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Mystery Day Trips with Guess Where Trips Ontario

Are you a big fan of day trips? There’s just something about hitting the open road and visiting a different place for a day.

Let me introduce you to Guess Where Trips!

A local Ontario company that is redefining road trips. They create exciting surprise itineraries that take you to new places you’ve never been before.

Just when you thought you knew every quaint little town or hiking trail or historical site Guess Where Trips comes along and takes you to some new hidden gems!

Let me share how it works, and my experience using Guess Where Trips, more than once!

Table of Contents

How does guess where trips work, 1. choose your day trip.

The first step from the Guess Where Trip website involves selecting a one-day road trip tailored to your unique interests and preferences. You can factor in essential elements like driving time from your starting location.

Whether you’re a history and culture enthusiast, a beach lover, a fan of charming towns , or an avid hiker, there’s a road trip experience waiting for you.

You have the option to filter your choices based on specific needs. Are you travelling with a wheelchair? Seeking vegan-friendly options? Exploring with your family or furry friend in tow ? No worries – Guess Where Trips has you covered.

Or, if you want to leave it up to them, take the road trip quiz to see what suggested trips are best for you.

Each mystery day trips Ontario package is designed with utmost care and attention to detail. The best part? You won’t know your exact destination until the day of your adventure. It’s a delightful twist that keeps the excitement alive.

These trips are concentrated in key regions of Ontario, spanning from the charm of southwestern Ontario (Windsor to London) to the vibrancy of central Ontario (Toronto) and the historical appeal of eastern Ontario (Ottawa) .

Guess Where Trips takes the burden off your shoulders in planning an exciting day trip. They meticulously research and plan each itinerary, ensuring that your day is filled with delightful surprises and memorable experiences.

For only C$65, you can embark on a one-day surprise road trip that’s bound to leave you with cherished memories.

To make things even more convenient, you have the option to get their PDF package for $39. However, for those seeking the full experience, receiving the package in the mail is a treat in itself. The packages are not only filled with valuable information but also arrive in charming packaging, adding a touch of anticipation and excitement to your journey.

Guess Where Trips Locations

Guess Where Trips are found in the following locations:

• Ontario trips include the Greater Toronto Area, London, Windsor and Ottawa
• Alberta trips include Calgary and Edmonton
• British Columbia trips include the Vancouver area
• Nova Scotia trips include the Halifax area
• And, in many Eastern states (FL, GA, NC, DMV, NY, NJ, PA, CT) of the USA

Best Selling Guess Where Trips Ontario

Here’s a small sample of their cute day trips that are near Toronto (In GTA, the London and Windsor area)

Local Markets and Picturesque Towns

Funky Florals & Fine Wines

Weird & Wonderful Things

The Small Town Charm Trail

Outdoor Adventures & Scenic Roads

Bridges to Beaches

Takes you to a historic village, a riverside trail and a gorge

Must love wine, food and flowers

A secluded waterfall and unusual attractions

Brings you to quaint small towns full of charm

Takes you to cool attractions, good food and scenic roads

Off the beaten path to sandy beaches and picturesque bridges

2. Get your Package

Now that you have chosen your trip all you have to do is wait for your surprise package to arrive in the mail (shipping is included). You do have the option for express shipping (an additional cost) or virtual delivery (it’s just not as fun). There’s no better feeling than opening the mailbox to find your package has arrived!

In your package you will receive 5 envelopes – a ‘Before You Go’ plus four secret itinerary stops. Only open the ‘Before You Go’ envelope, at least the night before. The guide shares everything you need to know while still keeping the details of your day a secret. What you’ll find out is…

• what time you should depart (strongly recommend you depart by the suggested time to be able to take advantage of the full itinerary)
• a glimpse into your four surprise stops each with driving time and recommended duration
• what to wear, pack and bring with you
• how long the round-trip will take (time/km)
• frequently asked questions specific to your day trip

3. Pack your Bags

Your bag is packed, and you’re ready to jump in the car and hit the open road, but before you do, open the ‘Your First Stop’ envelope. It holds all the information about your destination, plus interesting facts and history.

Each of the four secret stops will have recommended options for additional side trips or mini-stops, try and explore as many as you can. 

Add the first destination into your GPS, and don’t forget every road trip needs some good tunes. Guess Where Trips has even supplied you with a road trip playlist on Spotify. Ok, now you’re ready – let’s go!

Your Mystery Trips Ontario Adventure Awaits

Every curated surprise itinerary will bring you to four destination areas. Each of the four stops is packed with information, travel tips, and maybe even some exclusive Guess Where Trips coupon codes for some select local businesses.

There will also be recommended roadside attractions and mini-side trips between stops. Your day will be brimming with activities that suit a wide variety of interests.

Even though your day has been meticulously planned, there’s still a great feeling of it being carefree and spontaneous. It’s the element of surprise!

My Guess Where Trips Review

I had so much fun on this mystery road trip that I did a second one called Vistas, Falls & Caves .

Don’t believe me? Just take a look at these Guess Where Trips Ontario reviews , they are glowing!

My Surprise Day Trip

You won’t read about any Guess Where Trips spoilers here. As much as I am eager to share the details of my amazing day trip, I hate to ruin the surprise for you.

All I will say is that my surprise trip is called ‘Secrets in the South.’ It included a scenic drive in the country to do some hiking, stopping by a lovely village that I’ve long had on my list to visit, going to a town with some historical attractions, and of course so much more!  

A ‘Choose Your Own Adventure’ is included in all mystery trips Ontario surprise itineraries.

In ‘Secrets of the South’ there are options for hiking, visiting an instagrammable spot, and a delicious winery. I was giddy with excitement the entire day. It was a memorable day trip full of surprises!

Gift A Trip

According to Forbes, the secret to happiness is spending money on experiences rather than things. So surely gifting experiences is the next best thing you can do!

Guess Where Trips offers a ‘Gift-A-Trip’ gift certificate. Their gift card covers the cost of one of their one-day surprise curated surprise road trips.

Either select one or allow the recipient to choose their own. I promise you the memories attached to this day trip are something your gift recipient will not soon forget.  

As a Holidaymaker

Guess Where Trips far exceeded my expectations. Every little detail is carefully thought out and planned, right down to the cute packaging.

Let Guess Where Trips plan your next day trip.

Guess Where Trips is not only for locals looking to discover hidden gems in their backyard, but it’s for tourists too. What a great way to experience the local area you are visiting in Canada . It’s bound to be a highlight of your trip!

Creator, Founder of Dream Plan Experience

She specializes exclusively in European travel and crafting unforgettable day trips within her home province of Ontario, Canada.

She has been travelling to Europe for over 35 years and has lived abroad in Germany twice. Revisiting countries and exploring them extensively to create in depth travel itineraries, destination guides and helping travellers plan their trips to Europe through her customized services.

She also is a co-partner in a woman-led company that offers luxury retreats in Europe offering immersive cultural experiences.

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Take a surprise day trip in Ontario with Guess Where Trips

Your bag is packed, and you jump in the car, ready for a road trip. But your destination? Well, that’s a secret! With Guess Where Trips, you can take a surprise day trip in Ontario and discover new destinations you may not have known about before. Would you do it? Would you toss aside planning and let someone else guide you?

NOTE: Travel is not recommended at this time. These posts are here to serve as inspiration when we can explore again. Hey there – this post likely contains affiliate links, which means I earn a commission (at no extra cost to you) if you purchase from them. This helps me earn a few dollars to run this website.

A big shout out to Guess Where trips for providing a free trip in exchange for this post. As always, options are my own and I won’t recommend anything unless I truly love it.

What is Guess Where Trips?

How does it work, what you need to know about guess where trips, surprise day trip in ontario, why go on a surprise day trip in ontario, my surprise day trip in ontario, take a surprise day trip.

Let me tell you, that was hard for me. I’m a type-A planner. I have spreadsheets and maps that help decide where to go and what to see along the way. Setting out on a trip with no idea of where I was going and what I would see when I get there was nerve-wracking.

Guess Where Trips wants to take all the planning and booking away from you and give you a fun, planned and surprise trip! The Ontario company creates curated itineraries based on the type of adventure you want to have and allows you to discover new places you may have never seen before.

They currently offer itineraries for a surprise day trip in Ontario.

First, you select your trip style. Guess Where Trips has several itineraries for a surprise day trip in Ontario, from adventurous areas to pretty places.

After selecting your trip and entering your contact information, you’ll have to wait for the surprise package to arrive in the mail.

The package includes a “before you go” guide that will give you all the need to know details without actually spilling the beans on where you’re going. You’ll also get your stop envelopes, which hold all the secrets within.

On departure day, you’ll likely want to leave early. Most of the day trips are within a couple of hours drive, but depending on where you are in the province, it could be longer. And the trips are a full day of adventuring. Meaning, you’ll want to hit the road early and get to your first stop.

Before you head off, open your first envelope and find out about your first destination and places to see along the way. Pack your day bag with comfy shoes, road snacks, sunglasses, a camera and some road trip tunes and get going!

RELATED: 25 best scenic lookouts in Ontario you have to see for yourself

The cost of the surprise day trip in Ontario includes the planned itinerary but doesn’t include transportation, meals or entrance fees. There are several food stop recommendations, and I definitely recommend bringing some snacks for the drive.

You’re basically getting a fun, planned out itinerary with places you may not have head about before. For the cost, which is currently listed at $55 CAD, is totally worth it. I mean, I know how much goes into planning a road trip and having it all built for you, in a fun and exciting way, is worth every penny.

The price is not per person but per trip. So, if you want to bring a carload of people or head our on a solo trip, you’ll pay just one price for each trip you take. And it can be taken on any day (just double check on your “Before You Go” guide since some stops will be closed on some days of the week, or closed for the season), so if the day you plan to go is crappy weather, you can save it for a day with better weather.

If you’re terrible at secrets and can’t help but peek at where you’re going, there are maps available online using a unique code.

RELATED: 52 day trips from Toronto for every traveller

Guess Where Trips offers at least eight different itineraries for a surprise day trip in Ontario, and they seem to keep growing. If you want to find hidden gems or if you’re looking for “instagrammable” places, there’s a trip for you. If you’re looking for a fun outing with your friends or a more fun outing with your significant other, there’s a trip for you. If you’re looking to discover new-to-you towns or new-to-you food stops, there’s a trip for you. Or if you want a complete surprise, then there’s a trip for you too!

Guess Where Trips offers the following itineraries for a surprise day trip in Ontario:

• Outdoor Adventures and Scenic Roads: which offers hiking, countryside driving, and delicious food stops.
• Funky Florals and Instagrammable Boardwalks: which offers wine, boardwalks and lots of flowers
• Pretty Places and Country Favourites: which offers markets, lavender, beaches and more
• Local Markets and Picturesque Towns: which offers picturesque towns and riverside fun
• Wine Time and Hidden gems: which offers markets, restaurants and wine
• Beaches and Breweries: which offers beaches, brews, food and paddling adventures
• Taste of the Country: which offers a local farm experience, wine tasting, and picnics
• Surprise me: which is for the spontaneous and indecisive who want a complete surprise.

There are so many amazing places in Ontario that go overlooked by those who want to visit the most popular sites, like the Bruce Peninsula, Niagara Falls and cottage country. From roadside stops to hidden gems, these secret trips will bring you to new and exciting places, all while playing a little surprise game.

Guess Where Trips is the perfect way to explore Ontario with your friends or significant other safely. It can be made the perfect gift for friends and family, or you can even treat yourself to a trip.

It’s so easy. You choose what type of adventure you want and They. Do. All. The. Work. For. You. I can’t stress how amazing it is to have a thoroughly planned trip without lifting a finger. I spend hours (sometimes days) crafting my trips to make it successful and enjoyable, but it was nice not having to do that at all and just enjoy the day.

I admit it was hard not to peek at where I was going! I am a type-A planner after all, and I just wanted to know. It was exhilarating to rip open the next envelope to see where I was going next.

RELATED: 22 best scenic bridges in Ontario you have to visit

Without giving away too many details, I spent the day on the eastern side of Toronto, stopping at a lovely little town I had not heard of before. I enjoyed my time wandering the streets, drinking iced coffee from one of the recommended stops.

Next was a hike where I could frolic in the forest, which is my happy place, but in a completely new area that, again, I had not heard of.

The third stop was a winery with an incredible view of the surrounding Oak Ridges Moraine landscape. But what I loved most was their takeaway charcuterie board. It was the best charcuterie board I have ever had.

The last stop was another adorable small town I had actually been to before, so I dived into some of the surrounding recommended stops that are included in the itinerary and was pleasantly surprised with where I ended up.

Sorry (not sorry) the photos and descriptions are so vague, but if you want to see where these trips take you, you’ll just have to see it for yourself!

Olivia Rutt

Olivia Rutt is the travel writer and photographer behind My Wandering Voyage, a travel website helping working millennials find time to travel. She shares insight in trip planning, travel inspiration and photography tips. Olivia hails from southern Ontario, Canada where she works in the media industry between travels. Follow Olivia on Instagram where she shares her travel photos, or catch up with her on Facebook or Twitter.

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Desperate to travel anywhere? Mystery trips will make it happen

May 12, 2021 • 5 min read

Ready for a surprise? © Hello World/Getty Images

Mystery trips - where you pay an agency to organize your vacation and don’t find out the destination until the last minute - have been a niche section of the travel industry for a number of years. With travel gradually returning to some countries, they’re betting on people wanting to shake up their routine and embrace spontaneity after many months of staying at home.

Lonely Planet reader Markus Wittich from Germany is a very frequent traveler, racking up 18 trips in 2019 alone. After more than a year of staying at home, the idea of holiday where he doesn't know the destination is extra-appealing to him right now.

“That Groundhog Day feeling is real! We've been stuck at home for over a year and it feels like every day has been kind of the same. Since there haven't been many - or any - pleasant surprises throughout the pandemic, a surprise trip could be a fun idea to visit places that haven't been on your radar before.”

For river cruise company Uniworld, that bet is already paying off. A 10-day Mystery River Cruise in June quickly sold out and a September voyage is on the horizon. CEO Ellen Bettridge confirmed to Lonely Planet the original idea actually came from their customers.

“Our guests communicated that they’re willing to travel anywhere to get back out there and explore the world again as vaccines began rolling out and the light at the end of the tunnel finally neared. We created the Mystery Cruise with that sentiment in mind, to spoil our guests and provide them with a surprise trip of a lifetime with all details and decisions taken care of.”

But after so long being careful, are travelers ready to hand over the reins to someone else, especially when safety is still such a top priority? A quick poll of Lonely Planet readers revealed a mixed bag; 21% said they would be more likely to take a mystery trip now but 27% of people said they would be less likely, expressing concerns of safety or the possibility of being exposed to COVID variants despite being vaccinated. But others were tempted by the novelty. Rachel Van Raan-Welch, a reader from New York City is torn.

