10 of the Best Road Trips to Take for Labour Day Weekend

Get out of the city before the summer officially ends! This Labour Day weekend, skip the typical road trip to Montreal and try one of these instead.
10 of the Best Road Trips to Take for Labour Day Weekend

Labour Day is one of those holidays that’s a little bittersweet. While a day off from work is always appreciated, it also marks the unofficial end of summer. You know once Labour Day comes around that it won’t be long before we will have to trade in our tees and tank tops for toques and jackets.

Which is why we highly recommend making the most of it with an end-of-summer road trip. It’s easy to get trapped in the bubble that is the GTA and forget that there are so many cool towns and cities to explore in Ontario.

Whether you’re a nature lover or a hardcore foodie, here are a few places you need to add to your end of summer road trip bucket list.

Port Dover

Located about two hours south of Toronto, Port Dover looks and feels more like an exclusive tropical resort than a small town Ontario. The popular Port Dover Beach even boasts real palm trees! If you’re not much of a beach bum, you can check out the picturesque pier and lighthouse, or venture into the downtown core where you’ll find a variety of boutiques, restaurants, and cute cafes.

Elora Gorge

For all you nature buffs, Elora Gorge is a great choice for a quick getaway. The gorge itself is beautiful (or should we say, gorge-ous?), boasting over 70 foot tall limestone cliffs and breathtaking views. For $40, you can rent a tube, helmet and life jacket to float down lazy river and see the cliffs up close and personal. Or if you’re up to the challenge, The Elora Cataract Trail takes you down the gorge and right to the river’s edge. Oh, and don’t forget to stop by the Quarry for cliff jumping and lazing on the sand.

elora gorge
Tubing the Elora Gorge (Image: Instagram/@labriesv)


If you think Kingston, Ontario is just a university town, you are sorely mistaken. The historic city has plenty of cool activities for weekend road trippers. For example, you can go on a guided tour of Fort Henry and be transported to 19th century military life, or you can partake in a scenic 1000 Islands cruise. Music lovers should head to Confederation Park to check out Music in the Park, Kingston’s outdoors summer concert series that features the sweet sounds of the town’s local musicians.

Prince Edward County

If you’re a foodie, a trip to Prince Edward County is a must-do! Named ‘the gastronomic Capital of Ontario,’ this area is known far and wide for its wineries, breweries and top-notch restos. It also doesn’t hurt that this place is too adorable for words – we highly suggest checking into one of the region’s charming B&Bs and soaking in all the small-town charm P.E.C. has to offer. And if it’s a beach you’re after, Sandbanks National Park is right there! 

Take a wine tour by bike with County Wine Tours in P.E.C (Image: Instagram/@digidharma)


Canada’s Capital is a great choice if you want a road trip destination that has a little bit of everything. Parliament Hill and the nearby Byward Market are a great place to start. When you get tired of the city, venture to Gatineau Park for a bit of nature, that’s conveniently only 15 minutes from downtown Ottawa.


For theatre aficionados, a trip to Niagara-on-the-Lake should definitely be on your summer ‘17 bucket list. The town’s Shaw Festival is currently on until October, meaning Labour Day weekend is an excellent opportunity to check it out. The theatre even has a backstage tour for those who want to learn more about the history of the theatre.

Niagara on the Lake (Image: Instagram/@theshamwow)


The city may not scream “summer tourist destination,” but that’s exactly what makes it such a great place to check out. The town’s Riverside Park is a lovely place to unwind, thanks to its many walking paths and shady trees that were just made for napping under. Plus, on the way there you can make a pitstop at the Terre Bleu Lavender Farm and grab an insta-worthy snap of the beautiful purple fields (and a scoop of their delicious ice cream).


Don’t let Hamilton’s reputation as a manufacturing hub turn you off – this city, which is also only an hour away away from Toronto, has some beautiful natural sights. For one, it’s the waterfall capital of the world – Spencer Gorge, Webster Falls, Albion Falls and Tew’s Falls all call the area home. If you’re feeling brave, head up to Dundas Peak, a popular spot for amateur photographers looking to capture the perfect shot of the area’s steep cliffs.

Tew’s Falls (Image: Instagram/@mimi_lam)


Why Windsor? This border city is bursting with history. For example, Windsor’s many walking tours will take you back in time to the Prohibition Era when the city was a major smuggling point. Windsor was also a prime destination on the Underground Railroad and as a result, the city is home to several black history museums and heritage sites.


Collingwood’s a classic road trip locale, but it’s still worthy of a mention thanks to it’s prime location. Stocked with breweries, Collingwood is the perfect spot for the beer aficionado. It’s also smack dab in the middle of cottage country, close to Blue Mountain, Wasaga Beach, and more popular tourist destinations. And speaking of cottages, renting one is one of the best ways to enjoy Collingwood. After all, nothing screams Labour Day weekend more than a lazy day spent chilling by the water with your friends and family.

What other places are worth a road trip? Let us know in the comment section.

Featured Image: Port Dover via Instagram/@laurie31490

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