Fun Run 9 a.m. $40 registration through Oct. 17; $50 registration on race day. $5 for Fun Run. http://www.rivertownrunners.org/sleepy-hollow-10k/ This 10K winds through historic Sleepy Hollow with sites including the Sleepy Hollow Cemetery, the Old Dutch Church, the Headless Horseman Bridge and a beautiful stretch along the Hudson River. Registration capped at 1,500 runners. Mile-long Kids Fun Run is for ages 6 and older includes a finisher medal. Costumes encouraged for runners of all ages but not required. Live music, and beer tasting for runners age 21 and older. Please note no strollers, inline skates or pets are allowed.

Outdoor Halloween Movie Night: Hotel Transylvania Pierson Park 238 W. Main St. Tarrytown Oct. 23, movie starts at 6:30 p.m. Free Popcorn will be served. Bring blankets and chairs. Attendees are encouraged to support local restaurants and bring meals and snacks to the movie. Presented by the Tarrytown Recreation Department. No tickets or registration required.

Ghost Tours of the Music Hall Tarrytown Music Hall 13 Main Street Tarrytown Daytime tours Oct. 24; late afternoon and evening tours Oct. 27-28 $25 https://tickets.tarrytownmusichall.org/eventperformances.asp?evt=2508 “Balcony to backstage” guided ghost tour of the 136-year-old theater. Vaccinated patrons only. Masks required. Flashlights provided for all attendees courtesy of Key Bank. Please note the tour requires stair climbing and standing for extended periods.

Downtown Halloween Window Painting Contest Cedar and Main Streets Dobbs Ferry Oct. 24, 10 a.m.-2 p.m. $5/individual (2nd-8th grades); $7/team (2 people 2nd-8th grades); $10/family (up to five immediate family members) www.dobbsferry.activityreg.com Decorate storefront windows as individuals, teams or families to compete for best in division or three overall prizes: “Most Original,” “Most Whimsical” and “Best Halloween Concept.” Presented by the Dobbs Ferry Recreation Department. Open to Dobbs Ferry residents and Dobbs Ferry school district students only. Must register by noon on Oct. 22. See link above for registration and official contest rules.

2nd Annual SUP Witch Paddle Horan’s Landing 57 River Street Sleepy Hollow Oct. 24, 1 p.m. Free if you own your own SUP board or kayak; $35 to rent equipment https://rivertownssupyoga.com/sup-witches-2021-2 Costume Required. Come to Horan’s Landing to hear a telling of the Legend of Sleepy Hollow. Then, launch with other witches at 5 p.m. on a paddle along the Hudson River shoreline. Paddle experience required. Spectators welcome; the RiverWalk is a prime location to view the paddle. See the Wishing Wall while you’re there.

Halloween Origami Dobbs Ferry Library 55 Main St. Dobbs Ferry Oct. 25-31 Free Stop by the children’s room and check out a special Halloween origami station — fold paper bats, ghost and black cats! Ages 7 and up.

Halloween Story-Time Irvington Library 12 S. Astor St. Irvington Oct. 26, 4-4:45 p.m. Free Come in costume for a story and a treat! In the library garden. Registration required. For ages 4 and up.

Hulda’s Night Rockefeller Park Preserve 25 Sleepy Hollow Road Sleepy Hollow Oct. 27-30; 6 and 7 p.m. programs $28 https://www.friendsrock.org/huldas-night Guided tour through the dark woods to Hulda’s home, where she will tell her story. You’ll meet “The Leatherman” along the way — maybe some other friends, too. Bring a flashlight. No children under 10.

Irving’s Nightmare Presents: The Spider Lab 26 Irving Ave. Tarrytown Oct. 27-31; 6-10 p.m. Free https://www.facebook.com/IrvingsNightmare/ Elaborate local “yard haunt” that never disappoints.

Riverside Haunts The Good Witch Coffee Bar 134 Southside Ave. Hastings-on-Hudson Oct. 28-29, 7 p.m. $25 https://www.eventbrite.com/e/riverside-haunts-scary-stories-to-tell-by-the-hudson-tickets-166176336897 River’s Edge Theater Company hosts two nights of scary storytelling, history and live music outdoors. Recommended for mature audiences only. 10 percent of ticket sales benefit Riverkeeper.

Field of Screams Firehouse Basement 112 Main Street Dobbs Ferry Oct. 29, 7-9 p.m. Free Can you make it through without being scared? Enter on Main Street in front of the police station. Geared toward children age 8 and up. Presented by the Dobbs Ferry Recreation Department. Masks required. This event is usually held at the park but has been moved indoors due to inclement weather.

Halloween in the Children’s Room Dobbs Ferry Library 55 Main St. Dobbs Ferry Oct. 29-31 Free Come in costume and pick out a prize! Ages 0-12.

Halloween at the James Galgano Senior Center 55 Elm Street Sleepy Hollow Oct. 30, 1 p.m.–5 p.m. Free Halloween crafts and treats and photo booth, 1 p.m. in the senior center;  “Truck-or-Treat” in the parking lot, 3–5 p.m. Kids of all ages welcome. No pre-registration required. Presented by the Sleepy Hollow Recreation Department.

Pet Parade Dobbs Ferry Waterfront Park 87 Ogden Park Dobbs Ferry Oct. 31, 11:30 a.m. Free Dress up your pet and meet at the flagpole for a loop around the park to show off their costumes. Dogs must be leashed. Masks recommend for unvaccinated individuals. Presented by the Dobbs Ferry Recreation Department.

Howl-O-Ween Bash Dobbs Ferry Waterfront Park 87 Ogden Park Dobbs Ferry Oct. 31, 12-4 p.m. Free Inflatables, a petting zoo, mini-golf, food trucks and live music by Al Indig & Friends and Marguerite & co. Masks recommend for unvaccinated individuals. Presented by the Dobbs Ferry Recreation Department.

“Howl-O-Ween” Kids Parade 30 Pocantico Street Sleepy Hollow Oct. 31, 3:30 p.m. Free Meet at W. L. Morse School. Candy and prizes — get those costumes ready! Kids of all ages welcomed. No pre-registration required. Presented by the Sleepy Hollow Recreation Department.

Downtown Trick-or-Treating Cedar and Main Streets Dobbs Ferry Oct. 31, 4-6 p.m. Free Music by Rooney Tunes. Masks recommend for unvaccinated individuals.

Irvington Halloween Parade North Broadway and Main Street Irvington Oct. 31, 4 p.m. Free Families should gather in Immaculate Conception Church parking lot. (No pets, please!) The parade will proceed down Broadway and Main until Main Street School. Children can pick up a free treat bag courtesy of the Irvington Fire Company. Presented by the Irvington Recreation Department.

Halloween Bands Downtown Irvington Irvington Oct. 31 evening Free Check out local musical talent perform crowd favorites live in costume on front porches. This much-anticipated event is an annual tradition. Here’s the current lineup: Wild Thyme, Barn Owls, North Dutcher All-Stars, and Evil Eckar w/Death Island and the Dirty Irv Horns. Expect at least one other band on the 31st.

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sleepy hollow halloween tour

living after midnite

Halloween , Lifestyle , Travel , Westchester · August 14, 2023

Halloween in Sleepy Hollow Country

four women at Headless Horseman Bridge in Sleepy Hollow Cemetery

If you’ve been following me for a while then you know I’m KINDA THE QUEEN OF HALLOWEEN! We’re just a few weeks away from the start Fall and that means that Halloween is right around the corner.

If you’re as Halloween obsessed as I am then you’ve definitely heard of the town of Sleepy Hollow. Located 25 miles north of New York City along the eastern shore of the Hudson River, the Village of Sleepy Hollow was immortalized in Washington Irving’s famous tale, “The Legend of Sleepy Hollow” and is now a modern village that is home to 10,000 residents.

Horsefeathers Restaurant | Where to Eat in Sleepy Hollow | Halloween in Sleepy Hollow Country | The Best Things to Do in Sleepy Hollow | The Legend of Sleepy Hollow | Sleepy Hollow Travel Guide | Tarrytown, New York | Westchester County New York Halloween Activities Near New York City | Headless Horse | Cemetery Tours | The Great Jack O Lantern Blaze | Hudson Valley Halloween

Sleepy Hollow was given its name by its original Dutch settlers for its dreary atmosphere and supernatural occurrences surrounding witches and other ghouls. One folklore in particular – the Headless Horseman – was a Hessian solider and is a ghost without a head that rides around on horseback only at night.

FUN FACT: Sleepy Hollow is considered be some to be one of the “most haunted places in the world”, but also has been designated “the safest small ‘city’ in America”.

I think all of the above makes it pretty obvious why it’s a great idea to celebrate Halloween in Sleepy Hollow Country! Also, it’s a great destination for those who love Halloween (like me!) and as you scroll through the rest of this post you’ll see how Sleepy Hollow Country offers a wide range of Halloween events and activities for all ages.

three women at the bar for a photoshoot for Halloween in Sleepy Hollow Country

The Great Jack O Lantern Blaze

The Great Jack O Lantern Blaze | Halloween in Sleepy Hollow Country | The Best Things to Do in Sleepy Hollow | The Legend of Sleepy Hollow | Sleepy Hollow Travel Guide | Tarrytown, New York | Westchester County New York Halloween Activities Near New York City | Headless Horse | Cemetery Tours | Hudson Valley Halloween