“I LOVE the idea of a mystery trip, and especially after being more or less on lockdown for the past year, I'm totally up for traveling anywhere right now. But that's in a hypothetical world in which COVID suddenly totally disappeared. In reality, it's hard to know when ‘after the pandemic’ may be. I wouldn't be comfortable taking a trip without knowing where I'm going or what I'm doing, and I think I'll probably feel that way for a long time.”

Safety and reassurance are priorities of any travel company right now and established surprise travel agencies have been quietly changing up their offerings. Netherlands-based Srprs.me expanded their themed vacation packages to include self-guided road trips in 2020. As travel slowly returns to Europe, spokesperson Anneke told Lonely Planet that road trips remain the top choice for their customers.

“We only send our travelers to safe destinations, so there's no need to stay updated on the travel advice to decide where to go; we do that for them. I think that people definitely still have an appetite for the mystery [and] spontaneous element, but under the current circumstances they prefer the more 'safer mysteries', such as our road trips closer to home.”

Of course, there’s another big reason why many seasoned travelers want to try out a mystery trip and it has nothing to do with the pandemic. “I sometimes plan out my trips too much by researching all the restaurants, museums and sights that I absolutely want to visit,” Markus says. “This can sometimes eliminate the opportunity to being spontaneous. Not knowing the destination before you arrive at the airport forces you to keep an open mind and to go with the flow.”

“Please sign me up!” he adds.

5 mystery trips you can book right now

Pack up + go.

A surprise travel agency specializing in domestic US vacation packages. After a personalized survey, they’ll send you to a mid-size US city with a list of curated recommendations. Since COVID, they also have a Staycation option to explore closer to home. 

Guess Where Trips

Embracing the hyper-local, this Canadian company specializes in creating itineraries around Ontario. They are all self-guided which means it’s a great budget option when you really want someone else to do all the planning for you. They are expanding their offerings to trips starting from Vancouver soon. 

Uniworld Mystery River Cruise

A 10-day river cruising experience, the first voyage in June this year has already sold out and a second date added in September due to popular demand. Everything is included in the price and you’ll be sent a detailed recommended packing list beforehand, One thing you’ll need for definite is your passport. 

With departure airports in Europe, this company specializes in city breaks and has a few different themes that you can choose from or you can specifically request them to send you somewhere new. Self-guided road trip itineraries are also available from the UK, Belgium, Denmark and the Netherlands. 

Departing from the UK, Spain, Germany and more, this is a straightforward surprise platform where they will set you up with a flight and a hotel. There is no option to customise with your interests though you can veto a few places during your booking process. 

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Top 13 Day Trips to Take from Ontario

Niagara falls , algonquin provincial park , prince edward county , sandbanks provincial park, muskoka lakes farm & winery .

• Canada's Wonderland 

Mount St. Louis Moonstone 

Blue mountain ski resort.

• Elora Gorge Conservation Area​

1000 Islands

Point pelee national park, long point provincial park, the village of st. jacobs.

Alright, who said you’ve got to part with your hard-earned cash for a fancy vacation on the other side of the world? Sometimes the best getaways are just a quick jaunt from home.

The beautiful province of Ontario is home to so many awesome destinations that you can explore in a day’s trip. It’s bursting at the seams with natural beauty, cultural diversity, and heaps of history.

So welcome to our list of day trip ideas in Ontario! Keep on reading, and let’s find your next one-day wonderland.

View this post on Instagram A post shared by Niagara Falls (@niagarafalls)

Website: https://niagarafalls.ca/  

When we’re talking about day trips from Ontario, there’s honestly no way we can’t mention Niagara Falls. Seriously, sights like this can make you feel all sorts of things.

Let me tell you about this little agency that’ll make your Niagara Falls day trip even more seamless: See Sight Tours . They have it all figured out; they’ll whisk you away from Ontario and take care of all the nitty-gritty (we’re talking transportation and tickets).

You can also hop on board a Hornblower Niagara Cruise and get right up close to the falls. Like, close enough to feel the spray on your face. It’s a real thrill, and you’re bound to end up with some damn impressive photos.

And when you’ve had your fill of water action, it’s time to explore the area. There’s a little old place called Clifton Hill that’s packed with all sorts of family-friendly shenanigans.

Local tip: For the best experience, try to visit on a weekday to avoid the weekend crowds.

View this post on Instagram A post shared by Algonquin Provincial Park (@algonquin_pp)

Website: http://www.ontarioparks.com/  

Address: Ontario 60, Ontario

Contact details: +1 705-633-5572

Operating hours:

• Open year-round

Algonquin Provincial Park is Ontario’s oldest and largest provincial park , spanning over a whopping 7,653 square kilometres. So, grab your hiking boots and your sense of adventure, ’cause there’s so much to do here.

There are over 15 marked trails of varying difficulty. The Lookout Trail is particularly epic, with a panorama that’ll have you reaching for your camera faster than you can say “Instagram-worthy”.

But hold on, it’s not just about burning off that morning’s bacon butty. Algonquin is famous for its wildlife too, so keep an eye out for the locals—moose, deer, and plenty of bird species call this place home.

Once you’re all tired out from exploring, drop by Algonquin Visitor Center. It’s a treasure trove of information on the park’s natural and cultural history.

Local tip: If you can, grab a map of Algonquin Provincial Park before your visit. It’ll help you plan your day better, and you won’t miss out on any highlights!

View this post on Instagram A post shared by Prince Edward County (@visitthecounty)

Website:   https://www.visitthecounty.com/  

Contact details: https://www.visitthecounty.com/contact-us  

Prince Edward County is a haven of all the things you’d like for a perfect getaway: wineries, food galore, and stunning landscapes. It has over 40 wineries to explore, each with their own unique vibe.

Most of them actually welcome daytrippers for wine tastings! Taste-test your way through the county and discover that perfect bottle—the one that’ll make all your friends jealous.

We can’t guarantee you won’t leave with a trunk full of new wine favourites, but hey, who could blame you? Anyway, you can also visit the lovely Bloomfield or hit Wellington for a fantastic meal.

But wait, there’s more! PEC also boasts some fabulous beaches that’ll have you questioning whether or not you accidentally slipped into paradise.

Local tip: Plan your winery visits ahead of time and leave room in your schedule to visit a lavender farm or a brewery—there’s tons to explore!

View this post on Instagram A post shared by Sandbanks Provincial Park (@sandbankspp)

Website: http://www.ontarioparks.com/park/sandbanks  

Address: 3004 County Rd 12, Picton, ON

Contact details: +1 613-393-3319

• Monday to Sunday – 8 AM to 10 PM

Nestled in—you guessed it—Prince Edward County, Sandbanks is famous for its ridiculously large sandy beaches and towering sand dunes. Honestly, with the waters and long stretches of sandy beaches, you will ask yourself if you’re still in Ontario.

It’s one of the largest freshwater baymouth sandbar systems in the world, which is a mouthful to say. But all you need to know is that it’s an ideal spot for beach lovers like you and me.

Beyond soaking up the sun, Sandbanks has some cool trails for those who like to wander. Check out the Woodlands Trail or the Cedar Sands Trail to stretch your legs and explore the dunes and diverse vegetation that call this place home.

Once you’ve had your fill of sun, sand, and scenery, why not fire up the BBQ? Sandbanks offers picnic areas and BBQ facilities, and there’s nothing quite like catching one of those fiery sunsets while enjoying a nice, relaxing meal.

Local tip: Sandbanks can get busy during summer weekends, so plan to arrive early in the day to secure a good parking spot.

View this post on Instagram A post shared by Muskoka Lakes Farm & Winery (@johnstons_cranberries)

Website:   http://www.cranberry.ca/  

Address: 1074 Cranberry Rd, Bala, ON  

Contact details: +1 705-762-3203

• Monday to Sunday – 10 AM to 5 PM

Muskoka Lakes Winery is tucked away in Bala, also known as the Cranberry Capital of Ontario. And yep, you guessed it, it’s all ’bout them cranberries!

No trip to Muskoka Lakes Winery would be complete without sampling their signature cranberry wines. Best part? You get to sip the good stuff while gazing out at the lush cranberry marsh. 

This place offers tours that get you right into the action. Talk about hands-on experience! Harvest season (from late September to October) even allows you to get your feet wet in a cranberry plunge. 

Oh, and did I mention that this place isn’t just a winery, it’s a farm? A farm that offers beautiful trails for hiking, giving you a chance to burn off that wine-induced euphoria, and enjoy the diverse flora and fauna. 

Local tip: Muskoka Lakes Winery is a seasonal business, so do check their opening dates and times before planning your trip.

Canada’s Wonderland 

View this post on Instagram A post shared by Canada's Wonderland (@canadaswonderland)

Website:   https://www.canadaswonderland.com/  

Address: 1 Canada’s Wonderland Drive, Vaughan, ON

Contact details: +1 905-832-8131

• Sunday to Thursday – 10 AM to 8 PM
• Friday and Saturday – 10 AM to 10 PM

Canada’s Wonderland is an epic theme park located in Vaughan, Ontario—just a hop, skip, and a jump from Toronto. This place has more roller coasters, games, and excitement than you can shake a stick at.

We’re talking over 200 attractions—17 roller coasters alone! Whether you’re into crazy plunges that hurtle you in a free fall, or you’ve got a thing for twists, turns, and loops, Canada’s Wonderland ain’t playin’. 

Don’t forget about Behemoth and Leviathan, two of the tallest and fastest coasters in North America. You’ll be screaming your heart out before you know it!

Wonderland’s got you covered with a water park too: Splash Works (opens typically from June to September). And when it comes to food, well, Wonderland’s got more options than you can chew (pun intended). 

Local tip: Go on a weekday if you can, especially early in the season or after the school rush. The lines will be shorter, giving you more time to experience everything this amazing park has to offer.

View this post on Instagram A post shared by Mount St. Louis Moonstone (@mtstlouismoonstone)

Website: https://www.mountstlouis.com/  

Address: 24 Mt St Louis Rd W, Coldwater, ON

Contact details: +1 705-835-2112

• Monday to Friday – 9 AM to 4 PM

Love it or hate it, there’s one thing winter is good for: strapping on your skis or snowboard and hitting the slopes. Especially at Mount St. Louis Moonstone, the “I can’t believe it’s not in the Alps” ski resort in Ontario.

This resort has runs for all skill levels, from bunny hills for beginners to challenging black diamonds for the hardcore. They’ve even got one of the largest terrain parks in Ontario for all those freestyle junkies itching to practise their tricks or flips.

And, with 36 slopes, traffic jams are a thing of the past—unless you count running into a rogue snowman. This place is more than just a great run, though.

It’s got rentals if you’re not keen to lug your gear around and instructors if you want to level up your ski or board game. And when you’re ready to thaw out for a bit, cosy up by the fireplace in the chalet with a cup of hot cocoa.

Local tip: And, parents, if you’re worried about keeping the little ones entertained while you carve up the snow, don’t fret. Mount St. Louis Moonstone offers ski lessons for kids and various events organised throughout the winter season.

View this post on Instagram A post shared by Blue Mountain Resort (@bluemtnresort)

Website: https://www.bluemountain.ca/  

Address: The Blue Mountains, ON

Contact details: +1 833-583-2583

• Monday to Sunday – 9 AM to 10 PM

Nestled along the shores of Georgian Bay and just a two-hour drive from Toronto, Blue Mountain Ski Resort has it all. It has 42 ski and snowboard trails, and they even offer night skiing.

This resort has got your back, no matter the season. I’m talkin’ golf, hiking, zip-lining, scenic gondola rides, and even a mountain coaster they call the Ridge Runner.

If a slower pace is more your cup of tea, the Village at Blue Mountain has heaps of stuff to do too! You can meander through the quaint streets, indulge in some retail therapy, and dip into the tasty food scene.

You can even check out the on-site spa or relax at the resort beach. Who says you can’t have the best of both worlds—action-packed fun and some well-earned downtime?

Local tip: Everybody loves a good deal, so keep your eyes peeled for their various packages throughout the year. You might just score the perfect day trip at a sweet price!

Elora Gorge Conservation Area ​

View this post on Instagram A post shared by Parth Vira (@random.parth)

Website:   https://www.grandriver.ca/en/outdoor-recreation/Elora-Gorge.aspx  

Address: 7400 Wellington County Rd 21, Elora, ON

Contact details: +1 519-846-9742

• Monday to Sunday – 8 AM to 9 PM

Perfect for a day trip, Elora Gorge Conservation Area is where Mother Nature struts her stuff big time. Just under two hours from Toronto and you’re greeted with an epic, 22-metre-high gorge carpeted by forests and by the meandering Grand River.

This place is famous for tubing and kayaking, where you get to surf the river down the stunning gorge itself. No joke, these are rapid-filled rides that’ll tickle your wild side and give you a legit splash-tastic time.

Feeling more “earthbound” for the day? Don your walking shoes ’cause the Elora Gorge Trail is not to be missed. 

It’s a killer 5km walk with killer views of the limestone cliffs and cascading waterfalls. Pack a picnic, find a cliff-top spot, and chow down with a view. 

Local tip: Early birds catch the worm (or rather, the calm waters and quiet trails), so try to arrive in the morning to avoid the crowds.

View this post on Instagram A post shared by Town of Gananoque (@travel1000islands)

Website: https://visit1000islands.com/  

Address: Leeds and Grenville United Counties, ON

Contact details: +1 315-482-2520

• Winter Season (October 10th – December 31st) and (January 1st – May 16th):

Tuesday to Saturday – 10 AM to 12 PM, 1 PM to 4 PM

• Spring Season (May 17th – June 24th):

Monday to Sunday – 9 AM to 12 PM, 1 PM to 5 PM 

• Summer Season (June 28th – September 3rd):

Monday to Sunday – 8 AM to 7 PM

• Fall Season (September 7th – October 9th):

Monday to Sunday – 9 AM to 12:30 PM, 1 PM to 5 PM

Now, one of the best things to do here in 1000 islands (besides gawking at the gorgeous scenery, of course) is to hop on a boat tour. It’s kinda a must-do, y’know? 

There are loads of different tours to choose from too. You could go on an international tour and check out both the Canadian and the US sides, which is super cool. 

And let me tell you, these islands have plenty of history and culture to dig into as well. For instance, the Boldt Castle on Heart Island is straight out of a fancy romance novel, with its tragic love story and all. 

And then there’s Singer Castle on Dark Island, which boasts great architecture and an even greater past. Of course, no trip to the 1000 islands would be complete without trying some locally made food—so make sure to bring your appetite along! 

Local tip: Don’t miss out on the loaded fries at the local chip trucks scattered nearby, trust me, they are a delight!

View this post on Instagram A post shared by Point Pelee National Park (@pointpeleenationalparkcanada)

Website: https://parks.canada.ca/pelee  

Address: 1118 Point Pelee Dr, Leamington, ON

Contact details: +1 519-322-2365

• Monday to Friday – 6 AM to 10 PM

Point Pelee National Park is the southernmost tip of mainland Canada, which is pretty neat if you ask me. You should definitely hit up the famous Tip, a land spit that reaches right into Lake Erie. 

