5 Fall Canadian Road Trips

Dating back to when cars didn’t have seat belts and making plans with friends occurred over a landline, the road trip has been a fall staple. Everyone has the “Mom and dad crammed the kids in the back of the car for a fun road trip – it was excruciating, not to be dramatic” story. And, a select lucky few even have the “Me and my best friend road-tripped across Canada – it was wild” story. And, so many of us have a story for everything in between. So, where’s your roadie this fall? Here are the hottest destinations for your road trip and tips and tricks of what to do when you finally get there.

Prince Edward County

Many would be surprised to learn that the infamous Drake Devonshire hotel is actually only the icing on top of the cake of this beautiful location. A 2-hour drive from Toronto – two-thirds of the way to Kingston, Prince Edward County is lined by beautiful beaches dotted by rolling sand dunes. The Sandbanks are a popular camping location where you can stay almost right on the beach and spend your days on one of their three expansive beaches. If camping isn’t for you, visit one of the cute Inns or rent one of the many available AirBnbs in the town of Wellington– but, book ahead as they go quickly! In Wellington you will find the quintessential small town with art galleries, delicious restaurants and cute little shops.


Stratford, the home of Justin Bieber and only 2-hours outside of Toronto, is a great destination for a weekend of small town living. Another fantastic main street, located just off the Avon river. Besides Justin Bieber, Stratford is most well known for the Stratford Festival, a multi-month performing arts festival in the city. Visit restaurants, see shows and peruse the main street, but don’t forget Stratford’s park system, which includes the T.J. Dolan Natural Area. Here you will find great trails of varying lengths for both hiking and biking. For a charming small town, it is surprising to be able to say that there is something for everyone.


Yes, a lot of people think a 4-hour drive for a weekend road trip is daunting. But, let me assure you that this one will be worth it. It is almost like going to Croatia for the weekend and if that doesn’t convince you, then I really can’t offer much more. Tall cliffs submerging into water the colour of blue Gatorade, cute little town with plenty of places to eat and shop and not far from the Bruce Trail with beautiful walking paths along the Niagara Escarpment. The Flowerpot Island sea stacks – two tall rock formations on a nature island, are a must-visit by taking a short boat ride about 6km off of the shore of Tobermory.

Niagara on the Lake

Wine, wine, wine. If you are a wine lover, well I’m sure you have already been. Just a short one-hour drive from Toronto, Niagara on the Lake boasts over 20 of Ontario’s finest wineries. Sit out on one of the winery’s outdoor patios, enjoying a glass of Chardonnay, a charcuterie board and a view of the very vines that produced the wine in your glass. Besides visiting wineries, Niagara on the Lake has so much more to offer. Picturesque hotels, nestled amongst the town’s main streets that is lined with stores, cafes and an array of restaurants. Some of the wineries even offer rooms if you would like to stay right there. If you’re looking for some exercise to work off that wine, check out the White Water Walk to walk along a quarter mile of elevated boardwalk, built along the edge of the rushing rapids.


Often overshadowed by Collingwood and The Blue Mountains, this adorable waterside town just over 2-hours drive from Toronto is a must-visit. In town, check out the harbour front located right at the mouth of the river into Georgian Bay. Also, visit the variety of art galleries, clothing stores and delicious restaurants. You will find everything from wood fire pizza with live music to bustling bakeries. If you’re there for the weekend you can even spend one day hiking the Bruce Trail – Old Baldy is a great part of the trail with sprawling views of the surrounding apple orchards and escarpment.

Contributor: Holly Mowbray

Holly is a university student from Toronto. She loves the street style of the city and the Toronto lifestyle. She is also an avid traveler, working her way through exploring the world.


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