  • One of the COOLEST Halloween experiences in the country with more than 7000 illuminated jack o’ lanterns are on display.
  • The Blaze is a walk-through experience where thousands of hand carved pumpkins in elaborate displays light up the night. Includes large than life installations, along with synchronized lighting to an original soundtrack.
  • Located at the historic, Van Cortlandt Manor in Croton-on-Hudson (they also have a second location now in Nassau County, Long Island at Old Bethpage Village Restoration)
  • Also, it runs from September 15th – November 19th
  • You can walk at your own pace and stay as long as you like, but typically it takes around 45 minutes to an hour for the entire experience.
  • Advanced Tickets required!
  • Moreover, all proceeds from The Blaze support the programs of Historic Hudson Valley.
  • Family Friendly!
  • Free parking available on site.
  • 525 S Riverside, Croton-on-Hudson, NY 10520

pumpkin with light in Halloween in Sleepy Hollow Country

Visit Sleepy Hollow Cemetery

  • Founded in 1849, this private cemetery is 90 acres big and home to over 45,000 interments.
  • Famous burials include Washington Irving, Andrew Carnegie, Walter Chrysler, Samuel Gompers, Elizabeth Arden, Leona Helmsley, Brooke Astor, and William Rockefeller. 
  • So, the grounds are open daily from 8am to 4:30pm and you may walk or drive through on your own. Also, free maps, perfect for a self guided tour to major figures in the cemetery are available at both entrances.
  • They also offer a variety of tours at the cemetery. (Scroll down for more info!)
  • Gentle reminder to be respectful when visiting the Sleepy Hollow Cemetery – This is a private cemetery and you should act as if you are attending the funeral or grave of a beloved relative or friend. Use caution when driving and parking throughout the cemetery. They prohibit picnicking, sunbathing, littering, smoking, vaping, alcohol and drugs.
  • There is a small lot to park in near the South Gate and parking is allowed along the cemetery roads. Make sure not to park on the grass or graves throughout the cemetery.
  • 540 N. Broadway, Sleepy Hollow, NY 10591

Sleepy Hollow Cemetery | Halloween in Sleepy Hollow Country | The Best Things to Do in Sleepy Hollow | The Legend of Sleepy Hollow | Sleepy Hollow Travel Guide | Tarrytown, New York | Westchester County New York Halloween Activities Near New York City | Headless Horse | Cemetery Tours | The Great Jack O Lantern Blaze | Hudson Valley Halloween

Guided Tours through the Sleepy Hollow Cemetery

If you’re spending Halloween in Sleepy Hollow Country you’ll definitely want to book a cemetery tour. There are MANY different guided tours offered at the Sleepy Hollow Cemetery throughout September, October & November. Advanced tickets for all events are required and can be found HERE !

I highly suggest going on one of the night tours because the only time visitors are allowed in the park at night is on a tour!

Evening Lantern Tour at Sleepy Hollow Cemetery | Halloween in Sleepy Hollow Country | The Best Things to Do in Sleepy Hollow | The Legend of Sleepy Hollow | Sleepy Hollow Travel Guide | Tarrytown, New York | Westchester County New York Halloween Activities Near New York City | Headless Horse | Cemetery Tours | The Great Jack O Lantern Blaze | Hudson Valley Halloween

Classic Daytime Tour

  • 2 hour daytime walk through the cemetery.
  • Every Saturday & Sunday 2-4pm through November 27th.
  • Route is approx. 1.5 miles and includes hills, stairs and unpaved roads.
  • Sleepy Hollow Cemetery South Gate – 540 N. Broadway, Sleepy Hollow, NY 10591
  • Free Parking!

Classic Evening Lantern Tour

  • 2 hour evening tour that gives you a great overview of why Sleepy Hollow Cemetery is so famous.
  • Fridays & Saturdays from 8-10pm in September. Fridays, Saturdays & Sundays in October from 7-9pm & 10pm-12am.
  • Best for Ages 10+
  • The Daytime & Evening Tours are the same route with the same content, they just start in a different location.
  • Sleepy Hollow Cemetery North Gate – 540 N. Broadway, Sleepy Hollow, NY 10591

The Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow” Tour

  • Learn all about Washington Irving and his impact on American Literature and “The Legend of Sleepy Hollow”
  • 1 Hour tour exploring the South End of the cemetery.
  • Route includes hills, stairs and unpaved roads.
  • Saturdays & Sundays from 11am-12pm & 1-2pm through November 26th. In October this tour is offered everyday from 1-2pm.

American Aristocrats Tour

  • 1 hour lantern tour where your meet some of the American Aristocrats, like William Rockefeller & Andrew Carnegie, who shaped our country with their ambitious visions and amassed sizable fortunes.
  • Friday and Saturday evening in September from 8:30-9:30pm. Daily in October from 7:30-8:30pm, also 9:30pm-10:30pm on Saturdays and Sundays in October. Select dates in November.

These are just a few of the many guided tours offered at the cemetery, click HERE for more including Champagne Cocktails with the Dead, Murder and Mayhem and Murder Mystery.

Washington Irving Grave Evening Lantern Tour at Sleepy Hollow Cemetery | Halloween in Sleepy Hollow Country | The Best Things to Do in Sleepy Hollow | The Legend of Sleepy Hollow | Sleepy Hollow Travel Guide | Tarrytown, New York | Westchester County New York Halloween Activities Near New York City | Headless Horse | Cemetery Tours | The Great Jack O Lantern Blaze | Hudson Valley Halloween

Eat at Horsefeathers

Horsefeathers Restaurant | Where to Eat in Sleepy Hollow | Halloween in Sleepy Hollow Country | The Best Things to Do in Sleepy Hollow | The Legend of Sleepy Hollow | Sleepy Hollow Travel Guide | Tarrytown, New York | Westchester County New York Halloween Activities Near New York City | Headless Horse | Cemetery Tours | The Great Jack O Lantern Blaze | Hudson Valley Halloween

  • While it technically isn’t one of the many historic sites in the area, if you’re visiting Sleepy Hollow during the Halloween Season (or really any time of year) you MUST eat at Horsefeathers .
  • Since opening its doors in 1981, Horsefeathers has been a staple in the Westchester restaurant scene.
  • Horsefeathers’ decor year round pays homage to all the spooky Sleepy Hollow fictional and non-fictional greats, like the Headless Horseman, Washington Irving, Ichabod Crane and more, but owner Julia McCue really goes all out for the month of October when it comes to Halloween decorations.
  • From November to September Horsefeathers takes reservations, but during October it’s walk in only.
  • Open Tuesday through Sunday for Lunch & Dinner. Saturday and Sunday they serve brunch until 2:30pm.
  • 94 N Broadway, Tarrytown, NY 10591

bookshelf

Visit Old Dutch Church & Burying Ground

  • Founded in 1685, the Old Dutch Church of Sleepy Hollow or Dutch Reformed Church is the oldest extant church in New York.
  • It is featured prominently in “The Legend of Sleepy Hollow” and the burying ground is the alleged haunt of the headless horseman and resting place of local citizens who inspired Irving’s characters of Katrina Van Tassel, Brom Bones and more.
  • It was designated a National Historic Landmark in 1961.
  • Reminder: This is an active congregation, please be respectful of worship services, weddings and funerals.
  • 430 North Broadway, Sleepy Hollow, NY 10591
  • No parking on site. You must park inside the adjacent Sleepy Hollow Cemetery and walk.

Headless Horseman Bridge

  • While the Headless Horseman Bridge, where the Headless Horseman hurls a pumpkin at Ichabod Crane, is one of the most sought after destinations during Halloween in Sleepy Hollow Country, it actually doesn’t exist (at least not anymore)!
  • There is a rustic wooden bridge in the Cemetery that many consider the Headless Horse Bridge (and is DEFINITELY worth visiting), but its a little upstream from where the Post Road bridge stood in Irving’s time. (If you want to visit it’s just inside the cemetery’s south gate)
  • There’s also a sign and bridge plaque that marks the spot of the alleged original bridge near the Old Dutch Church on a modern, concrete bridge that stretches over the Pocantico River. This is also where the statue of the Headless Horseman is located (near 362 Broadway).

four women in a dark costume

Philipsburg Manor

  • The 18th century plantation turned museum that includes the large stone manor house and grist mill on the banks of the Pocantico River that was home to 23 enslaved individuals. While touring the house you’ll learn about the Philipse family and the enslaved community.
  • Visit here to participate in hands-on activities of the 18th century and learn the riveting yet little-known story of enslavement in the colonial north.
  • Tours run from May 6-November 13th, Friday-Sunday between 10:30am & 3:30pm.
  • Advanced Tickets required.
  • Family friendly!
  • 381 N. Broadway, Sleepy Hollow, NY 10591

Tarrytown Halloween Parade

  • The 20th annual Village of Tarrytown Halloween Parade is taking place on Saturday, October 29th . It starts at 5:30pm at Patriot’s Park and runs down Broadway to Tarrytown’s Main Street .
  • Block party to follow on Main Street with a DJ and live music, outdoor dining, performers and much more!
  • Viewing along the parade route is FREE!
  • You can participate by marching in the parade with a theme as a group or float for a chance to win prizes! Registration is required ahead of time.

Washington Irving’s Sunnyside House

  • Nestled along the banks of the Hudson River, the Landscape of Washington Irving’s Sunnyside has been charming guests for generations.
  • Visitors learn about Washington Irving’s storied past and how he came to be America’s first internationally famous author. Best remembered now for The Legend of Sleepy Hollow, his characters from Brom Bones and Ichabod Crane to the Headless Horseman and the Rip Van Winkle, are American culture icons.
  • From May 6-September 11 (Fridays-Sundays between 10am & 3:30pm), tours of Sunnyside are available.
  • From September 16-November 13 (Fridays-Sundays, plus Columbus & Halloween) Sunnyside Home of the ‘Legend’ Tours are available. This differs from the above tour because they decorate the house for the season, there are games on the lawn and it highlights how the ‘Legend’ has lived in the imagination of popular culture for centuries.
  • Parking available onsite.
  • 3 W Sunnyside Lane, Irvington, NY 10533

See Irving’s ‘Legend’ Performance

  • “The Legend of Sleepy Hollow”, one of America’s first ghost stories, as you’ve never heard it before.
  • Performed outdoors under the stars at Washington Irving’s Sunnyside, master storyteller Jonathan Kruk delivers a dramatic performance of the classic tale.
  • Runs Fridays-Sundays plus Columbus Day & Halloween from September 30th – October 31st!
  • Advance Tickets required.
  • Includes live music and an appearance from the Headless Horseman himself!
  • Great for all ages!
  • This experience is outdoors and requires walking!

Haunted Hayride

  • Follow Ichabod Crane’s flight path from the Headless Horseman down Albany Post Road past the Old Dutch Church on Sleepy Hollow’s annual Haunted Hayride.
  • Stay entertained before and after your hair-raising ride at the Sleepy Hollow Block Party.
  • Advanced tickets required.
  • Sleepy Hollow Village Hall, 28 Beekman Ave, Sleepy Hollow, NY 10591

Sleepy Hollow Block Party

  • Live music, food trucks, vendors and entertainment!
  • The block party will take place on Beekman Avenue in Sleepy Hollow on the same nights that the Haunted Hayrides are running.
  • October 21st & 22nd from 5pm-11pm

Glass Pumpkin Patch

  • Artist, Gregory Tomb, has partnered with the Make-A-Wish Hudson to create a Glass Pumpkin Patch in Kingsland Point Park
  • The festive event will showcase over 1000 whimsical, vibrantly colored handmade glass pumpkins
  • Running October 14-16th from 10am-5pm
  • All proceeds support the Make-A-Wish Hudson Valley.
  • Event is FREE, but there is a fee to park.