You’ll feel like you’re standing on the edge of the world, fo’ real! And let’s talk about activities, ’cause there are plenty! 

For all the birdwatching lovers out there, Point Pelee is the place to be, especially during spring and fall migrations. In fact, it’s a hotspot for all sorts of critters—butterflies, frogs, and so much more!

But hey, even if you’re not a wildlife enthusiast, the park’s got your back with its lush forests, sandy beaches, and of course, amazing hiking and canoeing opportunities. 

Oh, and make sure to swing by the park’s Visitor Centre, where you can get your hands on all sorts of info about the park, its history, and the really cool stuff it has. 

Local tip: If you’re visiting the park between May and September, don’t miss the Freighter Canoe Rides – it’s a unique and engaging way to explore the marsh with local guides!

View this post on Instagram A post shared by blogTO (@blogto)

Website: https://www.ontarioparks.com/park/longpoint  

Address: 350 Erie Blvd, Port Rowan, ON

Contact details: +1 519-586-2133

• Monday to Sunday – Open 24 hours

Long Point Provincial Park is not your typical run-of-the-mill park; it’s a huge sand spit on Lake Erie, and guess what? It’s also a UNESCO World Biosphere Reserve.

Literally thousands of bird species pass through here, making it a paradise for birdwatchers. Now, putting birds aside, let’s talk about beaches.

The park boasts some seriously stunning beachfront. We’re talking about sandy beaches that stretch on for miles and miles, perfect for a day of lounging, swimming, or some quality sandcastle building!

And hey, if you’re feeling adventurous, you can also rent a canoe or kayak and explore the nearby wetlands—pretty cool, eh? And before your day at Long Point comes to an end, make sure to soak in those epic sunsets—they’re really something special!

Local tip: Make sure to explore the Long Point Lighthouse for a sweet photo-op and a little taste of nautical history.

View this post on Instagram A post shared by Stroll Walking Tours | Waterloo Region (@strollwalkingtours)

Website: http://www.stjacobsvillage.com/  

St. Jacobs is this delightful little spot, often overlooked, but believe me, it’s a hidden gem. The main street of the village is brimming with glorious, unique shops .

And talk about variety; they’ve got quaint restaurants, bakeries, and delightful treats to indulge in. Let’s not forget the Farmer’s Market with abundant local produce; it’s a wholesome experience.

And then there’s the history and culture side of things. The entire village is an embodiment of the simplicity and tradition of the Mennonite community.

You’ll find the St. Jacobs Mennonite story an intriguing tale told in their very own interpretive centre. A horse-drawn trolley tour? Heck yeah, they have that too, to give you a taste of good ol’ farming life.

Local tip: Try their famous apple fritters at the Farmer’s market; they are out of this world good!

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One of the Best Day Trips from Toronto: Can you Guess Where?

by janecanapini | Nov 21, 2021 | Canada , Ontario , Trip Planning

The package arrived in the mail looking like a communiqué from a spy agency: an outer envelope with only my name and address and the cryptic “Guess Where Trips’ logo in the corner. Inside, a dossier containing 5 sealed envelopes, and a printed ‘Hey Travellers!’ introductory note, telling me that I must open the envelopes in the order specified, starting with the one titled Before You Go. I was hooked! In my hands I held everything that Henk and I needed to set out on a surprise day trip from Toronto that promised to deliver ‘”outdoor adventures and scenic roads”, and all we needed to do was start by opening the first envelope. Curious, impatient and eager to know what was in store for our day, I ripped into the first envelope and our adventure began!

Guess Where Trips: Sponteneity Wrapped Up in Detailed Planning

The concept behind Guess Where Trips is fun and simple: instead of you doing all the planning for your road trip, researching where to go and what to do when you get there, someone else does the work for you, curating interesting experiences and stops along the way. The company offers all kinds of surprise day trips from Toronto, as well as from other major cities in Ontario and Canada. All you have to do is pick the theme for your trip based on a few parameters (your origin city, how far you want to drive), and a few preferences (family-friendly, food-centric, outdoorsy, etc) and then you are served up a themed package with all the details you’ll need for a ready-made day trip.

As a super-planner when it comes to all of our own day trips from Toronto and elsewhere, I have to admit it was very liberating to give up control and leave behind all the legwork – and guesswork. And since a surprise road trip sounded like just the sort of adventure our Covid-weary routine needed, Henk and I excitedly piled into the car and set off.

Our Day Trip from Toronto: SPOILER ALERT!

If you don’t want to know where our Guess Where Trips package took us and what Henk and I saw and did, stop reading now! But if you would like to see where our road trip adventure led, read on – because this turned out to be one of the best day trips from Toronto that we’ve taken!

Envelope 1: “Before You Go”

Our first envelope was a practical one, offering up tips for what we should wear, how long we could expect to be on the road, distance between stops, how much time to allot at each stop, etc. It was actually recommended that we open this envelope in advance of our actual trip, so we would have some information to help us choose our departure day, while still keeping the destination a mystery.

Our next Envelope: Our First Stop

It was a particularly beautiful Sunday morning in September when Henk and I decided to pull the trigger on our Toronto day trip. Like two kids excited to open a present, we unsealed the first envelope, where we learned that we would be going east from Toronto, en route to Port Hope, “a cute town with a few surprises'” about 2 hours away. So we donned our sunglasses, piled into the car and hit the road!

TIP: The Guess Where Trips envelope even included a QR code that brought up our destination on our cell phone to help with directions.

One of the surprises mentioned in our itinerary turned out to be a “ghost town” along the way called Wesleyville that was listed as an optional pit stop. Always game to see a ghost town, (provided there are no actual ghosts), Henk and I took this short detour to explore what was left of this 19th-century hamlet. All that remains today of this former town is a schoolhouse built in 1860, and a church dating from 1899, both of which are being restored by the local community. But what was more interesting to Henk and I was the church graveyard, as it holds families that date back generations.

Walking around this cemetery we did find a few particularly photogenic gravestones – some cryptic (pardon the pun!), some succinct, and some with a sense of humour.

TIP: Even though visitors are welcome, always try to be respectful when visiting any type of cemetery, whether it is a rural one in wine country tied to a bit of local lore , or a famous one in Argentina with infamous names on the tombs.

“A Town with a Story”: One of Ontario’s Best Preserved Main Streets

Next up on our road trip was Port Hope , a charming town of about 16,000 people that neither Henk nor I had ever visited. The town definitely lived up to its reputation as ‘cute’, but not just because of its large number of heritage buildings in the historic downtown (which makes this particular downtown one of the largest and best preserved in Ontario).

Port Hope also has cute boutiques on Walton, it’s main street, featuring local designer clothing (check out Poho Boho ), funky and on-trend home decor stores, and of course several nice cafes and restaurants. Plus there were beautiful walking paths along both sides of the Ganaraska River that flows through the downtown.

But the surprise even the Guess Where Trips organizers couldn’t have planned waited for us in the actual Ganaraska River itself: dozens of people standing shin-deep in the water along the edges of the river, fishing rods and nets in hand.

It turns out that by pure coincidence, Henk and I had timed our visit at the end of the Ganaraska River salmon run!

A Serendipitous Salmon Run

The first time Henk and I had seen a salmon fun was on Manitoulin Island at Bridal Veil Falls , so once we realized what was happening, we parked ourselves on the pedestrian bridge that spans the river for a bird’s eye view of the action.

Dozens of enormous salmon were swimming upstream below us, the occasional one taking the bait of a lucky fisherman who then had to negotiate the current, avoid getting tangled in other fishing lines, and try to land the struggling fish.

Kudos to the successful fishermen and fisherwomen who managed to reel in one of these 20-plus-pounders, and what a treat to be able to watch it all go down from our sunny perch.

Our surprise salmon run kept us in Port Hope longer than expected, but that is the beauty of a mystery road trip: you never know what you’ll find. All the same, I was keen to head to another place featured on our itinerary that I had actually discovered myself months ago when I was researching day trips in Ontario , but never had a chance to visit: a larger-than-life store-cum-attraction called Primitive Designs .

Primitive Designs Appeals to the Kid in Everyone

When I first found Primitive Designs online, I couldn’t wait to take a trip out to see this place for myself. So I was thrilled when I saw that our Guess Where Trips itinerary included this stop just outside of Port Hope. What I wasn’t prepared for was the popularity of this place, probably more so on the day we arrived because it happened to be a gorgeous sunny Sunday.

One look at the 26-foot tall Transformer welcoming visitors at the entrance and it was easy to see why this place attracts all kinds of people, from families with kids, to gamers, to shoppers who love the exotic, to forever-young grownups like Henk and I. After all, who wouldn’t want to see Optimus Prime ‘in the flesh’, or life-sized dinosaurs and velociraptors made out of recycled metal salvage, not to mention mythical creatures, and oh, yes, an Iron Throne! But just exactly what was this place and what was the story behind it?

So Much More Than a Retail Store

Despite appearances to the contrary, Primitive Designs is not some kind of amusement park; the barn-sized central building is actually a massive retail shop that houses all kinds of exotic imported goods and artesanal products from around the world. There are colourful chimineas, beautiful wood carvings, mosaic bowls, textiles and masks.

But without a doubt it is the larger-than-life sculptures and art pieces around the property that have put Primitive Designs on the map.

I was curious to know how all this had come about, so when I spotted someone who looked like he was in charge, I went up to him and introduced myself. My instincts were correct, as the man in charge was Ron Dacey, who is not just the owner of Primitive Designs along with his wife Rhonda and son Maximus, but the creative mind behind the giant installations here.

A self-proclaimed hippy who lived the couch-surfing, back-packing life of a free spirit in his youth, Ron is a born entrepreneur. Even while travelling the world on a shoestring, he saw opportunity in every craft market he visited, buying the unique products he found and selling them to Europeans to help fund his travels.

Ron’s humble start selling products from the back of his Volkswagen evolved into a successful business as an importer in Toronto. He translated his passion for travel and his eye for exotica into a 17-year business as a vendor at Toronto’s Harbourfront Antique Market. It was in Toronto where Ron met Rhonda Cook, a businesswoman herself who had worked in the eclectic Queen Street West neighbourhood for years. But it was when the two of them decided to move to Port Hope and establish Primitive Designs twenty years ago or so, that Ron got to really indulge his creative side – in a big way.

A Global Enterprise

Working with overseas artisans he has met during his global travels and buying trips, Ron translates his own creative sketches and designs into giant handcrafted art pieces. Built in southeast Asia using upcycled metal salvage, these giant sculptures are shipped to the Port Hope property where they are assembled and installed by Ron and his team.

In pre-Covid years, Ron would typically swing by these overseas workshops during his travels to check on the progress of said sculptures, but for the past two years because of Covid, he’s been relying on long-distance communication only. But that has also given him time to get more hands-on with some of the builds, like the Kraken attacking a sailing ship, where Ron did much of the re-design and construction of the ship himself.

A Family Affair

Primitive Designs is definitely a passion project for the whole family: Rhonda manages much of the retail business, and it was their son Max who did all the research on the dinosaurs to ensure that the metal versions you see on the property are actually built to scale, with details based on actual dinosaur specimens that have been discovered and documented.

And when they aren’t working their Primitive Design business, you’ll find Ron and Rhonda down in Belize where they have a few other projects on the go. (And yes, I’m a little jealous of their lifestyle, I gotta say!)

TIP: It’s free to visit Primitive Designs and photograph any of their art pieces, but there are ‘donation buckets’ beside them if you’d like to contribute to help support Ron and Rhonda’s charity work in Belize .

Our Second Stop… “An Easy Adventure”, but first…Goats!

The beautiful thing about surprise adventures is you never know who you will meet or where you might end up, which in our case turned out to include a short detour from our planned itinerary to check out a business that Rhonda had recommended…the Haute Goat farm a short drive from Primitive Designs.

Haute Goat Farm

Like the name suggests, Haute Goat Farm is very goat-centric, from goat yoga classes that are offered al fresco in the warmer months, to the Screaming Goat cafe on-site that serves locally-sourced goat milk products like ice cream and a particularly delicious mac ‘n’ goat cheese. But the farm is also a great destination for a rural outing with lots of trails available on the farm and the opportunity to interact with other animals, including Alpacas.

Kids would love this farm experience, but there are also activities that cater more to grownups, including an overnight B&B package called the Alpaca Sleepover where you can stay in a comfy cabin inside the Alpaca enclosure, and wake up to the sound of roosters.

Our impromptu visit meant that Henk and I only had time for a short visit, but the unexpected detour made for a nice stop for lunch and was worth checking out since we were literally in the neighbourhood.

TIP: If you don’t want to sleep overnight next to the Alpacas, visitors can book an ‘Alpaca Knuffle Shuffle” where you can get to engage with Alpacas and walk them along some of the trails.

Speaking of farms and trails….

After briefly saying hello and goodbye to the goats and alpacas, Henk and I got back onto our Guess Where Trips itinerary, and headed out for a hike in the Carstairs Tract, the ‘easy adventure’ promised in our Second Stop.

Seventy-five years ago Carstairs Tract was cleared for farming, but the property has since been replanted first as an educational arboretum, and later with more local tree species. Today this accessible forest offers pretty shaded trails where visitors can learn how to identify local trees, or just enjoy an easy shaded walk . (which in our case involved photographing some interesting mushrooms, too.)

Our Third Stop: “An Italian Countryside”

Wait, what? There’s an Italian vineyard in Northumberland County?

Welcome to Villa Conti , 100 acres of rolling hills owned by Italian chef Tommaso Conti, who had his eye on this rural property for several years before purchasing it and moving here in 2015. An experienced restauranteur and caterer who owned a restaurant in Toronto for many years, Conti’s dream for the Villa was to open a restaurant offering authentic rustic Italian dishes, restore the neglected vineyards in order to produce his own wine, and recreate a bit of his own rural Italian upbringing.

Again, as luck would have it, our timing was perfect for our visit: Henk and I happened to arrive on the same day that Tommaso was hosting a thank-you lunch for friends and family who has just helped bring in the grape harvest. Lunch was over but it looked like the celebration was just starting, because before we knew it, kids and adults alike were crushing grapes alla ‘Lucille Ball’, up to their knees in purple grape juice and stomping their bare feet to the tune of La Tarantella .

Tommaso invited Henk and I to join in, but even though we didn’t stomp the grapes ourselves, we definitely felt like we were part of the festivities. With the late afternoon sun turning the vineyards golden, a plate of charcuterie to share and a glass of ‘Villa Conti Red’ in hand, we could just as easily have been somewhere in the Abruzzese countryside! Salute!

Our Fourth Stop. “Choose Your Own Adventure”…or Save it ’til Later…?

The best thing about a Guess Where Trip is that you open each envelope one at a time, keeping the mystery alive until the next destination and its attractions are revealed. However, when you are like Henk and I, and take the time to ‘do it all’ at each stop, it’s easy to run out of time in your day before completing all 4 stops. Which is exactly what happened. Before we could begin to do justice to the places listed in our fourth envelope, the sun had dipped pretty low on the horizon, and we knew we wouldn’t have time to take advantage of all the things still left to see and do on this particular day trip from Toronto.

