The Top 5 Long Weekend Road Trips for Thanksgiving

With everyone heading to Thanksgiving family gatherings for the long weekend, this is the perfect time to swim against the current and take a last-minute trip to one of the great, under-the-radar cities just a drive away from Toronto.
The Top 5 Long Weekend Road Trips for Thanksgiving

With everyone heading to Thanksgiving family gatherings for the long weekend, this is the perfect time to swim against the current and take a last-minute trip to one of the great, under-the-radar cities just a drive away from Toronto. There are plenty of free and low-cost events to take advantage of, plus it’s about time you checked out these nearby underrated gems., the global leader in connecting travellers with the widest choice of incredible places to stay, has put together a list of the top cities you can hit in a few hours or less for an affordable and unconventional long weekend adventure.


Who doesn’t love a comeback story? Detroit has overcome rough times and is a thriving city that comes alive during the Fall. The Detroit Princess Riverboat hosts the Motown Dinner Cruise at $40-75 a head, complete with cocktails, dinner, live entertainment and dancing, all while taking in the sunset over the Detroit and Windsor skyline. This is a fun night out not to miss when visiting the birthplace of Motown music. A more budget-friendly activity in Detroit is exploring the diverse architecture and eccentric street art on a self-guided walking tour.

Where to Stay:
Historic Corktown has become a hipster neighborhood full of street art, coffee shops and craft beer, making it the ideal place to base yourself. Boutique hotel Trumbull & Porter, decked out with furniture from the iconic Herman Miller and vintage-style bicycles, sits right in the heart of Corktown, near restaurants and entertainment, as well as Comerica Park, Greektown and more. Be sure to check out Sugar House for its extensive cocktail menu and for the morning after, Astro Coffee will have you covered with a local favorite breakfast sandwich and strong, delicious coffee.  



Canada’s capitol has been pulling out all the stops for #Canada150 and there’s still time to take in the celebrations. As part of the ‘Ottawa Welcomes the World’ series, “Beijing Week” runs October 5th to 9th. Access to most events are free, with performances, folk music, and traditional Chinese operas, Chinese tea art, local delicacies, traditional craftsmanship including cloisonné, paper-cutting, and Beijing embroidery.

If you want to spend some time in the great outdoors then drive just 30 minutes outside of Ottawa to the quaint town of Wakefield in the Gatineau Hills of Quebec. Wander through the town to the landmark red bridge or grab a floatie and let the river take you on a natural (and free) lazy river ride!

Where to stay
The Byward Market is one of the most picturesque areas to wander around in Ottawa. Save some money on dining out and enjoy the fresh produce by picking up local goods at the market and enjoying it as a picnic on nearby Parliament Hill. Top recommended hotels in the area include the Andaz Ottawa Byward Market and The Westin Ottawa.



The Hammer is one of Canada’s largest cities and one not to be overlooked. Start off your long weekend with Free Fridays at the Art Gallery of Hamilton which offers free admission on the first Friday of each month from 4-8 pm with guided tours at 6 pm. Then explore the stunning waterfalls that surround the city, which are of course free and likely less crowded than nearby Niagara Falls.

Thanksgiving weekend will see downtown Hamilton’s first Annual Oktoberfest with the Black Forest Inn will playing host to celebrate their 50th anniversary. Free of charge to attend, locals and visitors alike are invited to eat, drink and be merry! The celebrations will take place on Ferguson Street next to the Inn between King St. East and Theatre Aquarius on King William. Prost!

Where to stay:
Hamilton has a vibrant nightlife and if you want to stay in the centre of the action then the Staybridges Suites Hamilton is your best bet as it boasts the top-rated location in the city. 64% of Canadians say that the first 24 hours of a trip are all about relaxing and resetting, making any one of Hamilton’s many cozy B&B’s perfect for some ultra chill Canadian hospitality.



Buffalo has long been a destination for Canadian shoppers looking for a bargain and now with the U.S. dollar value decreasing, it’s an even better time to get the most value for your money and pick up something for your fall wardrobe.  A must-visit for shopping in the city is Elmwood Village, the local favorite neighborhood for quirky cafés, independent retailers and trendy bars and restaurants. Allentown is the city’s artistic area worth visiting to check out the wall-size murals that cover the walls.

Film and entertainment fans will want to check out the Buffalo International Film Festival, one of the oldest and most popular film festivals in Western New York. The festival runs October 6th to 9th and offers an all-access pass (the aptly named Bison Pass) that will run you $36.97 USD and provides admission to any public screening, as well as numerous panels and parties.

Where to stay:
The Hotel Henry Urban Resort is a 15-minute walk away from Elmwood Village and housed in a stunning historic landmark, Buffalo was recently named America’s Favorite City for Architecture and it’s safe to say that this building helped contribute to the reputation!



Way more than just a University town, Kingston is a charming city with lots to offer. There’s no denying the city’s historical significance as one of Ontario’s oldest cities, wandering around the limestone buildings and watching dramatic war reenactments at Fort Henry make for a fully immersive experience.

What you may not know is that Kingston is home to the most restaurants per capita of almost any other city in Canada. Thanks to the student population, there are plenty of quality cheap eats to choose from. Try The Toucan for it’s all day breakfast or Saigon Delights if you’re craving spring rolls.

On Kingston’s doorstep is the 1000 Islands region along the border of New York State and Ontario. Cruise around the islands where you can find classic lighthouses and even a fairy tale castle on a historical boat tour, or step up your excursion with a dinner or wine tasting cruise at sunset.    

The best way to get the most out of your money is to pick up a KPass, the all-inclusive Kingston Attractions Pass. Choose from 24h, 48h or 72h tickets that get you access to museums, galleries, tours, 1000 islands cruise and more.

Where to stay:
Wake up with a view of the waterfront at the Delta Hotel by Marriott Kingston that’s in walking distance of Fort Henry and where the 1000 islands cruises take off from, not to mention it has an rooftop indoor pool for guests to enjoy.

Where will you road trip to this Thanksgiving weekend? Share your ideas in the comment section.

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