Sleepy Hollow Lighthouse

  • Also known as the Tarrytown Light, the Sleepy Hollow Lighthouse is situated just off the riverbank at the southern end of Kingsland Point Park.
  • In 1979, it was listed on the National Register of Historic Places and it is the only lighthouse in Westchester County.
  • Due to preservation and restoration work, the lighthouse itself is closed this season, but you can still view if from the Scenic Hudson RiverWalk.
  • Kingsland Point Park, 299 Palmer Ave. Sleepy Hollow, NY 10591

Rockefeller State Park

  • Donated by the Rockefeller family this park is over 1700 acres and has over 45 miles of carriage trails.
  • If you’re spending Halloween in Sleepy Hollow Country then this is a great place to see the beautiful fall foliage that New York has to offer during October and go hiking, running and picnicking.
  • The park is home to some of Sleepy Hollow folklore like the Spook Rock, Raven Rock and Carl’s Mill.
  • Park is open year round 7am-sunset.
  • Small parking fee to enter.

Hulda’s Night Event

  • Hulda’s Night at Rockefeller State Park Preserve is a step back as you listen to local legends and journey up Old Gory Brook Road Trail and down Witch’s Spring Trail as you near the witch’s home (Hulda’s hut) nearby.
  • Event runs October 19th-22nd & 26th-29th.
  • No children under 10 allowed.
  • Hike is around 2 miles in length with some hills. Bring a flashlight.
  • Park at 25 Sleepy Hollow Rd., Sleepy Hollow, NY 10591

Armour-Stiner (Octagon) House

  • The Armour Stiner House is an octagon-shaped and domed Victorian-style house.
  • It is the only known fully domed octagonal residence and the only house which replicates Donato Bramante’s 1502 Tempietto in Rome.
  • It was designated a National Historic Landmark in 1976.
  • The Octagon House is a private family home and access to the house and the grounds is only available to ticket holders.
  • The Octagon House offers a classic tour from April to December along with many seasonal tours including their Fall/Halloween Tour during the months of September and October.
  • This year, “Myths and Mysteries of The Octagon House” is a tour that focuses on supernatural myths and mysteries about the house.
  • Parking is very limited!
  • Best for ages 12 and up!
  • 45 W Clinton Ave, Irvington, NY 10533

Tarrytown Music Hall

  • The Music Hall was built in 1885 during the Millionaire’s Colony Era when mansions dotted the Hudson Valley landscape and families such as the Rockefellers, Goulds and Vanderbilts gathered at the Music Hall to participate in its lavish balls, flower shows and concerts.
  • Unexplained happenings and paranormal activity have been experienced at Tarrytown Music Hall. Lights mysteriously turn back on after closing, the eerie sound of an unknown singer performing vocal scales in the wings after hours and more. Some artists have ever refused to stay in one particular dressing room because they “sensed a presence”.
  • 2022 Ghost Tours to be announced soon.
  • 13 Main St., Tarrytown, NY 10591
  • Kykuit, The Rockefeller Estate is a majestic paradise with sweeping river views. It was home to John D. Rockefeller, founder of Standard Oil, the richest man in America at his time and not it’s a historic site that has been meticulously maintained for more than 100 years.
  • Tours run Saturday & Sunday from May 21st-October 2nd. Wednesday-Monday between October 5th-November 13th.
  • All guided tours start from the Visitor Center at Philipsburg Manor at 381 North Broadway, Sleepy Hollow, NY and include a shuttle bus ride to the estate.

Horseman’s Hollow

  • Unfortunately it’s not running this year, but hopefully it’ll be back next year.

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Sleepy Hollow Cemetery

The original Sleepy Hollow Cemetery

Tours and Events

Tours and events.

Whether you are a history buff, love sculpture, interesting cemetery symbolism, or just want to enjoy the pretty scenery, a visit to historic Sleepy Hollow Cemetery’s 90-acre grounds is a treat. Make the most of your time here by taking one of our guided tours to unlock some of the secrets behind the stones!

Thank you so much for your support during these challenging and unprecedented times. Sleepy Hollow Cemetery Historic Fund is a 501(c)(3) nonprofit organization. All tour proceeds go directly towards preservation and restoration of the grounds. Donations to the Historic Fund are always welcome.

Advance tickets are required. Tickets can be scanned off your mobile phone if you are unable to print them out.

For our special events, CLICK HERE.

For our walking tours, click here..

Sleepy Hollow Cemetery Guided Tours

Photo of Sleepy Hollow Cemetery Guided Tours - Sleepy Hollow, NY, US.

Review Highlights

Roxie D.

“ Also buried there is Washington Irving , who wrote The Legend of Sleepy Hollow and Rip Van Winkle. ” in 3 reviews

Michelle E.

“ I especially enjoyed seeing the coins on Carnegie's tomb as well as Rockefeller 's immense mausoleum. ” in 3 reviews

Ann B.

“ I wanted the Murder and Mehem tour which did not run during the weekdays. ” in 4 reviews

Location & Hours

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Map

540 Broadway

Sleepy Hollow, NY 10591

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Photo of Christina M.

Had some friends in town for the weekend and thought this would be a fun activity. Our tour guide was Christina and she was super friendly, knowledgeable, and passionate about the history of the cemetery (and town!). During the tour, you'll learn stories about people like William Rockefeller, Andrew Carnegie, and of course, Washington Irving, who wrote "The Legend of Sleep Hollow." Though it wasn't part of our tour, the Sleepy Hollow Bridge is located on the cemetery grounds, and you can visit after the tour is over. It's not the original bridge but still nice for a photo op. Based on another review, we tried this trick: if you drive over the bridge slowly, it almost sounds like a horse's hooves. We did a two-hour tour, which is a fair amount of walking, so wear comfy shoes, but there are also one-hour tours. Would also bring sunglasses/a hat and a bottle of water. Because our tour was in April, our group was a bit smaller, but we were told the tours can get pretty packed in the fall, and especially around Halloween. Would definitely recommend checking out (especially if you can do the evening lantern tours!)

sleepy hollow halloween tour

My noble chums and I came to Sleepy Hollow on the Saturday right before Halloween (when else?) to attend The Original Knickerbocker cemetery tour at 11AM. I admittedly did not actively assist in the planning, but the impression I got was that this is a super hot ticket item and that the most popular tours - unsurprisingly, the spooky lantern murdery ones - sell out several months in advance. We were late to the party and ended up here on a gorgeous fall day. If you have your heart set on a lantern tour, having a bright blue sky and fall foliage is a nice plan B. I would caution though that the cemetery is SUPER hilly; we had a pregnant chum who was a little out of breath on some of the inclines. Because of the insane traffic heading into town from the Tappan Zee, which even extended into the cemetery where we had to spend a little time looking for a parking spot, we ended up being 10 to 15 minutes late. That turned out not to be a problem at all, as the tour did not even start until about 11:15am and we were not the last stragglers to show up, presumably for the same congestion-related reasons. Nice to know if you're planning ahead. I spent a ton of time in my childhood on vacations going to historic houses and plantations (very nerdy family), so I've seen my share of tours and tour guides. The best ones are entertaining, informative and quick on their feet. Not every tour goes perfect/according to plan, so if your guide can do some improv, that's a bonus in my view. We had an excellent tour guide. I unfortunately didn't catch her name - it was a woman with darker hair - but she knew her stuff. She dropped a few context clues suggesting that she's been doing these tours for years and it shows. Very in command of the cemetery history overall and had interesting anecdotes to provide based on whatever gravestone or structure we happened to be walking by. At one point, we had to wait a few minutes for a group to finish up at our next official stop. Not a problem - she launched quickly into a tutorial on some of the symbols on the gravestones right in front of us and what they specifically meant about the deceased individuals in question, quite a bit of which was completely new to me (with the exception of the Masonic stuff. Lot of that in the aforementioned nerdy family). We also had to deal with a few accidental tour crashers and one young father who rudely felt the need to take a picture of Washington Irving's grave by stepping in front of the group right next to the guide because he couldn't wait two minutes for everyone to disperse. I honestly don't think there would have been much of a point in getting into a throwdown with that guy (she obviously noticed him though didn't say anything), but the guide was assertive when needed, politely but firmly letting a few people know that it was a paid tour and that they would need to find another way to occupy their time in the graveyard (my words, not hers). At $15, I think you're getting a bargain with the right guide. We had firsthand experience with a pricier option nearby later in the day that didn't hold a candle to this. Is it the greatest tour I've ever been on? Eh. Probably not, but it was a solid good time, and all of us want to come back for the lantern murder festivities next year.

Photo of Jessie P.

Took my family of 4 to Sleepy Hollow for the weekend and we decided to try the American Aristocrat 1 hour guided lantern tour. I'm so glad we did! Amanda, our guide was fantastic. She was knowledgeable, funny, engaging, and clearly enjoyed giving the tours. We learned so many things that we never would have known just wandering around the cemetery ourselves. My 2 kids, ages 14 and 11 both told me that they thought the tour was going to be "lame" but they actually loved it. So did my husband and I! I highly recommend this activity!

Photo of Alicia Lucia 7.

This was such a cool time. It was supposed to rain all day but we realized, it actually made it better. Be sure to put the directions into your gps as the entrance is further up from the main part of town's South Gate. The staff was so professional and courteous. Check in was easy and they start on time. They actually give everyone a real lantern! I thought for some reason they would be giving us small candles or at best, a battery operated one per party. It was so cool. It's optional so if you find them too heavy or cumbersome, you can skip it. Or bring your own lightweight one or a flashlight. The rain added to the atmosphere in my opinion but if you do go in wet weather, boots are a must. We went on both paved and natural surface. There was an initial steep climb up a hill so it's not for the medically frail. In many spots we walked over grass, mud and roots so be very careful. This tour was really better than I thought. The guide told us that the tour is normally two hours but because of COVID, is now one. The stories and beautiful architecture were such a nice treat for this time of year. I'm always up for learning more about Hudson valley history with someone who can make it fun. This place is a non-profit historic site so please enjoy your tour and feel free to donate/tip generously to the care of 90 beautiful acres.