Which means only one thing: there’s another road trip in our future!!!!

That’s the great thing about one of these road trips….we can choose to ‘complete’ it whenever we want to, and having peeked at the suggestions in that last envelope, there’s easily enough for a full day’s worth of hiking, photography, dining and even beer! Plus there are other food stops en route to sample buttertarts and other goodies that we didn’t have time for on this trip.

Removing the Guesswork with Guess Where Trips

If you are even half as curious as Henk and I, love a little mystery, and like to take advantage of the serendipitous surprises that might appear along the way, a Guess Where Trip could be just your thing. Our Sunday drive turned out to be one of our best day trips from Toronto ever, and thanks to someone else doing all the planning, the guesswork was taken out of the whole process for us.

One thing still remains a mystery, though, and that is: what unexpected and interesting things are left to discover in that fourth envelope? Are you as curious as Henk and I to see what awaits…?

I guess you’ll just have to wait to find out, too!

TIP: Guess Where Trips packages cost $55 before tax and shipping. As a nice bonus, the organizers have negotiated special offers and discounts at many of the businesses they list, so look for these discounts in your itinerary and mention them if you do visit those places. And if you want to make your day trip into an overnight trip, just contact the Guess Where Trips folks who will be happy to make some suggestions for where to stay. How easy is that?

Jane Canapini is a member of the Travel Media Association of Canada and the North American Travel Journalists Association. She established GrownupTravels.com in 2014 to share information and tips based on personal experience so her readers could get the most out of their travels.

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Fun time had by all! Even me!

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How it Works

Magical Mystery Tours specializes in customized mystery trips. Travelers set the parameters, we put together a trip based on those specifications, and then travelers discover their destination upon arriving at the airport!

First, you complete our mystery travel survey and provide your trip specifications. Then we get to work putting together a getaway that’s individually designed and customized for you. A week before your trip, we email you a weather forecast, packing list, and flight departure time.

Shortly afterward, we mail your reveal packet containing a destination overview, why we chose it for you, all your trip booking information, and guidance on dining and activity options. You’ll take this sealed red envelope to the airport to open and discover where you’re headed!

Resist the temptation to rip it open early…this is all part of the mystery trip experience!

This vacation style means you don’t have to—can’t, even—spend hours poring over destination options, flight schedules, hotel reviews, lists of things to do, restaurant reviews, and so on. We handle all of the details, drawing upon our considerable travel knowledge and experience.

You simply get to revel in the anticipation and excitement and then show up and enjoy this unique travel experience, with the peace of mind that we have planned your trip just for you, based on the parameters you’ve provided. It’s stress-free and fun!

Are you intrigued? Let’s get started…

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From Oprah Winfrey and The New York Times to Vogue magazine and hundreds of satisfied clients, folks are raving about Magical Mystery Tours!

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Ever wondered if mystery travel is for you? Read these client testimonials in our Mystery Traveler Q&A series.

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Home » North America » Canada » 15 AMAZING Day Trips to Take from Ontario | 2024 Guide

15 AMAZING Day Trips to Take from Ontario | 2024 Guide

Ontario is the most populous province in Canada, home to both the country’s capital city of Ottawa and the dynamic city of Toronto. There is so much to do in this beautiful province, that you could easily spend months exploring the area.

It’s also conveniently situated on the Northern border of the USA, bordering a bunch of the Great Lakes and America’s Minnesota, Michigan, and the New York States. Depending on where you’re based, you might just be able to take a day trip across the border too!

Day trips are a great option for all types of travelers because they can give one a broader feel of the place you’re visiting. Not only will guided tours be super educational, but they’re also a great opportunity to reconnect with your family on a fun adventure. If you live in the area, full or half-day trips in Ontario are a cheaper alternative to a full-blown vacation.

We’re going to take a look at some of the local trips you can take in Ontario!

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Getting Around Ontario, and Beyond

Half-day trips in ontario, full-day trips in ontario, final thoughts on day trips from ontario.

No visit to Canada is complete without exploring Ontario and all it has to offer. Before we dive into some of the best Ontario day trips, let’s take a closer look at how to get around the area.

Like any large province or state, the biggest cities in Ontario (Toronto and Ottawa) have reliable, affordable, and safe public transportation. A lot of the inner cities also have buses, subways, streetcars, and ferries. 

In Toronto and Ottawa, these modes of transport connect metropolitan and suburban districts with extensive routes. A one-way ticket can cost around CAD$3.25, while a day pass will set you back CAD$13.50.

If you’re looking to move between cities, or explore Ontario’s roads-less-taken, you’ll have to consider other options. When you’re familiar with the area and venturing out on day trips without a tour guide, renting a car is the most convenient option. As with all car rentals, make sure you get insurance before you leave the lot!

The big Ontario cities are also all connected by railway, which is a great way to get from A to B when traveling across the province. VIA Rail Canada services the whole of Ontario, Ontario Northland services the north of the province, and GO Train connects Hamilton to Oshawa.

Not everyone has the time to explore far afield, sometimes a half day trip is all you can fit in. These half-day trips in Ontario will get you out of the city and seeing some of the best bits of the province.

For example, there’s plenty of things to do in Hamilton and it’s super close to visit!

Cobourg Beach 

Cobourg is a quaint lakeside town just west of Victoria Park on Lake Ontario, only an hour outside the city of Toronto by rail. Cherished by locals as a weekend haven, Cobourg Beach offers a blend of sand, grassland, and a picturesque boardwalk. 

Cobourg Beach is in fact two beaches. Most tours will take you straight to the main beach, also known as Victoria Park Beach, but there is so much more to explore along these sandy shores. 

The beach is designed for family fun, offering lots of amenities including bathrooms, restaurants, and splash pads for all types of visitors. They even host volleyball and sandcastle-building events throughout the year!

If you’re after a more secluded beach experience, the lesser-known West Beach is a local favorite. This beach has a more natural appeal and is less busy. An afternoon here can include relaxing on the beach, reading a good book, and swimming in the clean lake water. Bring along a picnic, because, unlike the main beach, West Beach has no food or beverage amenities.

When a single day trip in Ontario’s lake district isn’t enough, why not extend your visit and spend a few nights in this tiny house on the beach in Brighton near Cobourg Beach? It’s only a short drive from the lakeside town and has exquisite lake views.

Rattlesnake Point 

Located just an hour’s drive out of Toronto, Rattlesnake Point is a beautiful location for outdoor enthusiasts looking for a respite from the city. The mountainous woodlands are a top location for rock climbing, hiking, and trail running. 

Conveniently, there are no rattlesnakes in the area – yes, we were surprised by this too. In fact, the park gets its name from the snake-like path that cuts through the Niagara Escarpment.

Take note that reservations are required before you visit, so be sure to reserve your visit with Conservation Halton Parks.

Whether you go to the top of the Buffalo Crag lookout point or watch the eagles soaring overhead from beneath the thousand-year-old cedar trees, the landscape here is nothing short of extraordinary.

For something different, and if you have some extra time on your way back home, try out an oil painting class in nearby Erin Mills.

Packing in a day trip from Ontario is a lot more rewarding than taking half-day trips. By heading out before the sun rises, and leaving at the end of the day, you can easily pack in a full day of adventure and fun with your loved ones. These aren’t narrowed down for tourists alone, Ontario locals also love to explore their home!

Niagara-on-the-Lake

If you’re a first-time visitor to Ontario, Niagara falls will be at the top of your day trip list but there’s more to see in this lush region than just the waterfall. Only a two-hour drive from Toronto, Niagara-on-the-Lake is a small town near Niagara Falls which is packed with historic sites, galleries, parks, and restaurants.

The town has a heritage square which is well worth a visit, but it’s the surrounding Winelands that we are most excited about. Niagara Wine County is a quick 20-minute drive from the waterfall.

It’s the Napa Valley of Canada, and for good reason. The area is as lush and beautiful, and is home to over 20 top wineries that follow tons of different wine-making techniques. Some of our favorite wineries for a day trip in Ontario include the Jackson Triggs Winery, Pillitteri Estate, Stratus Wineries, and the Peller Estates Winery.

Niagara Wine County offers year-round wine tasting activities, but the most beautiful time to visit is definitely during summer and fall. Can you think of anything better than some bucket-list sightseeing combined with a wine tasting? 

Suggested trips: Winery Tour with Tastings & Lunch

Niagara Falls 

I have no doubt you’ve already planned your trip to Niagara Falls. Hell, I wouldn’t even be surprised if your entire Ontario trip is based around this visit. It’s one of the top places to visit in Toronto .

Over eight million visitors visit Niagara Falls State Park each year. While it’s not the biggest waterfall in the world, it certainly is one of the most impressive, with the world’s highest flow rate of about 700,000 gallons of water moving every second.

The waterfall lies on the border between Canada and the USA, and offers awe-inspiring scenery in every direction. If it’s the waterfall you’re most interested in (naturally), we recommend taking a boat cruise or a scenic helicopter ride over the waterfall (if you have the budget for it). 

If you’re feeling very adventurous, why not zipline to the falls ? Alternatively, a visit to the Skylon Tower observation deck offers equally breathtaking views, without having to get soaking wet.

However, there is so much more to see than first meets the eye. The adventure-packed area is a top location for hiking and also offers a bunch of family-friendly activities, entertainment, and dining. 

Suggested trips: Niagara Falls Day Trip and Day and Night Tour

Canada’s Wonderland Amusement Park

Visiting Ontario with young children? Perfect for family day trips from Ontario, Wonderland Amusement Park has been making visitors smile since 1981. The park features more than 200 attractions, including 17 roller coasters, two children’s areas, and a 20-acre water park.

It’s open year-round through all four seasons, and hosts daily live shows and special events throughout the year. When you visit around Christmas or Halloween, you’ll be treated to themed adventures.

That being said, Canada’s Wonderland isn’t just for youngsters, and the park is a top location for corporate adventures, vacations with friends, or a romantic trip. Like any world-class amusement park, it is home to fantastic dining and shopping arcades, which will be sure to keep you busy between rides.

Feel like turning this into an overnight stay? This comfortable townhouse is an ideal home overlooking the amusement park.

Blue Mountain and Collingwood

There’s nothing better than a good old trip into the mountains. The Blue Mountains are a two-hour drive from Toronto and offer adventures from summer through to winter. 

As a snowboarder myself, I’d highly recommend checking this mountain out if you’re visiting during the colder months. You’ll find a charming base village that leads up to over 15 ski lifts and an abundance of easy to expert terrain.

If skiing, snowboarding, and tubing aren’t for you, there is lots to keep you busy in the village, which is packed with cozy eateries and trendy shops. The town of Collingwood on the Georgian Bay is only a 10-minute drive away from the ski resort.

Blue Mountain and Collingwood are also great destinations for a summer Ontario day trip. When you’re visiting with kids, be sure to purchase the Play All Day Pass, which will give you access to over 10 different attractions including a mountain roller coaster, a canopy climbing net, ziplines, and more.

Suggested trips: Between Collingwood & Toronto: Smartphone Audio Driving Tour

Algonquin Provincial Park

Located between the Georgian Bay and the Ottawa River, Algonquin Provincial Park is a natural wonder worth a visit in Ontario. The park is huge, to say the least, with over 2400 lakes and miles worth of streams.

Driving from Toronto to the entrance of the park will take just under three hours, but once you’re there, you could spend a lot more time driving between the different attractions. While it’s a great park for a day trip, Algonquin has been praised for having some of the most beautiful campsites in Ontario . Take what you want from that!

You have to pay for a permit to enter the park, so make sure the tour you pick includes entrance fees in the day rate. An outdoor lovers’ playground, Algonquin Park is a hotspot for recreational activities. From backcountry camping to boating, canoeing, dog sledding, fishing and hunting, picnicking, skiing, snowmobiling, and swimming, there is something to do all year round in this exquisite area.

Suggested trips: Algonquin Provincial Park Day Tour , 6 Hour Algonquin Park Canoe Trip , and Algonquin Park Winter Adventure

St Jacobs 

Located just outside of Waterloo along the Conestoga River, only an hour and a half drive from Toronto, The Village of St. Jacobs is a charming spot to visit for a cultural day trip in Ontario.

If you’re up for some local history, St. Jacobs has a unique Mennonite heritage . The town was first settled in the early 1830s by Pennslyvania Dutch populations. The heritage of the village has been well preserved – you can even still visit the first mills built in the area! St. Jacobs had a small population with a strong Germanic culture, which is still evident today. 

Walking through the streets feels like you’ve taken a step back in time. But today, the streets are lined with trendy boutiques, specialty stores, and antique spots. Don’t forget to check out the Farmers’ Market, which is a big drawing point in the village. It sells everything from artisanal to home-baked goods.

If you want to extend your day trip to an overnight one, spend a night in this classic 1842 B&B with village views. 

Port Dover 

Known for its bustling fishing industry, Port Dover is a small town located in Norfolk County on the northern shores of Lake Erie in Ontario. Today, this lakeside village is well-loved for its beaches, piers, and local community, making it a great stop for an Ontario day trip.

If you’ve never been to Norfolk County, Port Dover is the place to start exploring. Named after the town of the same name in England, it was established in the early 1800s. The village was burned down and rebuilt, and has since developed a name for itself as one of the largest freshwater fishing areas in the Americas.

Boaters will love the Port Dover Harbor Marina, while foodies will be kept busy by the restaurants along the lake shores. If you happen to visit on a Friday the 13th, you’ll be greeted by lines of motorcycles that parade through the streets. 

The village is about a two-hour drive from the city of Toronto. If you feel like exploring more of the area, rent out this charming waterfront cottage outside the city.

Ferris Provincial Park 

Ferris Provincial Park is another outstanding nature-lovers paradise on the doorstep of Ontario’s big cities. Just like Algonquin Park, Ferris is a top destination for overnight camping, but being only two hours from Toronto, it’s also a great spot for a day trip.

There are a ton of adventurous things to do in the park. If you visit during the fall months, you’ll be blown away by the colorful trees from the lookout over Ranney Falls. Spring is just as gorgeous, when the park shows off brightly colored wildflowers along the Drumlin Trail. In winter, you could backcountry ski and enjoy the snowshoe trails which are well maintained by park rangers.

Summer is the best time for enjoying time on the Trent River. Whether you enjoy kayaking or prefer admiring the bird and wildlife from the shore, there’s something for everyone. Don’t miss the pedestrian suspension bridge over the Trent River Gorge, which overlooks exquisite panoramic views of the park.

Fancy spending some more time in the park? This quaint cottage Airbnb in Campbellford has everything you might need for a short stay.

Suggested Trips : Rail Town Off-Road Quad Adventure

The Stratford Festival 

A short two-hour drive from Toronto, Stratford is a small city on the Avon River in Ontario’s Perth County. Just like the Stratford Upon Avon in England (which was home to the Great playwright Shakespeare), Ontario’s Stratford was also settled by English, Irish, Scottish and German immigrants in the early 1800s.