Photo of Jen O.

Dee was our tour guide and was very knowledgeable and enthusiastic. The tour was 2 hours and it def doesn't feel that long and worth it. 100% of the money earned goes to the maintenance of the cemetery which is just an added bonus bc the dates of some of The tomb stones goes back to 1700s and Has some pretty famous residents. Taking the trip to sleepy hollow (especially during the Halloween dates ) is something everyone should experience once . I did take some pictures from The beautiful day but they don't do It any justice from seeing it in person .

sleepy hollow halloween tour

See all photos from Jen O. for Sleepy Hollow Cemetery Guided Tours

Photo of Melinda V.

My BFF from Michigan and her 24yo daughter came out to visit my DH and I and to enjoy the fall beauty. We made reservations online for the Sleepy Hollow Cemetery Lantern Tour. Wasn't sure what to expect or what I'd learn as my DH and I had done the self guided walking tour. So first thing the path is dimly lit with the lanterns and some people on the tour even broke out their cell phone lights. The path is also uneven..some paved..but mainly dirt and rock and grassy. You need to be aware to really watch where you are walking. There are also slight hills. Having said that. It was awesome. Learned a lot about New Yorkers. Rockefeller's, Archibald, Carnegie, Irving and more. Our tour guide was great. Smart and funny, he kept our 30 person group on time without skimping on answering questions. We also got to go into a "Receiving Vault"..the outside of which was in the opening scenes of the old TV show Dark Shadows. Parking is onsite and easy. Even with all that I said regarding the uneven path and hills, my BFF who had a leg brace on and has issues with feeling in one foot found it challenging, but she was able to keep up and both visitors enjoyed it.

sleepy hollow halloween tour

Awesome tour. Great tour guide. Loved the Murder & Mayhem lantern tour. Be prepared to walk. Our tour lasted 1 hr 45 mins; all walking, easy and slow paced. Really cool walking with the lanterns as the evening got dark. One lantern per 2 people. Book online to ensure tickets. I would definitely recommend the tour. Great way to spend a few hours on the weekend.

Tour guide explain tour. One lantern per 2 people.

Tour guide explain tour. One lantern per 2 people.

sleepy hollow halloween tour

We had an amazing tour the other night with the fabulous Row! We took the lantern tour in the evening. It was a two hour tour by lantern light. This tour is the same as the day time tour but it is at night. I'm glad we did this! It was great to learn about the cemetery my family resides in instead of just looking at the building and statues not knowing a thing about them. The atmosphere was fun and not scary at all. Row made sure to tell us that this wasn't a scary tour so if something pops out she would be just as frighted haha. It was just a great experience all around and can't wait to take another tour on our next trip out.

sleepy hollow halloween tour

See all photos from Carleen H. for Sleepy Hollow Cemetery Guided Tours

Photo of Joanne K.

You will NOT be disappointed! I have visited the Sleepy Hollow Cemetery several times and have always left in awe of its natural beauty, the history lessons it teaches, and the art displayed on its gravestones and monuments. Any day you visit is a good one, but on a day in late October or in early November, you will experience the height of fall foliage in the Hudson Valley. It's beautiful, so don't forget to bring a camera. On my visit, I took the guided tour, Murder and Mayhem, to learn the history of the monuments and gravestones and to hear the intriguing stories of the famous and infamous people buried there. My tour guide, Aaron, was friendly, fun, and extremely knowledgeable. He was, and is, a great storyteller. Aaron presented his stories in an engaging and entertaining way as everyone listened intently and wanted to hear more. He fielded questions, provided good direction, and keep the tour on track. It was a great time had by all. I have also been on the Classic Lantern Tour, with Aaron as our guide, which was fun, informative, and an all around great experience as well. So, if you are looking for something to do, visit the Sleepy Hollow Cemetery, admission is free and you will receive a map to help you navigate the cemetery. The rolling grassy hills, majestic trees, and beautiful monuments and grave stones should not be missed. And, if possible, take a tour, it's definitely worth it. There's a lot of walking to do, so, travel light and wear comfortable shoes. I guarantee, you will not be disappointed. Enjoy!

Photo of Danielle J.

Lantern tour was a snooze fest. Our tour guide was so boring and the uphill walking is crazy. Go in the day for free.

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Spooktacular Sleepy Hollow at Halloween Weekend Getaway!

Tarrytown House Estate near Sleepy Hollow New York in the fall

Looking to visit Sleepy Hollow at Halloween time? From September through the end of October, Sleepy Hollow and the villages that surround it in the Hudson Valley in Westchester County, New York attract Halloween and spooky season lovers (like us) to enjoy all the legendary spooky folklore and sites in the area, making this area one of the best places to celebrate fall and Halloween in the world!

Located just 30 minutes north of New York City, we are going to cover how to spend a spooktacular weekend in Sleepy Hollow , New York at Halloween time! Plus, we will include a few other incredible local gems around the Westchester County area on your exciting weekend getaway.

For this weekend getaway, we recommend having a car to explore the area as there are some really cool towns in the Hudson Valley to check out, so you’ll have more flexibility in visiting Sleepy Hollow and attractions in the nearby villages of Tarrytown, Croton-on-Hudson, Dobbs Ferry, Irvington, and Yonkers mentioned in this guide. Plus, the fall foliage this time of year is stunning and taking a scenic drive is a part of the magic this time of year here.

Be sure to see our full guide to all the best things to do in Sleepy Hollow & Tarrytown too!

But, wait! There are so many cool things to do in the Hudson Valley you can read about to also add on to your trip or weekend getaway too!

Disclaimer: This trip was in collaboration with Visit Westchester County, as always all opinions and experiences are our own!

A Brief Background of Sleepy Hollow & Nearby Villages of Westchester County

Historic Philipsburg Manor in Sleepy Hollow New York in fall

Before we dive into how to spend a fun and spooky time during Halloween in Sleepy Hollow, we want to give a brief background and highlights of the area.

Located along the Hudson River north of New York City and Manhattan, for centuries, this area has attracted the wealthiest entrepreneurs from the city offering a countryside escape from the chaos of everyday life in New York City. You’ll find several historic estates and manors in the area with sweeping views of the Hudson River and Palisades including the estates of famed author Washington Irving, whose creative life work has made this a Halloween destination to this day as well as the estate to the Standard Oil tycoon, John D. Rockefeller. 

In addition to the historic estates and luxurious mansions, Westchester is also known for its charming Hudson River villages, beautiful scenery, and historic sites.

Because we are focusing on the fall and Halloween season festivities, the focal point of this guide will be Sleepy Hollow because it’s the most well-known and famous village in the area, although we will be showcasing nearby sites as well as everything is pretty close to one another and with a car, you won’t be driving more than 20 minutes in between sites at the most.

Sleepy Hollow is famous for its haunting atmosphere, largely thanks to the imagination of Washington Irving, often referred to as the ‘father of American Literature’ who published a series of short stories including, The Legend of Sleepy Hollow and Rip Van Winkle , two of the most well-known short stories and his work would go on to inspire other famed authors like Nathaniel Hawthorne, Herman Melville, and Edgar Allan Poe to name a few.

Irving grew up in Manhattan but built his countryside estate here in Tarrytown, featured later on in this guide, and is buried in the Sleepy Hollow Cemetery where the legendary tale of Ichabod Crane and the Headless Horseman took place, what’s considered the first ghost story in American literature. 

The area and its locals embrace the spooky folklore and legacy here and go above and beyond for the Halloween season! From Halloween decor, haunted sites, a chance to walk through thousands of blazing pumpkins, ghost stories, and more – Sleepy Hollow and Tarrytown have maintained their legendary status around this time of year being truly one of the best places to celebrate Halloween in the world!

So without further ado, here are some of the incredible activities to fill your Halloween in Sleepy Hollow weekend getaway! Be sure to see our guide to the best things to do in Sleepy Hollow and Tarrytown for more ideas of things to include on your trip.

Weekend in Sleepy Hollow at Halloween (& Nearby Villages)

  • Visit Sleepy Hollow

Downtown Sleepy Hollow New York on Beekman Avenue in Westchester County

If you’re visiting Sleepy Hollow at Halloween, you need to take a stroll downtown, a few of the things mentioned in this weekend guide to the area include a few landmarks in Sleepy Hollow as well. We suggest starting at Beekman Avenue by Broadway where you can enter the ‘downtown area’ of Sleepy Hollow. During Halloween time you’ll spot spooky decor at the Sleepy Hollow clock.

Take a stroll down Beekman to browse the stores, shops, restaurants, and spooky decor downtown! If you’re visiting in the morning, we had a great bagel at Headless Bagel (next to Carvel) or if you’re visiting around lunch/dinner pay a visit to Beekman Ale House for a meal and drink, which was also decorated with spooky decor.

From here, you can walk to historic and popular sites like Sleepy Hollow Cemetery and Phillipsburg Manor as well in under 5 minutes. 

You can walk down to the waterfront and enjoy the trail and views along the Hudson River as well as visit the Sleepy Hollow Lighthouse.

  • Sleepy Hollow Cemetery & Old Dutch Reformed Church

The Old Dutch Reformed Church in Sleepy Hollow

Address: 540 N Broadway, Sleepy Hollow

An iconic place to visit in Sleepy Hollow at Halloween is the Sleepy Hollow Cemetery and Old Dutch Reformed Church, which plays a pivotal role in the setting of Washington Irving’s, The Legend of Sleepy Hollow . 

While the Old Dutch Reformed Church has its own burying ground in the churchyard and the Sleepy Hollow Cemetery are technically two different sites, they are easy to combine together as you can easily access one from the other.

The Old Dutch Reformed Church, also known as The Old Dutch Chruch of Sleepy Hollow, is a 17th-century stone church and was in Irving’s 1820 legendary tale which is also one of the oldest buildings in the state! Irving used the cemetery not only as the location where the Headless Horseman would start his nightly ride in his short story, but he also used the names from some of the gravesites here for his characters including Brom Bones and Katrina Van Tassel, whose gravestones you can visit.

After visiting the old churchyard, you can visit the gravesite of Washington Irving, which is technically a part of the Sleepy Hollow Cemetery. There are signs that will lead you to his family plot and gravesite which is helpful and makes it easy to find.

Other notable figures buried in Sleepy Hollow Cemetery include figures throughout American history like William Rockefeller, Andrew Carnegie, and Walter Chrysler to name a few. The cemetery itself is pretty large, so after visiting the sites around the Old Dutch Reformed Church, if your car is nearby you can explore the rest by driving through the cemetery (unless you’re up for a walk).

pretty wooden bridge over the Pocantico River in Sleepy Hollow Cemetery in New York

Be sure to check out the beautiful wooden bridges over the Pocantico River, which resemble what perhaps Irving imagined being the bridge in his short story, as the actual site of the Headless Horseman Bridge (marked with a sign) on Broadway is a more modern bridge that can handle automobile traffic and not reflective of what perhaps the area looked like when Iriving was inspired by in the 1800s. 

The graveyard is open to the public from 8:00 AM to 4:30 PM so be sure to plan your visit around these hours.

  • Explore Tarrytown

Tarrytown Music Hall in the Hudson Valley New York

Neighboring Sleepy Hollow is Tarrytown, which are less than a mile a part from one another. The Village of Tarrytown is charming and much like Sleepy Hollow at Halloween, the area has all kinds of spooky decor and you’ll spot several nods to the Headless Horseman and Irving’s characters from his classic tale.

Be sure to take a lap down Main Street (off of Broadway) where you can find plenty of opportunities to shop and dine along with catch a show at Tarrytown Music Hall, a historic theater dating back to 1885. They offer shows, ghost tours of the Music Hall with a ‘master storyteller’ and all sorts of programming from plays, performances, and showings of classic films like Rocky Horror Picture Show .

Don’t miss out on some of the cool shops here either like The Swan’s House on Broadway featuring unique home goods combining a curated collection of vintage items and artisan pieces. Speaking of vintage goods, there is also a consignment store and antique store on Main Street worth taking a lap in as well.

If you want to enjoy a walk, make your way down to the Hudson Riverfront and enjoy the views at Pierson Park located right next to the Tarrytown train station.

The Great Jack O’Lantern Blaze

The Great Jack O Lantern Blaze at the Van Cortlant Manor in Croton-on-Hudson New York near Sleepy Hollow in the fall

Address: 525 S Riverside Ave, Croton-On-Hudson

Halloween in Sleepy Hollow is famous, but in recent years The Great Jack O’Lantern Blaze event has become just as famous as the locations directly tied to the Legend of Sleepy Hollow in Irving’s story. Located at the Van Cortlandt Manor in Croton-On-Hudson, around a 20-minute drive north up the Hudson Valley from Sleepy Hollow is a truly remarkable and unique experience (welcoming of all ages) that you won’t want to miss during the Halloween season!

Blaze, as locals call it, is an immersive walk through over 7,000 hand-carved, illuminated jack o’lanterns! There are several different displays and art installations all made with these blazing pumpkins including a jack o’lantern constellation tunnel, the Headless Horseman and Ichabod, NYC landmarks recreated as pumpkins like the Statue of Liberty, and more all on the grounds of a historic 18th-century manor (that’s also decked out in Halloween decorations with a light show synched to music).

This event is so popular they now have a location in Long Island too. The season to get tickets starts typically in mid-September and ends in November. You’ll need to reserve your tickets in advance , this is a hot item so you won’t want to miss out either, we advise booking your tickets as soon as you know the dates of your trip because they do sell out.

Visit Washington Irving’s Sunnyside Estate

Washington Irving's Sunnyside estate on the Hudson River in Irvington New York near Sleepy Hollow

Address: 3 W Sunnyside Ln, Irvington

Located in Irvington, New York (around a 10-minute drive from Sleepy Hollow) is the home of the legend himself, Washington Irving. His estate, known as Sunnyside, was where he built his countryside home near where he spent his childhood escaping the Yellow Fever Outbreak in New York City. His youthful years in the area would go on to inspire the setting in his short story, The Legend of Sleepy Hollow which he wrote while in England.

When Iriving returned stateside after becoming the first internationally celebrated American author, he built his dream countryside home here right along the Hudson River where visitors can see the creeping wisteria vines on the house that Irving planted himself over 200 years ago and retrace the footsteps of the father of American Literature.

During the months of September through November, visitors are able to tour the ‘Home of the Legend’  including the grounds surrounding his home and a tour inside the rooms on the first floor of his home. On the weekends during the month of October, visitors can enjoy Irving’s Legend performance in the evenings where a local master storyteller puts on a live-action performance of the story at the estate at dark for an audience.

For both of these events, you’ll need to book your tickets in advance as they do not sell them on-site.

  • Tour the Armour-Stiner Octagon House

The Armour Stinner Octagon House in Tarrytown New York

Address: 45 W Clinton Ave, Irvington

Another not to be missed attraction near Sleepy Hollow at Halloween time is touring the unique and pin Armour-Stiner Octagon House in Irvington. 

This unique octagon-shaped home was built by Paul J. Armour in the 1860s and was inspired by the octagonal homes that were a popular style in the pre-Civil war era. The home changed ownership in 1872 to Joesph Stiner, hence the name Armour Stiner and added the gorgeous dome that is said to be inspired by Donato Bramante’s 1502 Tempietto in Rome.

inside the greenhouse at the pink Armour-Stiner Octagon House in Irvington New York

There are actually tours available throughout the year, but during the months of September through October concentrate on themes surrounding the mysteries and said paranormal activity in this home on their “Myths and Mysteries of The Octagon House” tour . Which is perfectly on theme for a spooktacular weekend getaway in Sleepy Hollow at Halloween time.

While the house does offer tours, it is a private residence and you are only able to visit by a guided tour booked in advance. The owner of the home, Joesph Pell Lombardi, is responsible for the restoration of the home to its 1872 appearance and furnishings. Lombardi is a world-renowned and famous real estate investor and preservationist who’s won awards and accolades for his preservation work including a 12th-century chateau in France.

Before or after your tour you can take a walk around the veranda or property to check out the matching pink carriage house (where his son/preservation partner resides) and greenhouse.

  • Check Out Kykuit Rockefeller Estate

Kykuit the Rockefeller Estate overlooking the Hudson Valley in New York in the fall

Address: 381 N Broadway, Sleepy Hollow (meeting location for tour)

Located in the Pocantico Hills above Tarrytown and Sleepy Hollow with sweeping views of the Hudson River and Valley is one of the most prestigious and historic estates in Westchester County. Kykuit, also known as the John D. Rockefeller Estate, was home to one of the wealthiest men in American history.

In 1913, John D. Rockefeller, the famous oil tycoon of Standard Oil, had the vision to build a grand countryside estate. Four generations of Rockefellers lived in this estate, which serves as a museum to the public with an impressive art collection on display for visitors on tours as well as beautiful gardens.

the fountain at Kykuit the Rockefeller Estate near Sleepy Hollow in the Hudson Valley New York

John D. Rockefeller’s grandson, Nelson Rockefeller (former Governor of New York and Vice President of the United States) curated and collected one of the greatest private collections of modern art in the country on the property including works from artists like Warhol to Picasso and are located in a private underground, basement gallery in addition to outdoor sculptures around the gardens.

To visit Kykuit (available May – November) you will need to purchase tour tickets in advance . There are three tour options ranging from one hour to three hours. Once you have your tickets, you will meet at the Phillipsburg Manor in Sleepy Hollow at the visitors center to check-in. They will provide a private shuttle up to the estate and return you back down here after your tour.

  • Stop by the Union Church at Pocantico Hills

The Rose Window during the daytime by Henri Matisse at The Union Church of Pocantico Hills in the Hudson Valley New York

Address: 555 Bedford Rd, Tarrytown

Another Rockefeller artistic contribution to the area can be found at the Union Church of the Pocantico Hills, right near the entrance to Kykuit. If you’re visiting Sleepy Hollow around Halloween, this area is especially beautiful to drive to as the fall foliage is a sight to see.

Commissioned under Nelson Rockefeller as a memorial for his mother, the church is home to one of Henri Matisse’s last completed commissioned works in his lifetime, the Rose Window accompanied by nine stained glass windows by Marc Chagall.

Keep in mind this is an operating church, you’ll need to join a tour to visit and no photography is permitted inside the church. Tours are available on select dates (typically weekends) from May through November and you’ll want to purchase your tickets in advance.

If you can’t get your hand on tickets, you can drive past the church and see the Rose Window from the exterior of the church.

  • Spend Time at Croton Gorge Park

New Croton Dam waterfall at Croton Gorge Park in the Hudson Valley New York

Address: 35 Yorktown Rd, Croton-On-Hudson

If you’re visiting Sleepy Hollow by car, we highly encourage you to explore a little. Before visiting The Great Jack O’Lantern Blaze in Croton-On-Hudson, we recommend stopping by Croton Gorge Park where you can take a walk around the base of the New Croton Dam and the pretty man-made waterfall here.

There are trails and areas to picnic too, but we came mostly for the views. The New Croton Dam is impressive as when it was completed in 1906, it was considered the tallest dam in the world. The waterfall here is picturesque and a fun stop to check out in the area.

Visit Rockefeller State Park Preserve 

Tarrytown Lakes Park at the Resevoir in Tarrytown New York

Address: 125 Phelps Way, Pleasantville

Visiting Sleepy Hollow at Halloween means you’ll be visiting around all the beautiful fall foliage. If you’re looking for outdoor activities to enjoy or a place to enjoy a nice leisurely hike, visit the Rockefeller State Park Preserve in Mount Pleasant, nearby Sleepy Hollow, and the Pocantico Hills.

The park was a part of the Rockefeller estate and was donated to the State of New York in 1983 for the public to enjoy, although the Rockefellers were welcoming of the public using the land as a park as early as the 1970s.

There are several trails spanning 45 miles to enjoy  on the original crushed stone carriage roads that John D. Rockefeller and his son laid out themselves in the early 20th century, which are wide and easy to walk on not to mention there are wood and stone bridges crossing the Pocantico River and other streams as well as beautiful rock outcroppings, Swan Lake, and beautiful forest scenery to enjoy.

There are several easy trails to hike . You can park at the Rockefeller State Park Preserve parking lot ($6 per car at the pay machines).