The city is best known for its selection of top-rated restaurants, its art scene, and its festival season which runs from May through to October. When you visit during these months, you can plan your trip around the Stratford Shakespeare Festival or the Stratford Summer Music Festival. Trust me when I say, these festivals are worth a visit, and they are the city’s claims to fame.

That being said, it’s a spectacular place to visit on a day trip from Ontario year-round, with a charming small-town atmosphere, outstanding dining options, and a fascinating history rooted in English literature, theatre, and western culture.

Suggested trips: Stratford Countryside Dining Experience

Prince Edward Wine County

More wine tours? We like the sound of that! Thanks to its limestone-rich soil and moderate climate, Prince Edward Wine County is home to some of the most famous Canadian wine producers.

Just over two hours from the city of Toronto, the county plays host to over 35 independent winemakers, each using different wine-making techniques to create uniquely tasty craft beverages. Unlike many other wine tasting trips, winetasting in Prince Edward is refreshingly unpretentious and offers a more down-to-earth experience than most.

Most of the wineries in the region specialize in Pino Noir and Chardonnay, but the local winemakers are always learning new tricks and testing new techniques. It’s not all about wine here, though, and you could also make a stop at the local brewery for a cold one, or wander through the local farmers’ market and museums until your feet give in.

Suggested trips: Tesla Wine Tour and Horseback Adventure at Fina Vista Farm

The Muskoka Lakes and Gravenhurst

Muskoka is a collection of eclectic towns and villages about two and a half hours drive from Toronto. Together with over 1600 lakes, a vast forest, and a bunch of great restaurants and bars, it’s no wonder Muskoka is such a desirable destination for an Ontario day trip.

In fact, when you’re visiting this area, you might bump into Tom Hanks, Justin Bieber, Kate Hudson, or Steven Spielberg, who all allegedly have cabins on the lake shores! While the best time to visit is definitely during the warmer summer months, the lakes and their surrounding trees put on a spectacular show of oranges and yellows during fall too. 

Suggested trips: Barefoot Earthing Experience and Canoe Fishing Guide

Wasaga Beach 

Wasaga Beach is a great spot for a day trip if you want your own adventure, without the hassle of organizing a tour. The beach is only an hour and forty-five minutes from Toronto, and is the world’s longest freshwater beach. With pristine white sand and panoramic views of the Niagara Escarpment across the Georgian Bay, it’s also one of the most beautiful!

If fishing is your thing, the Nottawasaga River nearby is excellent for game fishing. You can rent a boat or canoe and explore the area. Go golfing, skydiving, hiking, biking, or even snowshoeing and cross country skiing during the winter months. The activities are endless no matter what time of year you choose to visit!

Mount St. Louis Moonstone Ski Resort 

Ski and snowboard trips are so nice, we had to add them twice! Mount St. Louis Moonstone Ski Resort is only an hour and a half from the city, making it perfect for a winter day trip. 

About half the terrain is groomed for intermediate skiers and riders, while 35% is appropriate for beginners. If you’re after the hard stuff, 15% of the terrain is categorized as difficult.

There is a well-equipped snow school and rental shops which will keep young kids busy all day. If you’re a confident skier or snowboarder, you could try a run down the park and pipe (locally known as the Skool Yard, Junkyard, and Outback) for a kick of adrenaline. 

A day out in the snow can get exhausting, but there is a spacious cafeteria at the base of the mountain where you can grab a hot chocolate or bite to eat for a quick refuel at any time. You can make this an overnight trip with a stay in this cozy villa with a jacuzzi and private parking.

Wanna know how to pack like a pro? Well for a start you need the right gear….

These are packing cubes for the globetrotters and compression sacks for the  real adventurers – these babies are a traveller’s best kept secret. They organise yo’ packing and minimise volume too so you can pack MORE.

Or, y’know… you can stick to just chucking it all in your backpack…

Don’t Forget Your Ontario Travel Insurance

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

Ontario is one of those spread-out provinces that has so much to offer. The majority of tourists spend their time in the big cities. However, when visiting a city like Ottawa or Toronto, it’s always important to spend some time checking out the areas beyond the skyscrapers and highways.

Taking a day trip from Ontario and exploring the beautiful nature that the province has to offer will be the highlight of your trip. From pristine lakeside beaches to cozy winter ski resorts to exquisite national and provincial parks, there is so much more to do in Ontario than first meets the eye.

The Prince Edward Wine County is a personal favorite of mine, however, the convenience of seeing Niagara Falls and the Niagara Wine Region in one day is ideal for those without much time to spare.

And for transparency’s sake, please know that some of the links in our content are affiliate links . That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!

Sheridan Cahoon

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TRAVEL. TASTE. SIP. FIND. GO!

tasty road trips

taste adventures

Tasty Road Trips has curated several ‘planned-for-you’, all-inclusive daytrips where friends, international travelers, and corporate guests/teams can connect through authentic taste adventures in Ontario Canada. We embrace small-towns, on farm experiences and want to share their big bold beautiful tastes, with you!

Click through the tours below to choose your local tasting adventure.

Explore Paris Like A Local - A Sweet Escape

A custom curated all inclusive, self-guided walk & taste experience in charming downtown Paris Ontario, which includes:

Custom timed itinerary, just for you

All food reservations made for you

Recommended best shops, geared for your day

Five + delicious taste locations

VIP art gallery visits, with a studio tour

Scenic views & best photo opps in Paris

Culture and history points of interest

Nature walks in case you arrive early, or want to stay late

Tasty Road Trips Exclusive Market Bag, as your ID for the day.

You will not be hungry at the end of this daytrip walking adventure! I promise you, Spicy Jan.

Your exclusive Tasty Road Trips Itinerary will offer a history of the town, scenic views, must-visit shops & boutiques, the coolest art galleries, and the best selfie locations.

Tour Details: This tour is a 4.5 hour all-inclusive self-guided tour with all food, sips, and gratuity included for your day.

A Taste of Norfolk

Prepare yourself for this all-inclusive self-guided driving experience, enjoying delicious food and beverage tastings, and on-farm experiences while cruising along the Lake Erie shore. This tour includes:

Custom timed itinerary, with all the delicious detail just for your group.

Enjoy a leisurely afternoon discovering Rural Ontario, Port Dover, Scotland, Normandale, and St. Williams – some of the best sips and bites this region has to offer.

More than 5 local taste & sip locations

Scenic views & best photo opps along the shore

You will not be hungry at the end of this daytrip #roadtrips adventure! I promise you, Spicy Jan.

Tour Details: This tour is a five+ hour all-inclusive self-guided driving tour with all food, sips, and gratuity included for your day.

Home of #99 Taste Adventure

On this Brantford & Brant, all-inclusive self-guided driving adventure, you will eat, shop, explore, discover and sip where the locals enjoy. Brantford is the hometown of Wayne Gretzky #99, and Spicy Jan will make sure you see the best local hidden gems the area has to offer. Your tour includes:

Curated itinerary of unique destinations where you will fill your market bag with local sweets, treats, and enjoy some Farmers Market Tastings.

Spicy Jan guaranteed, you will be grazing from am to pm and love every delicious stop. You will not be hungry on this daytrip.

Visit to a local farmers market

Tour Details: This tour is a five+ hour all-inclusive self-guided tour with all food, sips, and gratuity included for your day.

Road to the Ridge: Tastes of the Escarpment

This custom curated self-guided driving experience will bring you along the magnificent escarpment overlooking Stoney Creek and Ancaster. Your tour includes:

Breathtaking views of the rural roads on the Hamilton Mountain

Wine, lunch, a stop at the local market (seasonal), and grazing the day away in beautiful Stoney Creek and Ancaster

Cheese Shop Tasting Experience

Scenic views & best photo opps throughout your day

You will not be hungry at the end of this daytrip adventure! I promise you, Spicy Jan.

A Taste of Paris - Sip, Savour & Shopping

A custom-curated all-inclusive self-guided walking experience that explores downtown Paris with all the must see and do suggested stops while in town. Included are three tasting stops, and details of the nearby nature trails & waterways which surround the downtown Paris core. This tour includes:

Custom timed itinerary, with all the delicious detail

One light lunch and sip destination

One sweet stop to get your sweetness going wild!

Sip sip away, in this on trend cafe – it’s on us!

Recommended shopping experience to maximize your day.

Recommended must visit art galleries are on this tour

Scenic views, nature trails & the best photo opps in Paris

Tasty Road Trips Exclusive Market Bag as your ID for the day

Tour Details: This tour includes three tasting locations with timed stops to make your day satisfying and still have lots of browsing around town time. Reservations will be made for you.

‘To Market We Go’ - Brantford & Brant

Market Lovers who love locally inspired great tastes … this is for you!

On this road-trip day-trip self driving experience, you will visit several unique local markets which are all deliciously different. This is a full day tasting experience through Brantford, Brant and Paris.

Curated itinerary of unique destinations where you will fill your market bag with local sweets, treats, and savory bites – this is what markets are all about!

From cheese to Latin food, to farm-fresh, and more, this multi-market experience will not disappoint those who love a true local road trip.

Recommended best shops and hidden gems, geared for your day

On this culinary adventure you will be grazing from am to pm and love every delicious stop. You will not be hungry on this daytrip.

Tour Details: This Tasty Road Trips Tour is a full-day trip experience with a customized itinerary. This is a Friday and Saturday tour only.

Mystery Taste Adventure

A mystery tour curated by Spicy Jan herself and you have to be willing to go anywhere in Hamilton, Halton, and Brant Regions!

It’s a Mystery Road Trip Itinerary you won’t find out about until 3 days before your date!

Only Jan knows your locations and if you know Spicy Jan… she loves great places to explore and dine! Get ready and you need to have faith for this one!

Corporate - Team Building

Are you looking for the best way to engage your teams in social engagement outside of the office. Are you a leader looking to inspire that team spirit in your staff, yet with an interactive hands-on experiential theme. Tasty Road Trips has you covered.

We have curated the best way for your team to work together to find clues to delicious interactive destinations. We would love to host your group in Paris Ontario and bring you the best small-town team building experience, that will keep your department coming back for more.

We build community through multi-sensory experiences, they will remember for years!

Tastings and lunch included. Half Day Hands-on team building experience. Option to be held in person in Paris or Brant.

Private Group Tours

Book your deliciously curated custom group tour today. We offer private group tours in all Southwestern Ontario, for a minimum of 6 guests. All tours include:

Private driver and vehicle for your outing adventure

All food and drink reservations curated for your group

All gratuity included

Tour Details: This tour is a full-day, 5 hour all-inclusive self-guided tour with all food, sips, and gratuity included for your day.

Please click below to send Jan the details and location you would like for your tour, and we will custom create a delicious day out for your group!

Historic Downtown Cambridge

A custom curated all inclusive, self-guided walk & taste experience in charming downtown Cambridge Ontario, which includes:

Five local taste locations

Scenic views & best photo opps in Cambridge

$125.50 per adult + HST

The Paddle & Taste Adventure in Paris,ON

Spicy Jan custom curated this daytrip adventure for those who want to experience it all!

Your day begins with a 2-hour leisurely paddle experience on The Grand River.

For the afternoon, Spicy Jan arranges a delicious local lunch destination for you with your choice of beverage, cappuccino, kombucha … you decide . Plus, we make your reservations so you will never have to wait in line.

The rest of the afternoon is a custom-curated self-guided walking experience in Downtown Paris with more great locations to visit, indulge, and shop all included! You will not be hungry at the end of this day!

Start times are between 10 & 11 am (pending availability)

All reservations and itinerary details to be coordinated by the Tasty Road Trips Team.

You will receive an exclusive itinerary for the day with all the details four days in advance of your experience.

Experience day All-inclusive with Turbo Tube – $110.50/person + HST

Private Group Tours & Virtual Events

Inquire to request a private tour experience for your group, team building, conference delegation or virtual event.

Tasty Road Trips is recommended by the Ontario Culinary Crew!

Click here to view the article

Arlington taste Adventure

Exclusively curated for the Arlington Hotel-Paris , this Grand Adventure Scavenger Hunt offers a delicious way to discover some of the great tastes & scenic views in downtown Paris… but first you have to find them all. 

Book the Adventure Package and stay overnight at the Arlington Hotel and receive a Scavenger Hunt Box or visit the front desk any day of the week to purchase an Arlington Grand Adventure. 

And yes, there is an awesome weekend package prize up for a win!

Contact the Arlington Hotel-Paris below or book directly on their website to secure your overnight stay or adventure for the day.

1+ 226-227-1767  |  info@arlingtonhotel.ca

• Give Us a Call 226-802-0486
• moc.s 1714199736 pirtd 1714199736 aoryt 1714199736 sat@n 1714199736 aj 1714199736

30 Best Ontario Road Trips You Need to Experience (2024)

Posted on Published: June 27, 2023  - Last updated: January 8, 2024

Categories Blog , Canada , Ontario , Road Trips

These are the best road trips in Ontario that you’ll want to experience as soon as possible. On these top Ontario road trips, I’m going to showcase some fantastic destinations and give you many ideas for upcoming travels in the province. Looking for even more places to visit? Here are the 30 best small towns in Ontario and the best beaches in Ontario .

Spending hours in the car might not seem like a lot of fun at first. However, I’ve got some great road trip tips to help make the journey almost as enjoyable as the destination. Some of the essentials include yummy food and drink (coffee is an absolute must for me!), an epic road trip music playlist, downloadable maps, and don’t forget your sunglasses!

Posts may be sponsored. Post contains affiliate links. I may be compensated if you make a purchase using my link.

Are you a hiker? You may want to hop over to my other website, Ontario Hiking, to check out the top 100 hikes in Ontario . You could easily plan 100 road trips using this list alone. If you’re looking for Ontario road trips with many things to see and do, here’s my list of the best destinations around the province that you simply must see.

Need a Rental Car for your Ontario Road Trip?

I always use Discover Cars when I need a car rental, no matter where I’m traveling in the world. If you’re thinking about tackling any of these road trips in Ontario and you don’t have a car, I suggest comparing car rental prices to find the best rates. Happy road trippin’!

Table of Contents

Best Road Trips in Ontario: 1000 Islands

The Thousand Islands region is an incredible destination for lovers of outdoor adventures. Hiking , kayaking , paddleboarding. You name it and you’ll likely be able to do it in the 1000 Islands. There’s also delicious food and drink, fascinating history, and it’s oozing with small town charm.

The town of Gananoque is considered to be the “gateway to the Thousand Islands”. This is likely where you’ll want to base yourself for the night. There’s a quaint downtown core with shops, restaurants, and even a brewery.

This is also a jumping off point for many popular attractions, like a kayaking tour or a boat cruise of the 1000 Islands on the St. Lawrence River. Then, it’s easy to explore the rest of the region from Gananoque, such as the Thousand Islands National Park . I stayed at the comfortable and conveniently located Colonial Resort & Spa .

Southern Ontario Road Trips: Grand Bend

Grand Bend is home to one of the best beaches in Ontario , and that’s a good enough reason to plan your Ontario road trip there. Beyond the beautiful beach, there’s also a wonderful provincial park (that also has a pretty beach!), a resort with a spa and golf course, two wineries, and fantastic restaurants.

In this blog post, I show you how to spend a day or two in Grand Bend , while taking a day trip to nearby Sarnia. No matter what you end up doing, don’t miss the sunsets in Grand Bend. They are among the best in the province, Canada, and possibly the world!

If you’re looking for where to stay in Grand Bend, check out Oakwood Resort . Not only is there a spa and golf course, but there’s also great dining options and a pristine section of the beach that you can access straight from the property.

Adorable Towns on Lake Huron

Looking for more great places to visit on Lake Huron? If you continue traveling north from Grand Bend, you’ll hit so many beautiful small towns and villages on the way. Over the course of a weekend or a few days, you can explore each charming place. Stop to admire the little main street villages, the stunning beaches, and the parks and trails.

From Grand Bend and traveling north, the best places to visit include Bayfield, Goderich, Kincardine, Port Elgin and Southampton. You can also continue on to the popular beach town in Ontario, Sauble Beach, with its iconic sign welcoming you to the beach. Stay at a historic inn in Goderich, the Benmiller Inn & Spa , for the ultimate getaway.

Places to Visit in Ontario: Port Stanley

Port Stanley is another one of the best road trips in Ontario that you can take this summer. I recommend visiting both Port Stanley and the nearby village of Sparta, as you can see in my Port Stanley itinerary . Located on the shores of Lake Erie in Elgin County, Port Stanley is one of the cutest small towns in Ontario and an awesome road trip destination.

There are so many things to do in Port Stanley that make for a memorable getaway: shopping, renting a bike and riding around town, having a beach day or two, visiting a lavender farm, frequenting a winery, and even going for a hike. And don’t forget all of the delectable restaurants and coffee shops.

When you visit Port Stanley, I suggest staying at one of the Carriage Houses at The Windjammer Inn . My Carriage House had so many wonderful amenities, like a kitchenette, a Jacuzzi tub, and a little patio out front. Plus, your stay comes with one of the tastiest breakfasts I’ve ever enjoyed at a hotel.

Ontario Weekend Road Trips: Stratford

Stratford is another amazing city in Ontario that has small town vibes, especially around its historic downtown. You might know Stratford best for the Stratford Festival or the fact that it’s the hometown of Justin Bieber, but there are so many things to see in this picturesque Ontario city.

Downtown Stratford has many unique boutiques and small businesses you’ll love. As an artsy city, there’s no shortage of festivities, public art, and local galleries. Stratford is nestled on the banks of the Avon River, so you can soak up beautiful views and explore its scenic trails.

Add delicious food and beverages to the mix, and you’ve got the makings of a delightful trip to Stratford, Ontario. Some of my favorite restaurants include Grounded (“Purely Plant Based Cafe”) and The Planet Diner (vegan comfort food). Spend the night at Foster’s Inn , conveniently located in Stratford’s downtown core.

Road Trip to London, Ontario

London, Ontario is a big city with small town vibes. As I strolled down Richmond Row, the historic shopping district in London’s downtown core, the old buildings seamlessly merged with modern boutiques. It’s also known as “The Forest City”, so you can imagine that there are lots of great outdoor activities in nature.

Here’s why a trip to London is one of the best road trips in Ontario: there are outdoor adventures, fantastic restaurants, brilliant museums, and even a gigantic arcade with tons of video games. I recommend going treetop trekking at Boler Mountain, admiring the thoughtful art displays at Museum London, and playing games at the Rec Room.

For food and drink, sampling tea and eats at The Tea Lounge is a must. Love craft beer? Head over to Curley Brewing Company for refreshing beer and tasty pub fare. Stay at The Park Hotel with its modern and dazzling suites, centrally located in the middle of it all.

Woodstock and Oxford County

Woodstock and Oxford County is another overlooked region of Ontario that I loved visiting. I spent a day in Woodstock and a day in Otterville and Tillsonburg.

In Woodstock, I frequented a lot of amazing local businesses like Early Bird Coffee, Wild Comfort Body Care, Habitual Chocolate, and Upper Thames Brewing Company. One thing that I really loved was how each small business worked with one another. For instance, the brewery provided beer to make body care products. The chocolate shop offered cacao nibs for a stout beer.

Otterville and Tillsonburg were also pleasant surprises to check out. Otterville has lots of opportunities to explore history and nature, and it’s a great place to go kayaking. In Tillsonburg, I cut my own flowers at a local flower farm, attended an outdoor yoga class, and ate lots of yummy food. Combine a trip to Woodstock, Otterville, and Tillsonburg for one of the most epic Ontario road trips.

If you’re looking for places to stay in the region, I suggest checking out this beautiful chalet just outside of Tillsonburg. Stay in this country home in a peaceful setting with many modern amenities.

Road Trips in Southern Ontario: Windsor

Have you visited Windsor yet? It’s one of my top southern Ontario road trips, especially if you are up for an eco-friendly getaway. While Windsor might be known historically as the automotive capital, there are lots of awesome adventures in the city.

I spent the majority of my time in Tecumseh as there are many fantastic activities near Lake St. Clair. You can go standup paddleboarding (I highly recommend the sunset SUP tour). There are lots of cycling paths and trails to explore.

Plus, I loved all of the yummy vegan eats! There’s a vegan donut shop that captured my heart (Plant Joy), especially since you can get your name spelled out in donuts. Also, be sure to dine at Nooch, Healthy Mama, Carrots n’ Dates, and Thyme Kitchen. Stay at A Hidden Gem B&B , a gorgeous historic home in Windsor.

Road Trip to Beaches and More: Turkey Point

Turkey Point is an underrated destination in Ontario and one of the best road trips in southern Ontario. It’s a short drive from Hamilton and Brantford, and just a couple of hours from Toronto. Turkey Point Beach on Lake Erie with its calm waters is a big draw for families with small children, as well as couples, groups of friends, and multigenerational family trips.

If you’re not visiting during the summertime, there are still many great things to do in Turkey Point that can be enjoyed in all seasons. First, Long Point Eco Adventures has thrilling outdoor amusements with its ziplines, kayaking tours, and night sky observation tours. There are also glamping wilderness suites and pods on site.

Justin and I stayed in a cute cottage with some of our friends when we visited Turkey Point. This lakefront beach house is right across the road from the beach, so you really can’t get much closer than this. It’s a cozy beach bungalow with four bedrooms and more than enough room for all your friends and family.

Niagara Falls and Niagara-on-the-Lake

While it might be an obvious suggestion, there’s a reason why so many people in Ontario (and around the world) flock to Niagara Falls . It’s one of the most beautiful waterfalls in the world. Although I’ve been to Niagara Falls more times than I can count, it never ceases to amaze me.

Walk along the Falls, take a ride on the famous Hornblower Cruises ferry to the base of the falls (aka the Maid of the Mist), or walk through tunnels right beside Niagara Falls itself. I have even more suggestions on how to experience Niagara Falls in the fall and Niagara Falls in the winter . The Niagara Parkway is a great place to go cycling , if you’d like a break from all the driving.

Don’t miss going to Niagara-on-the-Lake, especially if you’re a fan of wine. This is the heart of Niagara’s wine country with over 120 wineries to visit. Niagara-on-the-Lake is a charming little town that’s perfect for a day trip, too.

Stay at the Embassy Suites by Hilton Niagara for views of Niagara Falls from your room. If you’d rather spend the night in Niagara-on-the-Lake, we really enjoyed staying at the Pillar and Post Inn & Spa for a romantic getaway together.

Best Road Trips From Toronto: Muskoka Region

There are so many amazing things to do in Muskoka, especially in the summertime. There are kayaking and paddling trips, exploring the hiking trails , or relaxing on a dock with a frosty pint. If you’re looking for places to visit in the Muskoka region, I suggest road tripping through Gravenhurst, Bracebridge, and Huntsville, to name a few.

In Bracebridge, there are numerous waterfalls and natural wonders along the Trans Canada Trail. Gravenhurst is another cute town that you’ll want to explore on the way to beautiful outdoor spaces. Huntsville is a gem of a town with a delightful downtown core, a brewery, and patios upon patios.

Muskoka has approximately 1600 lakes and 14,000 kilometers of shoreline, with no shortage of beautiful beaches and places to explore. You can visit again and again for new experiences each time, making it one of the best road trips in Ontario. It’s also the gateway to Algonquin Park, one of the best provincial parks in Ontario.

Deerhurst Resort is a stunning property in Huntsville to rest your head at night. Justin and I attended a wedding here in the past and the resort was a beautiful destination in itself. There are two swimming pools on site, as well as the spa, a golf course, treetop trekking and much more.

Collingwood, Blue Mountain and Thornbury

You may have made more than a trip or two to Wasaga Beach over the years, but there’s so much more to see along Georgian Bay. Collingwood is a really lovely town to visit with a main street full of shops and restaurants. Scenic Caves Nature Adventures isn’t too far from Collingwood, and it’s home to some intriguing caves and southern Ontario’s longest suspension bridge.

Blue Mountain Village is popular in all seasons, whether you’re skiing or snowboarding in the winter or hiking in the summer. Soak in the soothing waters at Scandinave Spa Blue Mountain or take in an evening lights festival at Blue Mountain, depending on the season.

Continue your road trip west of Blue Mountain to the town of Thornbury . It’s a cute place to visit in Ontario with a main street filled with cafes and shops. There’s also a cidery in Thornbury, a large antique market, and some trails to explore as well. Stay at Penny’s Motel , a chic and stylish property that you’ll love.

Road Trip to Kingston, Ontario

Kingston is another amazing city in Ontario and one of the best road trips from Toronto. Downtown Kingston has charming inns, delectable dining options, and lots of water sports on the St. Lawrence River. Justin and I went standup paddleboarding for the first time in Kingston, and we had a total blast!

There are many Kingston attractions that you’ll want to check out. You can visit historic Fort Henry, take the ferry to Wolfe Island, and tour the Kingston Penitentiary. Lemoine Point Conservation Area is a great place to go for a hike, and going for a ride on the Kingston Trolley Tour is super iconic.

Stay at the Delta Hotels by Marriott Kingston Waterfront to be in the center of all the action. Situated right on the lake overlooking Confederation Park, you’ll be within walking distance of Kingston’s downtown core with its vibrant shops and restaurants.

Tobermory and the Bruce Peninsula

What kind of a “best road trips in Ontario” article would this be if I didn’t mention Tobermory and the Bruce Peninsula ? Tobermory is known as the “freshwater scuba diving capital of the world” for its intriguing shipwrecks in Fathom Five National Marine Park, Canada’s first national marine conservation area.

It’s also home to Bruce Peninsula National Park and its famous Grotto cave. Hikers will absolutely love the Bruce Peninsula as there are incredible trails at the national park, Flowerpot Island , and Lions Head Provincial Park.

Even if you aren’t massively into hiking, there are amazing views for days from the town itself or one of the easier walking paths. In the harbour, you’ll find restaurants and a brewery. It’s a sweet place to visit, although it does get very busy during the summer months. Stay at the Bruce Anchor Motel right in town for a comfortable and convenient overnight stay.

Point Pelee and Pelee Island

Point Pelee National Park is the southernmost portion of mainland Canada, just south of Leamington. You’ll discover five unique Carolinian habitats and the opportunity to witness over 370 species of birds throughout the year.

While I highly recommend visiting Point Pelee by day, you can also have an entirely new experience at night. Point Pelee National Park is one of the best dark sky preserves in Ontario . The best times to see the stars at Point Pelee National Park are during the new moon (when you can’t see the moon in the sky). During these nights, the park will stay open until midnight, which are longer operating hours than usual.

Pelee Island is a great place to rest and unwind. It’s the southernmost inhabited place in Canada. There are a few relaxing hikes, a lighthouse, and a winery. From Leamington or Kingsville , you can also take the ferry over to Pelee Island. Spend the night at Inn 15 Brewery Loft Suites in Kingsville.

Cute Small Town in Ontario: Elora

Is Elora quite possibly the cutest town in Ontario? I don’t like to pick favorites, but Elora really captured my heart . It’s one of the best places in Ontario to visit for the weekend, just an hour outside of Toronto. So, if you’re looking for the best road trips from Toronto, Elora is a great one to consider. Plus, you can visit the nearby town of Fergus in the same trip.

There are plenty of outdoor adventures in Elora, like hiking at Elora Gorge Conservation Area , going tubing, or swimming at the Elora Quarry. Treat yourself to afternoon tea in a pretty garden patio at The Wild Tart. Go shopping along the main street. If you really want to treat yourself, a spa day at Elora Mill is absolutely divine.

Elora also has an assortment of cafes, a brewery, pubs, and restaurants. I suggest spending the night at the cozy Cheshire Cat B&B for a warm and welcoming spot in town.

Dundas, Ontario (Hamilton)

Are you a fan of cute small towns and beautiful nature? Dundas is a community in Hamilton, Ontario that has a little bit of everything. There’s a quaint main street featuring dozens of shops, cafes and restaurants. Don’t miss stopping at Detour Coffee or Beanermunky Chocolates. Go for a stroll at the Dundas Driving Park or attend a local festival in the summer.

Aside from the quaint downtown core, Dundas is best known for its beautiful conservation areas and hiking trails. The  Dundas Valley Conservation Area  is always a treat to visit with its extensive trail system, the Hermitage ruins, and the old Victorian train station. Dundas also has two waterfalls (Tews Falls and  Websters Falls ), as well as amazing lookout point called the  Dundas Peak .

While there aren’t any hotels or apartment rentals within Dundas itself, you can stay down the road in Hamilton. Try the SoMa Furnished Residences for a comfortable and convenient place to stay.

Brant County (Brantford and Paris)

There’s plenty of fun to be had in “The Telephone City”! Brantford has turned into quite the Ontario road trip destination over the years with engaging attractions and museums, including national historic sites, as well as outdoor adventures on the Grand River. You absolutely must go tubing on the Grand River as it’s like a giant natural lazy river!

From Brantford, hop over to the nearby town of Paris, especially if you love small towns like I do. Paris has a charming main street with restaurants and shops. You can dine on the patios lining the Grand River, and there are many Instagrammable spots around town, too. Spend the night at the idyllic Arlington Hotel right in the middle of town.

Prince Edward County

Prince Edward County has grown to be a very popular summer road trip destination in Ontario over the years. Next to Niagara, it’s one of the best wine countries in Ontario, and it’s even home to the world’s first vegan-certified winery, Karlo Estates.

For outdoor activities, Prince Edward County is home to Sandbanks Provincial Park, as well as 800km+ of shoreline to enjoy. There are also six museums around the County featuring Indigenous history and a pioneer village.

Prince Edward County is home to many artists and you can venture out on an art studio trail to visit them in person. Many studios offer instructed workshops where you can get crafty yourself. There’s also so much to see and do when it comes to catching live theater performances or concerts. Base yourself at the Merrill House in Picton and spend a few days road tripping around and adventuring.