  • Wander Around Untermyer Gardens Conservancy

Temple of Love at Untermyer Gardens Conservancy in Yonkers New York

Address: 945 N Broadway, Yonkers

Located in Yonkers in Westchester County, this is a great stop if you’re heading back to New York City after your weekend in Sleepy Hollow. Located along the Hudson River at the former site of the estate “Greystone,” are the grand gardens added to the now-demolished estate by Samuel Untermyer.

Untermyer Gardens Conservancy is now a public park, donated by Samuel Untermyer, hence the name. The gardens were a part of his vision for his countryside estate that he purchased, located on a steep parcel of land overlooking the Hudson River and New Jersey Palisades. 

Untermyer was a successful corporate lawyer in New York City turned civic leader, he wanted to build a grand garden that rivaled the gardens found at Kykuit, the Rockefeller estate nearby. At the time of their construction, the garden was considered one of the finest in the country.

Gorgeous view at Untermyer Gardens Conservancy in Yonkers Westchester County New York

The park is completely free to visit and a must if you’re in the area. Some of the features of the beautifully restored park include the Temple of Love, a rock and water garden with cascading waterfalls and a majestic view from the top, the Walled Garden which was designed and inspired by Indo-Persian gardens, and the long staircase from the Walled Garden to the Overlook with incredible views of the Hudson River.

Where to Eat in Sleepy Hollow at Halloween Time

Goosefeather.

Kung Pao Fried Chicken and Mochi Waffles at Goosefeather restaurant at Tarrytown Estate in New York

Address: 49 E Sunnyside Ln, Tarrytown

Not to be missed during your weekend in Sleepy Hollow is the weekend brunch available at Goosefeather, a Cantonese restaurant located in the 1840s historic property at Tarrytown House Estate on Hudson, also a hotel in the area. 

James Beard nominated Chef Dale brings the flavors of Hong Kong here to the Hudson Valley with an innovative menu that even has nods from Michelin. Chef Dale also has made several television appearances including Top Chef, Chopped, Knife Fight, Beat Bobby Flay, and is the host of Tastemade’s All Up in My Grill.

In addition to great Cantonese-inspired dishes, there are several incredible brunch items to try, we highly recommend trying the Kung Pao Chicken and Mochi Waffles along with dumplings from their smaller plate options. We were also impressed with the Roasted Mushroom and Coconut Grits, which was a perfect combination of savory and sweet combining the flavors of umami butter, pomegranate seeds, and a six-minute egg along with the mushrooms and coconut grits. It was definitely not something we try to do at home, but Chef Dale has really created a stand-out dish with these flavors complimenting each other beautifully.

In addition to an impressive brunch menu, Goosefeather is open for dinner. Also, the space is absolutely beautiful too.

Brunch is available on the weekends starting at 11 AM, you’ll want to make a reservation.

Horsefeathers

Horsefeathers in Tarrytown New York at Halloween

94 N Broadway, Tarrytown

Located in the heart of Tarrytown is one of the best stops for lunch or dinner during the season of Halloween in Sleepy Hollow. Horsefeathers has an old tavern ambiance and is decked out with Halloween decor including a nice list of pumpkin beers, ales, ciders, and other fun ‘spooky’ drinks to add to your spooktacular weekend in Sleepy Hollow.

They serve up classic American pub fare, we highly recommend the burgers here paired with a pumpkin-flavored beverage or cocktail of your choice.

This is a very popular spooky season stop because of all of the festive decor and they do not take reservations. We recommend getting here a little early to put your name in as for parties with more than two had a lengthier wait time. We were able to get a seat at the bar without too much of a wait. 

Beekman Ale House

Exterior-of-Beekman-Ale-House-in-dowtown-Sleepy-Hollow-New-York at Halloween

Address: 92 Beekman Ave, Sleepy Hollow

For a great lunch or dinner option in Sleepy Hollow, check out Beekman Ale House, a pub setting with great beer and drinks on draft plus pizza! What we liked about this spot is that it wasn’t too crazy, even during Halloween in Sleepy Hollow and they even have festive decorations.

We stuck with ordering a pizza paired with beer on draft, which was a great choice. They serve up Neopolitan-style pizza with a crispy crust plus a bunch of great shareable options like meatballs and fried mozzarella triangles.

Horseman Bagels

Horseman-Bagels-in-Sleepy-Hollow-during-Halloween-in-the-Hudson-Valley-New-York

Address: 276 N Broadway, Sleepy Hollow

If you’re looking for a quick bite to eat in the morning during your weekend in Sleepy Hollow be sure to visit Horseman Bagels, which shares a space with Carvel, the classic ice cream spot serving up sweet treats.

What’s nice is that this location is directly across from the Sleepy Hollow clock and ‘official welcome’ to the town that’s outfitted with a spooky pumpkin man for Halloween season! You can easily grab a bagel and walk downtown.  right 

EATalia on Hudson

Tagliatalle Bolognese from EATalia on Hudson in New York

Address: 385 S Riverside Ave, Croton-On-Hudson (PERMANENTLY CLOSED AS OF 2023)

If you’re looking for somewhere to grab dinner before heading to Van Cortlandt Manor for The Great Jack O’Lantern Blaze, this is a great stop. Give yourself extra time, this is not a fast-service type of place but their pasta dishes are excellent.

If you order from the specials menu, be sure to ask the price to avoid any confusion on the bill later. We recommend giving yourself at least 75-90 minutes here so you can plan accordingly. Blaze is just up the road and because this is one of the most popular Halloween season attractions, you’ll also want to plan for a small window of time to sit and wait to park in a queue of cars – it wasn’t too long but we gave ourselves ample time to arrive thankfully.

Bread and Brine

exterior of Bread and Brine restaurant in Hastings-On-Hudson in the Hudson Valley New York

Address: 19 Main St, Hastings-On-Hudson

An excellent spot for lunch or dinner in Hastings-On-Hudson, this New England-focused restaurant serves up incredible dishes inspired by the North East Atlantic coast including lobster rolls, a raw bar, and other great dishes like a whole branzino.

Do yourself a favor and after lunch take a lap around Hastings-On-Hudson, there are a few cute shops including a great record store, Clockwork Records and a cute antique shop on the corner of Main and Warburton, Suburban Renewal. 

Drive (or walk) down to MacEachron Waterfront Park for waterfront views and you can also see the skyline in the distance down the Hudson River.

Where to Stay During Your Sleepy Hollow Halloween Weekend: Tarrytown House Estate

aerial view of Tarrytown House Estate in Tarrytown New York in the Hudson Valley

For your weekend in Sleepy Hollow at Halloween, one of the best options for lodging and where to stay are the historic grounds of the Tarrytown House Estate . A popular wedding venue too, this hotel is situated on 26-acres with gorgeous 19th-century mansions including the Carriage House and Cottage, Biddle Mansion, and King Mansion.

The King Mansion is also the location of Goosefeather restaurant, which is a must during your Sleepy Hollow weekend trip. In addition to being a gorgeous property, the location is also excellent as you’re just a short drive to both Tarrytown and Sleepy Hollow making it a really great base for exploring all the stops in Westchester County featured in this guide.

The hotel rooms are inside a contemporary building between the historic properties. Enjoy your morning coffee walking around the property or cozy up by the firepits in the evening. There is an outdoor pool and indoor pool, sauna, racquetball, and tennis courts.

The property is really beautiful and reminded us of our stay in a historic property in Ireland . For the season of Halloween in Sleepy Hollow you’ll want to secure your reservation in advance, especially on the weekends as many weddings use the property as a venue and the rooms can book up quickly. Book here.

Getting to Sleepy Hollow & Westchester

view of the NYC skyline from the Hastings-On-Hudson waterfront in Westchester County New York

Getting to Sleepy Hollow (and the nearby villages) from New York City couldn’t be easier as the Metro-North Railroad Hudson Line has several stops along the Hudson Valley including an express service between Grand Central Terminal in NYC and Tarrytown (which takes around 35-min).

You can easily take the train from many stops included on this weekend getaway to the Sleepy Hollow area including stops at Hastings-On-Hudson, Tarrytown, Sleepy Hollow, and Croton-On-Hudson, you will just need to plan your schedule to the train time tables .

From Penn Station, you can also use the Amtrak train to get to Metro-North’s Croton-Harmon Station.

Also, some of the local hotels have a shuttle service they offer to and from the train station making it possible to do this trip without a car if you don’t have one or don’t want to rent a car.

We prefer renting a car or driving so you have more flexibility, not to mention the drives here around fall are stunning because of the fall foliage.

You also have the option for taking the train up to Tarrytown or flying into Westchester County Airport (HPN) in White Plains and then renting a car once you’re here. There are even rental car options in Tarrytown and you can also use Zipcar in the area.

Tips for Visiting Sleepy Hollow at Halloween

The pumpkin bridge at The Great Jack O'Lantern Blaze at Croton On Hudson in Westchester New York near Sleepy Hollow

Halloween time at Sleepy Hollow and the surrounding areas is the most popular time to visit. There are so many Halloween-focused attractions plus the North East is popular this time of year for leaf peepers. 

With that in mind here are a few tips to make sure you’re prepared:

  • Parking can be competitive in the villages, have quarters on you for parking meters (they also have options to pay online) and be prepared that you may have to circle the downtown areas during peak times to find a spot. Or park a little further away and walk into where you’re going.
  • Be sure to check any restaurants that you want to visit for reservations. Not all, like Horsefeathers, takes reservations in advance. If you’re visiting on the weekend and you didn’t get a reservation, schedule time in to wait for a table.
  • Most attractions in the area require advance tickets and reservations. Be sure to look up all attractions you want to visit to secure your tickets in advance, especially for popular spots like The Great Jack O’Lantern Blaze, Washington Irving’s Sunnyside, and Kykuit. These places will not let you buy tickets on-site and often sell out.

Things to do in Sleepy Hollow at Halloween (Post Summary):

  • The Great Jack O’Lantern Blaze
  • Visit Washington Irving’s Sunnyside Estate
  • Visit Rockefeller State Park Preserve
  • Have Brunch at Goosefeather
  • Have a Meal at Horsefeathers
  • Stop at Beekman Ale House for a Meal
  • Have a Bagel from Horseman Bagels
  • Dinner at EATalia on Hudson
  • Enjoy Lunch at Bread and Brine

No, you do not need tickets to visit Sleepy Hollow as it’s a town, but if you are hoping to do specific attractions or tours those may require tickets.

Yes, Sleepy Hollow, NY is worth visiting for its historical charm, ties to Washington Irving’s “The Legend of Sleepy Hollow,” scenic Hudson River views, and seasonal events like Halloween festivities.

Sleepy Hollow, NY celebrates Halloween with the Great Jack O’Lantern Blaze, an elaborate display of thousands of intricately carved pumpkins, creating a mesmerizing and magical experience for visitors.

Yes, Sleepy Hollow is worth visiting during Halloween for its renowned Great Jack O’Lantern Blaze nearby and spooky ambiance, plus the town is decorated for Halloween!

Enjoyed this guide to how to spend a spooktacular weekend in Sleepy Hollow at Halloween? Bookmark for later or share the love below on Pinterest!

For more spooky season destinations check out our guide to all the best things to do in Salem , which is not too far of a journey away and also check out our favorite places to visit in New York in fall !

sleepy-hollow-new-york-weekend-getaway

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Home of the 'Legend'

Explore “the legend of sleepy hollow”.

At this family-friendly happening, visitors can tour Washington Irving’s house—decorated for the season—watch an original shadow puppet short film, and enjoy games on the lawn. A special exhibit highlights how the Legend has lived in the imagination of popular culture through the centuries since its publication.

Select Dates Sep 15-Nov 12

Fridays – Sundays + Columbus Day, October 30, and Halloween

Advance tickets required. 

Adult: $12 Senior (65+): $10 Student (18-25): $10 Child (3-17): $10 Members: 15% discount off of regular ticket price Children under 3:  FREE

$2.50/ticket surcharge for phone purchase

Tickets are exchangeable to another date/time slot if that date/time has availability, up to 72 hours in advance of your reserved time slot. There is a $2.50 per ticket exchange fee. Please see Historic Hudson Valley’s Ticket Refund and Exchange Policy  for more details.

Washington Irving’s Sunnyside GPS address: 3 W Sunnyside Lane, Irvington, NY 10533

Is photography allowed?

Photography and video recording for personal use are permitted on the grounds. No photography of any kind is permitted inside the house. Audio recording of the tours is also not permitted.

What's your weather policy?

Home of the ‘Legend’ is held rain or shine. If you elect not to attend, your tickets are neither refundable nor exchangeable. In poor weather, ticket holders should consult local weather forecasts for their own area and make their own determination about whether to set out for the evening’s event.

An event may be canceled by Historic Hudson Valley if, in its sole judgment, extreme weather or other conditions could jeopardize the safety of visitors, volunteers, and staff. Generally, rain, snow flurries, or showers would not lead us to cancel, but extremely heavy rain, thunder, and lightning, very strong wind; blizzard conditions, heavy icing, or a prediction of such conditions could force us to do so. If Historic Hudson Valley determines that conditions warrant canceling an event, we will post a message on our website and voicemail and ask local radio stations to make an announcement.

Is the site wheelchair accessible?

Visitor Center and Site Access

  • Handicapped parking is available and handicapped restrooms are available in the Visitor Center.
  • The walk from the parking lot to the Visitor Center is approximately 379 feet down a graded wheelchair accessible ramp.
  • The walk from the Visitor Center to the Cottage is approximately 570 feet on a graded decline, much of which is on a wide pebble path. From the courtyard of the Cottage back to the Visitor’s Center is approximately 380 feet on a graded incline.

Historic Core and Irving’s Cottage

  • The grounds and the first floor of the Cottage are wheelchair accessible.
  • There is a narrow, steep flight of stairs (12-15 steps) to the second floor of the house and another steep and winding flight of stairs from the second floor to the kitchen.

Are there nearby dining options?

There are also many excellent dining options in the area. Find a restaurant now.

Are tickets refundable?

Tickets are exchangeable to another date/time slot if that date/time has availability, up to 24 hours in advance of your reserved time slot. There is a $2.50 per ticket exchange fee. Please see Historic Hudson Valley’s Ticket Refund and Exchange Policy for more details.

Are pets permitted at Sunnyside?

Pets are not allowed at Sunnyside. Service dogs are welcome.

Related learn more

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Significant Collection Related to Washington Irving Joins Our Collection

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Restoring a 19th-Century Bandbox and Preserving Washington Irving’s Uniforms

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Together Again: Washington Irving and Thomas Storrow Portraits at Sunnyside

Legend of Sleepy Hollow Shadow Puppet Film

Digital Experiences Mark Bicentennial of Washington Irving’s Stories

One of a set of six drawings to illustrate

The Great American Ghost Story: The Legend of Sleepy Hollow

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Will it be easy to find my way in the Moscow Metro? It is a question many visitors ask themselves before hitting the streets of the Russian capital. As metro is the main means of transport in Moscow – fast, reliable and safe – having some skills in using it will help make your visit more successful and smooth. On top of this, it is the most beautiful metro in the world !

. There are over 220 stations and 15 lines in the Moscow Metro. It is open from 6 am to 1 am. Trains come very frequently: during the rush hour you won't wait for more than 90 seconds! Distances between stations are quite long – 1,5 to 2 or even 3 kilometers. Metro runs inside the city borders only. To get to the airport you will need to take an onground train - Aeroexpress.

RATES AND TICKETS

Paper ticket A fee is fixed and does not depend on how far you go. There are tickets for a number of trips: 1, 2 or 60 trips; or for a number of days: 1, 3 days or a month. Your trips are recorded on a paper ticket. Ifyou buy a ticket for several trips you can share it with your traveling partner passing it from one to the other at the turnstile.

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On every station there is cashier and machines (you can switch it to English). Cards and cash are accepted. 1 trip - 55 RUB 2 trips - 110 RUB

Tickets for 60 trips and day passes are available only at the cashier's.

60 rides - 1900 RUB

1 day - 230 RUB 3 days - 438 RUB 30 days - 2170 RUB.

The cheapest way to travel is buying Troyka card . It is a plastic card you can top up for any amount at the machine or at the ticket office. With it every trip costs 38 RUB in the metro and 21 RUB in a bus. You can get the card in any ticket office. Be prepared to leave a deposit of 50 RUB. You can get it back returning the card to the cashier.

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SamsungPay, ApplePay and PayPass cards.

One turnstile at every station accept PayPass and payments with phones. It has a sticker with the logos and located next to the security's cabin.

GETTING ORIENTED

At the platfrom you will see one of these signs.

It indicates the line you are at now (line 6), shows the direction train run and the final stations. Numbers below there are of those lines you can change from this line.

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In trains, stations are announced in Russian and English. In newer trains there are also visual indication of there you are on the line.

To change lines look for these signs. This one shows the way to line 2.

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There are also signs on the platfrom. They will help you to havigate yourself. (To the lines 3 and 5 in this case). 

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Visit Sleepy Hollow

Where the Legend Lives

  • Christ Episcopal Church
  • David Rockefeller Creative Arts Center at Pocantico
  • Headless Horseman Bridge
  • Headless Horseman Statue
  • Historical Society
  • Legend Landmarks

Spring Crafts at Lyndhurst

  • Octagon House
  • Old Croton Aqueduct Trail
  • Old Dutch Church
  • The Pinkster Festival
  • Rockefeller State Park Preserve 

Cemetery Song

  • Sleepy Hollow Cemetery Tours
  • Sleepy Hollow Lighthouse
  • Union Church of Pocantico Hills
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Tarrytown Street Fair

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Three pumpkins nestled in fallen leaves in Sleepy Hollow Cemetery.

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Calendar of Events

4 events, 28, irvington farmers market.

Enjoy live music, river views and a laid-back setting at this small-town Sunday market showcasing the best of what the Hudson Valley has to offer. In season, there is fresh local produce, seafood and meats, cheese, pickles, prepared foods and baked goods. The market is just a short distance from Washington Irving’s home Sunnyside. Look …

The Original Knickerbocker Tour

The Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about Washington Irving, his impact on American Literature and the enduring appeal of “The Legend of Sleepy Hollow”, which recently celebrated its Bicentennial. Best of all, …

Classic Daytime Cemetery Tour

Soak up the beauty of this 175-year old cemetery while your guide regales you with stories of the fascinating people resting here in peace. This two-hour daytime walk is the perfect way "to have a colloquy among the tombs" as Washington Irving, famous author of "The Legend of Sleepy Hollow", did himself back in 1849. You'll …

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0 events, 30, 0 events, 1, rickie lee jones.

Rickie Lee Jones is an American musician, storyteller and two-time Grammy winner who has been inspiring pop culture for decades, beginning with her star-making self-titled debut, followed by the seminal Pirates. Named the “premiere song-stylist and songwriter of her generation” by The New Yorker, and “The Duchess of Coolsville” by Time magazine, Jones released her …

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The Spring Craft Show by ArtRider at Lyndhurst returns from May 5th through May 7th with 200 craftspeople and makers! Shop for one-of-a-kind gifts for Mother’s Day, Father’s Day, graduations, weddings, or just for yourself! Visitors can spend the day with family and friends shopping for original fashions, accessories, jewelry, home décor, furniture, photography, and …

Kykuit Tours

A majestic paradise with sweeping river views. See the Hudson Valley’s top cultural attraction! Built between 1906 and 1913, Kykuit was home to four generations of the Rockefeller family, beginning with the philanthropist John D. Rockefeller, founder of Standard Oil. His business acumen made him, in his day, the richest man in America. Now a …

Kevin Nealon

Kevin Nealon is an Emmy and SAG-nominated actor and comedian who sets himself apart from other comedic performers with his unique sense of humor, dry wit and likable demeanor. Nealon is best known for his nine-year stint as a cast member of NBC’s Saturday Night Live, and received critical acclaim for his role in the …

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6 events, 5, 0 events, 6, 0 events, 7, 0 events, 8, rodrigo y gabriela.

Grammy Award winning duo Rodrigo y Gabriela grew up on an eclectic mix of classic rock, heavymetal and flamenco, a rare alchemy of influences that still informs their work today. Not long after the dissolution of their first band, the two musicians set off with their acoustic guitars and ended up in Ireland, where they …

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Three figures stand in the lamplit darkness, their voices rising: an old woman, bent but strong and steel-eyed; a woman in the prime of life – a leader, a creator, a mother; and a young girl, full of curiosity and intelligence. Their song is haunting but joyful. As they sing, others begin to emerge from …

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5 events, 12, 0 events, 13, 0 events, 14, 0 events, 15, 1 event, 16, krishna das benefit concert for tibetan home of hope.

oin Krishna Das and friends for an evening of sacred kirtan music to benefit the Tibetan Home of Hope. The event is co-hosted by the Kirtan Wallah Foundation. Krishna Das is an American vocalist known for his performances of kirtan, a Hindu devotional music. Since 1996 Krishna Das has released sixteen music albums, numerous videos, …

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7 events, 18, sleepy hollow 150th anniversary car show.