Brighton and the Bay of Quinte

Brighton and the Bay of Quinte region is another excellent Ontario weekend road trip you need to take. You’ll find Brighton on the coastline of Lake Ontario, about two hours from Toronto and three hours from Ottawa. This is one of Ontario’s most charming small towns that also has an abundance of outdoor adventures.

There are so many things to see and do in Brighton. You can go hiking at Presqu’ile Provincial Park and Proctor Park Conservation Area . There’s a quaint downtown core with local shops that offer unique finds. Plus, Brighton is surrounded by countryside and farms with the freshest produce around.

In Brighton, the Timber House Resort is one of the best hotels that I’m sure you’ll love. It’s a beachfront property with uniquely decorated rooms featuring wood beam ceilings. There’s an outdoor swimming pool, bicycle rentals, and a great breakfast.

Road Trips in Ontario: Belleville

Belleville is another fantastic road trip in Ontario with many fun attractions and activities to discover. Downtown Belleville features a historic city centre with many local shops, cafes, breweries and restaurants. Check out the street art and colourful murals all over town while you’re there, too.

There’s no shortage of unique seasonal happenings, like Pop-Ups on the Bay, and there are plenty of outdoor adventures to be had. I loved kayaking on the Bay of Quinte and going for a walk on the Waterfront Trail. Glanmore National Historic Site of Canada provides an insightful window into the past, and there might be a cool event to check out when you’re there.

You can pair your trip to Belleville with some other towns in the Bay of Quinte, like Trenton and Brighton. There are also some nearby conservation areas with hiking trails, like Sager Conservation Area , HR Frink Conservation Area and Bleasdell Boulder Conservation Area . Stay at the clean and modern hotel,  Towneplace Suites by Marriott Belleville .

Lennox and Addington County

Lennox and Addington County is a lesser known destination in South Eastern Ontario that you need to add to your Ontario road trip bucket list. Make your home base in Greater Napanee and explore several nearby areas, like Loyalist Township and Stone Mills Township. Stay at the Seasons Gallery Retreat , a relaxing getaway in historic Napanee.

Napanee has a cute downtown core with excellent shops, restaurants and caf. You can walk everywhere in Napanee, including a stroll to a waterfall in the middle of town on a riverfront boardwalk. Then, hop on board a pontoon boat for a cruise on the Napanee River.

Visit one of Ontario’s quiet islands, Amherst Island, perfect for birdwatching and immersing yourself in nature. Stop in the village of Bath first, which is where you’ll catch the ferry to Amherst Island. Bath has one main streets with some artisan shops and a cute coffee shop.

Perth and Lanark County

Have you heard about the Lanark Highlands or the town of Perth ? Make sure you don’t overlook this beautiful region of Ontario as it’s one of the best Ontario road trips. If you’re looking for a getaway in Ontario that offers peace and tranquility, delicious food, welcoming festivals, and something a little out of the ordinary, it’s time to spend a weekend in Perth and Lanark County.

Go for a stroll around Stewart Park, browse the quaint downtown shops, and admire the old architecture around town. You can also try standup paddleboarding or kayaking down the river. If you love hiking, the trails at the Perth Wildlife Reserve Conservation Area are a must.

I spent two nights at the  Best Western Plus Perth Parkside Inn & Spa , which is one of the most popular hotels in Perth, Ontario. Nestled on the edge of Stewart Park, your hotel room may have one of the prettiest views of the town.

Cornwall, Ontario

Have you visited the city of Cornwall yet? It’s Ontario’s easternmost city that sits on the Canada-USA border, located on the St. Lawrence River. It’s the last major stop in eastern Ontario before you enter Quebec. If you’re on a road trip of Ontario, you might consider stopping in Cornwall for a day before continuing on your way.

Cornwall is home to hiking, biking, and kayaking trails at Guindon Park, Gray’s Creek Conservation Area, and of course, the Waterfront Trail. Some of the best attractions include the Lost Villages Museum (a wild story in Canadian history that I’d never heard before!), a spacious city park, and the ruins of a Roman Catholic church that remind me more of Europe than Canada.

Cornwall is full of so many hidden gems that will make you wonder why you never thought to visit before now. Here’s a lovely two bedroom apartment that you can call home during your time in Cornwall.

Best Road Trips in Ontario: Ottawa

Ottawa is an amazing all-season destination in Ontario, whether you decide to plan your summer road trip to Ottawa or visit Ottawa in the winter . There are festivals all year long (Winterlude is perfect for the winter, and you don’t want to miss the famous Tulip Festival in the spring). From ice skating on the Rideau Canal to touring the Parliament buildings, there are so many things that you can only do in Ottawa that make it such a worthwhile destination.

While not entirely in Ottawa, Gatineau Park is the National Capital Region’s conservation park. Most of it is located across the Ottawa River in Gatineau, Quebec. Of course, Gatineau, while not in Ontario, is another awesome place to check out on your road trip to Ottawa.

If you’re a museum buff, you will adore Ottawa. There are seven national museums in total, including the National Gallery of Canada, the Canadian Museum of History and the Canada Aviation and Space Museum. For a spacious and upscale hotel near many museums and the downtown core, rest your head at the Lord Elgin Hotel .

Road Trip Ontario: Cute Towns Near Ottawa

If you’re planning an Ontario road trip of eastern Ontario, there are so many adorable and charming towns near Ottawa that you need to visit. These are some of the cutest small towns that I’ve ever seen. Most of them have picturesque downtown streets where you can walk all over town. Some of them are right on the Rideau Canal, adding even more pretty viewpoints.

While I’ve already mentioned Perth, you can easily road trip to these towns from Perth or Ottawa, depending on the direction you’re travelling from. Drive to Smith’s Falls, Merrickville, Kemptville, Carleton Place and Almonte. Westport is another cute town that’s just south of Perth that you can include on this road trip, too.

I spent the night at the Merrickville Guest Suites , which was a cozy and cute apartment in the middle of town. From there, I was able to walk all over town and it also includes a complimentary parking space (a must for any Ontario road trips!).

Ontario Road Trips: Sudbury

Sudbury might be a four hour drive from Toronto, but it’s well worth the distance. This is one of the best road trips in Ontario for a great combination of city living and wilderness. Sudbury is known as the “Nickel City” for its mining history and the “City of Lakes” for its 330 lakes. In fact, Sudbury has more lakes than any other city in Canada.

Sudbury is the perfect place for outdoor adventures, visiting unique and popular tourist attractions, and wandering around a bustling city centre. It’s northern Ontario’s largest city and there’s no shortage of awesome attractions and activities. Check out Science North, the “Big Nickel” and Dynamic Earth.

For hiking trails and waterfalls, make some room in your itinerary for Lake Laurentian Conservation Area, Kivi Park, Onaping Falls and the A.Y. Jackson Lookout, and Bell Park / Ramsay Lake. Public art lovers will adore Sudbury – it’s home to Canada’s largest mural, as well as numerous other colorful works of art throughout downtown Sudbury. I stayed at the Hilton Garden Inn Sudbury , which was the perfect place to relax after days of adventures.

Killarney and Killarney Provincial Park

If you continue for another hour beyond Sudbury, you’ll discover one of the most beautiful places go to go hiking in Ontario. Killarney Provincial Park is home to the “Crack” trail , which leads to a stunning panoramic lookout point. Killarney Provincial Park has some less challenging trails across the rocks of the Canadian shield, as well as some lengthier trails that take several days to hike.

The town of Killarney is very small and there are only a couple of places to stay in town that are destinations in themselves. It’s one of the prettiest scenic drives through the grounds of the provincial park to reach Killarney. We spent a couple of nights at the Killarney Mountain Lodge where you could dine at the on-site restaurant or relax in the Muskoka chairs by the waterfront.

I suggest making a larger road trip journey where you visit Sudbury for a few days, and then venture down to Killarney Provincial Park for a couple more days. You can even extend your trip for longer and drive to my next suggested place for a road trip in Ontario…Manitoulin Island!

Manitoulin Island

Manitoulin Island is one of the most amazing road trips in Ontario, whether you drive there or take the ferry from Tobermory. It’s the largest freshwater island in the world, situated on the shores of Georgian Bay and Lake Huron.

Take a tour with the Great Spirit Circle Trail for an amazing Annishanabe cultural experience, learning more about the customs and legends of the local First Nations Peoples. Visitors are also welcome to the annual Pow Wows hosted by each First Nation community on Manitoulin Island.

Manitoulin Island is a paradise for nature lovers and outdoor adventurers. You must hike the Cup and Saucer Trail, and a stop at Bridal Veil Falls is a must. It’s even possible on some nights to see the northern lights from Manitoulin Island, as it’s one of the best dark sky preserves in Ontario . Stay at the Manitoulin Inn for a comfortable home base between your adventures.

Best Road Trips in Ontario: Thunder Bay

Thunder Bay is one of the most amazing places to visit in Canada, a dynamic city surrounded by rugged wilderness. While it’s quite the drive from southern Ontario, it’s well worth the journey (or you may wish to fly to Thunder Bay and rent a car when you arrive , like I did!). There are so many things to do in Thunder Bay, both in and around the city, especially if you love exploring the great outdoors.

Perched on the shores of Lake Superior, the world’s largest freshwater lake, the city of Thunder Bay is the gateway to some of Canada’s most epic landscapes. Northwestern Ontario is home to 150,000 lakes and an ancient Boreal forest with over 44 billion trees. Go paddling or venture across the vast Canadian Shield on foot.

Though it’s wonderful to explore the shops and restaurants in downtown Thunder Bay, the main attractions lie in the nature on the outskirts of the city. Explore Sleeping Giant Provincial Park (hike to the Top of the Giant), walk across Canada’s longest suspension bridge at Eagle Canyon Adventures, witness a vast gorge at Ouimet Canyon Provincial Park, and see the “Niagara Falls of the North”, Kakabeka Falls.

Spend the night in Thunder Bay at The Courthouse Hotel , a 40-room boutique hotel in the former Superior Court of Justice building, dating back to 1924.

Lauren is the full-time travel blogger and content creator behind Justin Plus Lauren. She started Justin Plus Lauren in 2013 and has travelled to 50+ countries around the world. Lauren is an expert on vegan travel as one of the very first vegan travel bloggers. She also focuses on outdoor adventure travel, eco and sustainable travel, and creating amazing travel itineraries for cities and small towns.

Surprise Getaway from Toronto – Guess Where Trips | Ontario Review

Have you ever wanted to just plan a getaway from Toronto for a day? Or have you ever wanted to plan a surprise trip for your partner? And have you ever suddenly decided against taking that getaway because:

• it was a long week and you just don’t have the energy to plan that getaway
• you want to go *somewhere*, but not enough to actually research places to go for it
• you’re bored of your own local travel ideas (I get it, some days I don’t really want to go hiking, but I can’t think of anything else to do either!)
• you feel like you already know what all of Southern Ontario has to offer

then you might want to consider trying one of the curated itineraries created by Guess Where Trips.

Disclaimer: SYDE Road was not sponsored or commissioned to create or update this post – we bought the services on our own and we’re giving our honest review of our own experience.

Looking for other day trips near Toronto? Here are some posts you may like!

• Hike on one of the prettiest trails in the Dundas Valley
• Visit this European themed Village Square in Burlington
• Drink some hard cider and wine at this super dog-friendly, dog themed Winery in the Norfolk County

Surprise Getaway from Toronto – Guess Where Trip Review Contents This post is lengthy. Here are some links to jump to the content you’re looking for. Enjoy!

Last Updated: October 9, 2021

What is Guess Where Trips?

Guess Where Trips is an Ontario-based company that produces curated itineraries around Canada that are

• theme-based
• self-guided and
• day-trip friendly (with options to make it overnight!)

all for $55 . The kicker? All the road trips don’t tell you the destinations! Every itinerary is essentially a mystery road trip somewhere in Canada.

Need a bit of convincing? Check out this quick summary from our second Guess Where Trips!

@syderoad I don’t know who Keith is but well done 🎉 @guesswheretrips #guesswheretrips #surprisetravel #travelontario #surpriseroadtrip #mysteryroadtrip ♬ Lonely – Airliftz

Guess Where Trips Locations

At the time of publishing, the company currently offers surprise road trips that start from: Calgary , Halifax , Toronto , Ottawa , London , Windsor , Winnipeg , and Vancouver .

The list continues to be improved upon and added to, so check back on their website for new getaways!

For today’s post and review, I will be focusing on the road trips offered in Ontario … because well that’s where I live!

The dog-friendly adventures are highlighted in green below. While most of the available getaways are labelled as dog-friendly, some of the itineraries may have restrictions at food places or specific stops.

If you’re not certain about an itinerary, you can definitely contact Guess Where Trips to make sure that the itinerary is 100% dog-friendly.

Guess Where Trips around Toronto:

• Wine Time and Hidden Gems – Look to the East of Toronto. Includes an iconic market, a scenic boardwalk, some quirky & cute wineries, a ‘Ghost Town’, and a few hikes along the way.
• Weird & Wonderful Things – Head North of Toronto. You might sightsee waterfalls, go on hikes, go through a town with hidden outdoor art, and visit a place ranked as “one of the world’s most bizarre places”.
• The Waterfall Route – Head north and escape the Hamilton waterfall road trippers. Discover new waterfalls, scenic views, new small-town food shop favourites, and a one-of-a-kind seasonal garden
• Historic Haunts – Get spooky driving West of Toronto. Visit haunted schools, post offices, hikes, graveyards, ghost towns, and several other locations with a haunted past.
• The Butter Tart Trail – In the mood for butter tarts? Take this surprise road trip and head East of Toronto to enjoy some country farms, country bakeries, picturesque historic buildings and ruins, and some cottage country towns all while devouring as many butter tarts as you can!
• The Fairy Tale Trail – Live in the GTA, Niagara, or Kitchener-Waterloo area with kids under 12? This is the ideal mini road trip to complete with your children. Transport your child and let their imagination run wild as you visit waterfalls, castle grounds, and wildlife in this stroller-friendly road trip.
• The Whimsical Route – Another mini road trip designed for families with children over the age of 5 that live in the GTA, Niagara, or Kitchener-Waterloo area. This trip will take you on a number of easy outdoor adventures that provide a variety of kid-friendly options at each stop. There’s even a scavenger-style activity throughout the itinerary to keep your kids engaged!
• Bridges to Beaches – Look to the North-West of Toronto for hikes, pretty beaches, a seasonal waterfall spot, and maybe some alpacas and goats too! You’ll love the bridges in this itinerary that are perfect for a photo-op too.
• Taste of the Country – Discover scenic towns, do a waterfront photo op, and enjoy some cute, family-friendly farms when you head west of Toronto on this road trip!
• Funky Florals and Fine Wines – Head to the regions South-West of Toronto. The itinerary might bring you through a floral wonderland, wineries, and a cute Canadian Town.
• Local Markets & Picturesque Towns – Drive West of Toronto. Includes historic towns with great local markets, a picturesque surprise stop, beautiful gorges and riverside walks, and stopping at “the most beautiful village in Canada”.
• Outdoor Adventures – Head North-East of Toronto to get away from the crowds. Go to a cute town with a few surprises, take a short hike, visit an Italian winery, and ogle at some pretty countryside driving

Guess Where Trips around Ottawa :

• Brews, Bites, and Everything Nice – Explore the South-West regions of Ottawa. Enjoy a couple of adorable cafes and shops. Stroll through a variety of different breweries & distilleries, and maybe take a few photos as some of the spectacular photo opportunities in this itinerary
• Quirky Adventures – Go South of Ottawa for this adventure. Maybe visit adorable towns, look at beautiful views at a boardwalk, see some old mill ruins, and drive-by a very cool photo opp. You might even have some forest bathing opportunities too.
• Local Wonders – Discover some hidden gems within the city’s limits! Look forward to some insta-worthy photo ops, funky restaurants, and some classic treasures you might just have forgotten about!
• All the Pretty Things – Looking for stunning viewpoints, delicious restaurants and wineries? Then check out this surprise road trip itinerary!
• Views & Secret Stops – Look for an underground tunnel south of Ottawa. Then, go on scenic hikes, visit a craft cidery, a waterfront town, and head to numerous viewpoints and photographic opportunities with this itinerary.
• Backroad Bliss – Perfect for folks who live anywhere between Ottawa and Montreal! This secret travel itinerary takes you from waterfalls and hikes to ridiculously cute towns and shops. There’s a little bit of everything to be enjoyed on this trip!