This event offers a delightful blend of nostalgia and respect for Sleepy Hollow's automotive heritage, featuring an impressive array of classic vehicles that have left an indelible mark on the village's identity. Alongside classic, antique, and muscle cars, families can enjoy food trucks, music, and a bouncy castle. Rain date: May 19th. Automobile manufacturing was …

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0 events, 20, 0 events, 21, 0 events, 22, 0 events, 23, 2 events, 24, the machine performs pink floyd.

The Machine has forged a 30+ year reputation of extending the musical legacy of Pink Floyd. The New York-based quartet performs a diverse mix of The Floyd's extensive 16-album repertoire, complete with faithful renditions of popular hits as well as obscure gems. With stellar musicianship and passionate delivery, The Machine explores collective improvisation rivaling that …

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Tash farmers market.

Stop by TaSH, Tarrytown’s and Sleepy Hollow’s weekly farmers market, for fresh Hudson Valley produce, meat, bread, cut flowers, dairy products, preserves, wine, and beer. There are weekly live music performances, children’s events as well as ongoing educational activities and programs. Don’t miss the weekly free samplings! Well behaved dogs are welcome, provided your pooch is …

The Pinkster Festival

Join Philipsburg Manor for a day filled with art, poetry, live music, dance, and storytelling that celebrates and commemorates the region’s African American history and culture. Hear a spoken word performance, dance to the beat of African kora, observe an artist in process, participate in a call-and-response song, and more. Brought to the New World …

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1 event, 27, 0 events, 28, 2 events, 31.

A master lyricist and satirical storyteller, John Hiatt delivers songs filled with tales of redemption, relationships and surrendering on his own terms. Hiatt's finest album is 1987's Bring the Family; other catalog highlights include the pop and rock of 1983's Riding with the King, the rough-hewn blues-rock of 2008's Same Old Man, and 2021's Leftover …

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Rockwood ramble 10k.

Starting and finishing in historic Rockwood Hall, the annual Rockwood Ramble 10K is a favorite. Scenic Hudson River views greet runners before the course veers into the woods. The wide carriage roads provide the perfect setting for experienced trail runners and first timers. Say goodbye to traffic, pavement and noise and hello to the Preserve! …

The Sleepy Hollow Tarrytown Chamber of Commerce’s annual Tarrytown Street Fair takes place this year on Sunday, June 4th. Main Street transforms into an outdoor market with food, music, local retailers, arts & crafts, souvenirs and more! Explore more local shopping at Tarrytown's and Sleepy Hollow's galleries, gift shops and antique stores. Rain date: Sunday, June 2, …

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There’s something for everyone in Sleepy Hollow Country —farmers markets, live music, street fairs, historic homes, hiking trails, kayaking and boating on the Hudson River. Halloween season brings even more for the whole family—haunted hayrides, blazing pumpkins, costumed 10K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow .

COMMENTS

  1. Halloween in Sleepy Hollow Country

    October in Sleepy Hollow. Halloween in Sleepy Hollow has something for everyone: haunted hayrides, Gothic mansions, blazing pumpkins, farmers markets, live music, street fairs, our famous Halloween 10K run (costumes welcome!), Halloween parade, and of course, the Headless Horseman! Most October events sell out, especially weekend time slots.

  2. The Horsemen: Sleepy Hollow Haunted House

    VIP tickets available for this all-new Sleepy Hollow haunted house! Event takes place in the bathhouse at Kingsland Point Park, 299 Palmer Avenue, Sleepy Hollow, NY. In partnership with the Village of Sleepy Hollow. 2023 dates: October 6th — November 5th (Thursday - Sunday). Timed entry, hours of operation vary by date.

  3. Sleepy Hollow Halloween: Ghost tales, cemetery tours and more events

    Sleepy Hollow 'Run For Your Life' Halloween 10K, Oct. 29 Experience historic and scary sites along the scenic Hudson River course. A best costume prize will be given.

  4. The Best Things to Do in Sleepy Hollow for Halloween

    The Headless Horseman sculpture. The Headless Horseman sculpture is an iconic must-see site when visiting Sleepy Hollow! Located across the street from the Legend of Sleepy Hollow sculpture, in the Route 9 median between Old Dutch Church and Philipsburg Manor restoration, this spectacular 18-foot-tall rust-colored work of art was created by local artist Linda Perlmutter and depicts the famous ...

  5. VISIT SLEEPY HOLLOW, NY A Real Halloween Town Tour

    Shop Sleepy Hollow art prints here🎃 https://www.etsy.com/shop/TheWoodlandLibraryWelcome to Sleepy Hollow & Tarrytown New York where every day can be Hallowe...

  6. Sleepy Hollow, NY: Your Guide to Halloween Season

    Sleepy Hollow is a small village in the Hudson Valley area of New York State. It is so named because of the famous writer Washington Irving who lived in the area and wrote "The Legend of Sleepy Hollow.". It's important to note that Sleepy Hollow proper is actually quite small. The surrounding towns are only a few minutes away.

  7. Ultimate Guide to Halloween 2021 in Sleepy Hollow and the Rivertowns

    Travel back in time with the Tarrytown and Sleepy Hollow historical society on a 1.5- or 2-hour tour of the area. The Hudson Independent recommends Tour #1: "TarryHollow: Irving, the Old Dutch Church and the Colonial Experience" for Halloween fun, though there are three popular tours available.

  8. 7 Spooky Halloween Events In Sleepy Hollow, NY

    3. Cemetery Tours. Visiting Sleepy Hollow's 90-acre cemetery is a must for all who come to visit. Perfect for all history lovers, sculpture fanatics, and anyone who enjoys pretty scenery. You can't visit Sleepy Hollow during Halloween and not book a cemetery tour.

  9. Sleepy Hallow Tickets, 2024 Concert Tour Dates

    Sunday 07:00 PMSun 7:00 PM 6/2/24, 7:00 PM. Belmont Park - Long Island, NY UBS Arena HOT 97 Summer Jam. Find Tickets 6/2/24, 7:00 PM. EXCLUSIVE | Ticketmaster now offers hotel deals! Save up to 57% off your stay when you bundle your ticket with a hotel. Promoted.

  10. Home

    Sleepy Hollow, New York. Visit Sleepy Hollow's calendar of events is the most complete guide to planning your visit.. Our Halloween in Sleepy Hollow page is a quick guide to major events where you will find classics The Great Jack O'Lantern Blaze, the Haunted Hayride, Hulda's Night and the gravity-defying Legend Cirque joined by new entry Sleepy Hollow Haunted House!

  11. Halloween in Sleepy Hollow Country

    1 Hour tour exploring the South End of the cemetery. Route includes hills, stairs and unpaved roads. Saturdays & Sundays from 11am-12pm & 1-2pm through November 26th. In October this tour is offered everyday from 1-2pm. Sleepy Hollow Cemetery South Gate - 540 N. Broadway, Sleepy Hollow, NY 10591.

  12. Tours and Events

    Tours and events. Whether you are a history buff, love sculpture, interesting cemetery symbolism, or just want to enjoy the pretty scenery, a visit to historic Sleepy Hollow Cemetery's 90-acre grounds is a treat. Make the most of your time here by taking one of our guided tours to unlock some of the secrets behind the stones! Thank you so ...

  13. Sleepy Hollow Cemetery Guided Tours

    21 reviews and 50 photos of SLEEPY HOLLOW CEMETERY GUIDED TOURS "Great way to experience the Sleepy Hollow Cemetery especially during the Halloween season. This tour was organized well and having lighted lanterns to guide our path added to the spooky fun. Parking was on the cemetery property so don't get confused like we originally were and park at the Horseman's Hollow event which is a mile ...

  14. Spooktacular Sleepy Hollow at Halloween Weekend Getaway!

    Check Out Kykuit Rockefeller Estate. Address: 381 N Broadway, Sleepy Hollow (meeting location for tour) Located in the Pocantico Hills above Tarrytown and Sleepy Hollow with sweeping views of the Hudson River and Valley is one of the most prestigious and historic estates in Westchester County.

  15. The Legend of Sleepy Hollow at Washington Irving's Sunnyside

    Explore "The Legend of Sleepy Hollow". At this family-friendly happening, visitors can tour Washington Irving's house—decorated for the season—watch an original shadow puppet short film, and enjoy games on the lawn. A special exhibit highlights how the Legend has lived in the imagination of popular culture through the centuries since ...

  16. Moscow metro tour

    Moscow Metro. The Moscow Metro Tour is included in most guided tours' itineraries. Opened in 1935, under Stalin's regime, the metro was not only meant to solve transport problems, but also was hailed as "a people's palace". Every station you will see during your Moscow metro tour looks like a palace room. There are bright paintings ...

  17. Moscow Metro 2019

    Themed tours; Customized tours; St. Petersburg; SMS: +7 (906) 077-08-68 [email protected]. Moscow Metro 2019. Will it be easy to find my way in the Moscow Metro? It is a question many visitors ask themselves before hitting the streets of the Russian capital. As metro is the main means of transport in Moscow - fast, reliable and safe ...

  18. 628DirtRooster

    Welcome to the 628DirtRooster website where you can find video links to Randy McCaffrey's (AKA DirtRooster) YouTube videos, community support and other resources for the Hobby Beekeepers and the official 628DirtRooster online store where you can find 628DirtRooster hats and shirts, local Mississippi honey and whole lot more!

  19. Mimsa AlĂŒminyum

    Established in 1978, Mimsa Aluminium is one of the prominent companies in the industry with over 40 years of industrial experience and aluminum applications which are suitable for any project ranging from large-scaled commercial structures to small-scaled private residences. Company Profile ->.

  20. Events from May 25

    Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about Washington Irving, his impact on American Literature and the enduring appeal of "The Legend of Sleepy Hollow", which recently celebrated its Bicentennial. ... For the latest on Fall events, visit our guide to Halloween in Sleepy ...