Don’t Peek! Your destinations are sealed!

I love that Guess Where Trips mails you the itinerary in several sealed envelopes . How cute and unique! Like the company’s name implies, you really only find out where you’re going once you get to each stop in the itinerary.

The package includes:

• a ‘before you go’ envelope that gives you all the details you need to know about your day trip (spoiler-free details!)
• several numbered envelopes

Each getaway , including driving time, is generally 6-8 hours long so you’re definitely in for a full day of adventuring regardless of which adventure you choose.

What you get when you buy Guess Where Trips

What does the $55 include.

When you purchase a Guess Where Trips itinerary you get the following:

Note: as of June 2, 2020, Guess Where Trips rebranded and upgraded the experience. You’ll still receive the sealed envelopes, but they’re coming in redesigned envelopes and instead of pamphlets, they’ve been upgraded to super pretty booklets !

• Detailed before you go pamphlet
• A planned itinerary with recommended driving hours and destination hours
• Recommended breakfast/café and lunch locations
• Optional stops in each itinerary
• Updated information on travel restrictions to destinations (including any restricted weekend or weekdays due to business operating hours)

What is not included?

The Guess Where Trip services do not include :

• Costs incurred for going on the getaway itself including gas, food, drinks
• Admission fees to the suggested locations in the itinerary

Guess Where Trips Reviews – Our Experience (spoiler-free)

I started guessing a few weeks before we went.

The surprise and anticipation of a Guess Where Trip can begin way before your trip if you plan it outright. For me, the guessing experience started several weeks before we even started the trip. Out of the blue, Angelo asked me to block a full day off for an extra special date.

It doesn’t have to be any special day… we can do it whenever, but it does need to be a full day. Oh and wear comfy but cute clothes. Angelo being tightlipped when I asked where we were going

Talk about mysterious! So here’s the thing about me. I love guessing things. I love guessing movie endings before starting a movie, guessing where we’re going and even guessing my birthday or Christmas gifts before I get them. I love it so much that Angelo has had to impose a ‘guess 3 times only’ rule to keep me from talking his ear off! Having a very tightlipped partner meant that I wasn’t going to get any more hints.

Hmm.. since he said that ‘ it doesn’t have to be any particular day ‘ that probably meant it wasn’t holiday-related, concert-related or any special event-related activities like Rib Fest. But the full-day part really got me thinking… alas, I really didn’t have much to go on!

Maybe a winery somewhere? Or a hike at one of the provincial parks? Hmm but the ‘comfy AND cute’ part doesn’t seem like it could be a hike either (I don’t own ‘cute’ hiking clothes.. they’re all sweats!). I was stumped!

Revealing the Surprise and Receiving the Package

A few days later we received a non-descript brown package in the mail. It was just large enough to hold a book. Turns out the package was for the full day date! Now my thoughts were racing. Maybe we were going to a concert after all? Hmm but this was October 2020, during COVID restriction times, there’s no way there’d be a concert right now. Something that only the two of us could do… Maybe it was one of those date book ideas and we would spend the day going through it? I was still stumped.

By now, we had already decided on a date and my not-so-discreet search attempts on the Internet for upcoming events resulted in.. no answers. I was still doing to have to wait and find out what we were doing.

My project manager tendencies were really itching. I needed to make a plan for our date, but I couldn’t .

I’m not opening this until the night before. No more guessing. Angelo to me when I tried to exceed my 3 guess limit

Finally the reveal

The night before our scheduled date night had finally arrived.

We opened the mysterious brown package. I was finally going to find out what we were doing. Imagine my surprise when I found out we were doing a getaway from Toronto and that Angelo, the one who ‘planned’ this date, didn’t know what we were doing either!

All he knew was that we were in for an interesting and possible weird experience – he bought Guess Where Trips’ Weird & Wonderful Things for us to try out. I LOVE weird and quirky things so I literally could not wait to head on out and do this trip! Alas, I needed to wait one more night before I could 🙁

We read the ‘before you go’ envelope and followed the instructions. We packed some money and picked out some clothes for our date. It was pretty clear that we would be driving for a while. There was also something about donating a can of goods at one of the locations… but ironically enough we didn’t have any canned goods in our house that day, so we made a mental note to stop by somewhere on our date day.

Our Trip Experience

To keep the experience as spoiler-free as possible – this part is purposely going to be vague. We started our day off early-ish at about 9 AM, stopping by McDonald’s for some breakfast. The itinerary listed out several cafes for the day but as they were an hour or so away, we figured that eating breakfast first and then stopping at the cafes to enjoy a coffee would be better for our hunger.

Our itinerary took us north to a cute town with a unique café. We weren’t able to linger at the café because of COVID travel policies and drank our coffee outside. Unfortunately because of this, we weren’t really able to appreciate their unique interior design for more than a few minutes as we waited for our coffee to brew.

At this point, we met a family of four who also stopped by this cafe. As they bought their cookies and headed back to the car, we noticed they were clutching the same Guess Where envelopes as us! So as you go on these itineraries, keep your eyes peeled as you may see fellow Guess Where adventurers around you too!

Next, we stopped at a cute town (not pictured to keep things spoiler-free!) with a waterfall before opening our next envelope. We entered the address into our GPS and away we went.

Our next stop took us to a populated scenic viewpoint of the area where we got to enjoy the fall colours the area had to offer. The envelope did mention that this particular location was a perfect place to enjoy a lunch break, but we decided to stop by one more optional hike activity before trying one of the three lunch places offered in the itinerary.

To be honest the optional hike was gorgeous! We liked this hike better than the waterfall listed in the main itinerary. It was a slightly secluded, tall, and beautiful waterfall nestled at the end of a short trail. We had the option to head to the top of the falls as well as enjoy a short walk to the falls’ bottom. There was practically nobody there and it felt like we had the falls all to ourselves that day.

Afterwards, we went for lunch at one of the recommended locations, and again due to COVID restrictions, we had to get takeout and eat it outside, but the food was delicious. At this point we needed a canned food donation, so we stopped by a gas station to pick one up before heading to our last and final stop, an outdoor park.

To be honest our last stop at the outdoor park was our favourite location and it pains me so much that sharing any additional photos will immediately reveal the location and give away the surprise. Our Guess Where Trips itinerary truly saved the best for last and I really wish they allotted more time for this last stop. We arrived at this area by the late afternoon/ early evening and honestly, we could have spent an extra hour here if we could!

Was the trip worth it?

The short answer? Yes. We LOVED that we there is a service that takes the planning out of day trip. Something about opening a sealed envelope to reveal directions to your next destination is SO SATISFYING. I love it so much that I might even be tempted to re-create something like this next time I plan a day trip for ourselves!

For $55.00, Guess Where Trips takes the planning out of the trip and fully allows the entire party to enjoy the trip with minimal planning. Overall we found the itinerary to be:

• accurate with estimated driving times
• accommodating – offering several meal options to cater to dietary restrictions or cravings
• flexible – since this is self-guided you can stay at each stop for however long you’d like and pick and choose the optional items to best suit your day needs
• dog-friendly – we didn’t try this with Limone since it was a humans-only date day, but after going through it, we’d love to try a new experience and bring Limone to the other dog-friendly options!

What I like the most about this service is that everyone on the trip gets to experience the joy of guessing where the next location will be and reacting to the place once we get there.

The price tag isn’t even a per-person experience – it’s the cost of each itinerary, meaning you’re not restricted to the number of people you take to experience it. Next time, I’d really love to do this again and bring Limone and my friends and family with us too!

[Update: October 9, 2021] Surprise surprise! We loved it so much we bought one experience for our relatives and bought another to experience for ourselves again!

Two years later, we went on another fall road trip around Ontario with Guess Where Trips. Our verdict? Still freaking awesome! Other than the updated packaging and added itineraries, the heart and soul of Guess Where Trips remains the same. Guess Where Trips continues to consistently curate and deliver itineraries that:

• are educational
• are fun to explore
• support a plethora of local businesses
• inspire and prove that local travel can be just as exciting and fun as international travel

My verdict remains the same! 100% recommend trying at least one trip, if not several! I promise you’ll discover some new hidden gems that you’ll love!

In the theme of keeping things a surprise, I won’t be listing out any locations for updated Guess Where Trip pictures – but feel free to enjoy our new photos 🙂

So what do you think? Will you give Guess Where Trips a try as well? If you did, I’d love to hear your experience of the trip as well!

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Mystery Trips: Going No One Knows Where

Mystery Trips: All the Fun, None of the Hard Work, No Idea Where You’re Going

By Samantha Butts

Oftentimes planning a trip is the most grueling part. You have to research places to stay, eat, and visit.

This part isn’t always bad, but sometimes it would be nice to not have to worry about all the details of your trip. Planning a vacation has become a long and often difficult process to do alone.

Travel agencies and tour companies are great for organizing trips with ease. However, there is a more exciting option that requires almost no planning on your part: mystery trips.

Mystery trips are not only planned for you, but they also create a sort of suspense for the traveler. For the journey to their location, the traveler never knows where they are going.

New England Coach Mystery Trips

New England Coach offers a variety of tours that suit your needs. They offer retail tours which are open to the public and private pre-formed tours for groups. The tours can be one-day trips or multi-day trips .

One tour, in particular, stands out against the rest. New England Coach’s mystery trips are its fastest and most popular tours according to Belinda Grace-Leonard, Vice President and co-owner of the company.

“Honestly, it’s something that would never sell on a piece of paper,” said Grace-Leonard. “It’s something that people have never heard about or have never done.”

The mystery trips give New England Coach the opportunity to give people an experience that they wouldn’t normally know about. The company wants to give people unique experiences that they may not sign up for on their own.

Keeping it a Secret

“It’s all about the surprise,” said Grace-Leonard. “We don’t tell them anything about the tour until we’re on tour.”

If you’re concerned about what to pack, don’t be. For the mystery trips, New England Coach makes sure to send you a packet of information that does not reveal too much about the tour. The packet informs you of what the temperatures are going to be and gives slight clothing suggestions.

The tour company may give some clues and hints, but only once on the road, and you are never going to know more than one stop ahead. Some people attempt to trick information out of the tour leaders, but they never give in.

What is included?

What you pay, which varies for each trip, includes a few amenities.

Your transportation is always included. Along with breakfast and oftentimes lunch and dinner. All attractions and hotels are included. Tour managers and sometimes guides are also included in the upfront cost.

What to expect on a Mystery Trip?

Everything with New England Coach revolves around group travel, so you can always expect to be with other travelers excited to discover something new. The tour managers work to get everyone involved and make sure everyone is enjoying their trip.

Grace-Leonard, who both plans and creates the itineraries for the mystery trips, tries to stay away from heights or anything that might cause motion sickness.

This means that she usually steers clear from boats. She doesn’t want to have to give anything away to travelers, so tries not to book tours that would require special warnings.

With its trips, New England Coach’s goal “is putting together a great product and seeing the enjoyment that it brings to other people’s lives,” said Grace-Leonard.

Learning en Route

When going on mystery trips with New England Coach, you are sure to learn something new from your travels, whether it’s a fact from a museum you stopped at or something you learned from a local.

In the past, the mystery trips have taken travelers to a wolf sanctuary in Eastern Massachusetts, the American Banjo Museum in Oklahoma, alpaca farms in Amish country, and so many more fun and exciting places that take you off the beaten road.

For Grace-Leonard, one of her favorite places she has ever taken a group was Custer State Park in South Dakota .

During the day, the tour group rented jeeps which they rode through the range allowing them to see the regrowing Bison population up-close.

Afterward, they retreated to a ranch in the park and got on a hay wagon along with a singing cowboy who serenaded them through the park. It was an experience you would not find anywhere else.

“The next tour is always my favorite tour,” said Grace-Leonard. “I truly never get tired of taking people to new places, even if I’ve been there multiple times.”

Christian Tours

Christian Tours is a tour company that offers trips from one day to twenty-four days. The company offers international tours, cruises, and motorcoach tours.

All of the motorcoach tours depart from North or South Carolina, where the touring company is based.

Like New England Coach, Christian Tours offers mystery trips.

Grand Reunion Mystery Tour

Christian Tours has been offering the Grand Reunion Mystery Tour since the late 80s. The trips occur in November and usually last six to eight days.

“We try to keep it different and unique and not the same as our normal catalog tours or normal offerings,” said Heather Paul the customer service and personnel director for Christian Tours.

Paul said they try to have fun with their travelers on these trips, even the coach drivers get in on the fun. They might take a wrong turn somewhere or wait till the last moment to switch lanes to make the journey more exciting for the travelers.

In advance of the trip, Christian Tours gives their customers clothing suggestions and tells them the average temperature but that is all.

What is included and what to expect

“We normally feed them really well,” said Paul. Travel is often known for feeding people, Christian Tours’ mystery trip includes two meals a day that you would not want to miss.

The tour company’s annual trip also includes attractions, luggage handling, and the services of the driver and tour director.

During the mystery trip, you can expect to be up and out by 8 a.m. and usually done for the day around 6 p.m. with dinner following shortly after. Some nights there may be evening entertainment.

Christian Tours is family-friendly and aims to make people feel safe, but the company also wants people to experience something new that they cannot get from the usual catalog.

During last year’s reunion tour, Paul recounts that they did the Grafton Skytour , which took them on a gondola ride up to the top of a small mountain. They were able to have a unique dinner on top of the mountain at Aerie’s Resort in Grafton, Illinois .

Mystery trips are a new and exciting way to travel. They offer the best of traveling and exploring without the hassle of having to plan the trip yourself.

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