Canada’s two largest cities, Toronto and Montreal, both offer warm Canadian hospitality and big-city attractions that range from contemporary art galleries to international cuisine to massive music festivals. And while a straight drive between the two takes approximately six hours, there’s no need to rush the route.
Because while the two big cities offer plenty of attractions, there are plenty of unexpected stops along the way. This is a multiday itinerary, so plan for a couple of overnights along the way, such as in Prince Edward County or Ottawa.
Now, let’s get the car — and this vacation — started.
As always, check for travel restrictions and closures before planning your trip.
Start: Toronto
Hugging the shoreline of Lake Ontario, Toronto offers stellar opportunities to explore its waterfront. Start with the Great Lakes Waterfront Trail, a massive route that traces the Great Lakes coastlines and passes directly through Toronto.
Grab snacks and plan for an “out and back” route to Humber Bay Park East (6.5 miles/10 kilometers from the CN Tower) where 47 acres of park space offer wooden boardwalks, pebbled beaches and the perfect vantage point for a Toronto skyline photograph. (FYI: The Westin Harbour Castle, Toronto is currently offering complimentary Zygg e-bike rentals.)
Next, do as the locals do and head to Toronto Islands. Accessed via the Jack Layton Ferry Terminal, the islands offer opportunities for swimming, cycling, paddling, dining and family fun. A great way to tackle the islands is to take a ferry to Hanlan’s Point and walk (or bike) counterclockwise toward Ward’s Island.
Summer months offer outdoor adventure at Ward’s Island Beach or Centreville Amusement Park. To up the ante, rent a stand-up paddleboard or a kayak from Toronto Island SUP. And for those looking to shed all constraints, the clothing optional Hanlan’s Point Beach provides a setting to really let it all hang out.
Back in the city, nab a taste of the tropics at Little Jamaica in the York district. Black-owned Sunlight Bakery offers up fresh-baked bread and decadent treats. The beef patties at TinNel’s are mouthwatering and affordable, while neighboring Enchilados Taqueria aces the taco eating experience: fresh and bountiful.
When the sun sets, head to the pedestrian-only Distillery District, a refurbished neighborhood known for its boutiques, art galleries and modern eateries housed in former industrial buildings. The former whiskey distillery is a visual playground for the Instagram crowd. In December, the annual Toronto Christmas Market transforms the cobblestone lanes into a snow-globe twinkle fest.
Stop: Prince Edward County
Over the past decade, Prince Edward County has become one of Ontario’s most beloved destinations, and with good reason. The winemaking region boasts some of the nation’s best wines, along with landscapes that are uncommon in Canada.
Formed by glaciers 12,500 years ago, the local sandbanks are the world’s largest bay-mouth dune barrier formation. Art lovers will want to pop into ANDARA, where the barn-turned-gallery showcases art inspired by the county itself.
Stop: Ottawa
Welcome to Canada’s Capital. Ottawa doesn’t have the bustle of bigger Canadian cities, but that’s part of its appeal. First-time visitors will want to pop into the ByWard Market to sample Canadian cheeses and BeaverTails (a much-loved Canadian pastry).
Ottawa is also home to several national museums and galleries. The Canadian Museum of History — located on the banks of the Ottawa River directly opposite Parliament Hill — offers a framework to understand Canada’s somewhat tumultuous past and its contemporary culture.
The National Gallery of Canada is home to one of the finest collections of Indigenous and Canadian art in the world and warrants several hours of wandering.
When you’re ready to kick back for a beverage, head to Tooth and Nail Brewing Company where the Rhapsody Sour (notes of peach and green tea) makes a sweet conclusion to the day.
Finish: Montreal
Canada’s cultural capital never ceases to evoke wonderment. A first visit to the city is not complete without meandering through the handsome cobblestone streets of Old Montreal.
With newer buildings juxtaposed with architecture dating back as far as 1685, visitors can see how the city began and how it has morphed over the centuries. Jump from the past to the present with a visit to Centre Phi, a multifunctional contemporary art center that offers a revolving program ranging from VR experiences to artist talks to master classes.
Montreal loves to eat. While the iconic foods such as poutine, bagels and smoked meat are certainly worth savoring, don’t just stop there. A visit to one of the local farmers markets provides the opportunity to sample regional produce and goodies, such as apple varieties, maple syrup treats and a gamut of locally produced meats.
When you’re ready for dessert, stroll to Fous Desserts (“fous” means “crazy”) for crazy-good Viennoiseries, pies and cakes.
To wrap up the itinerary, wander through Montreal’s Jardin Botanique. No matter the season, the 185-acre botanical gardens offer a remarkable diversity of plants in some 20 themed gardens and 10 exhibition greenhouses, making for a calming finish to a superb road trip.
Our podcast, About the Journey, features an episode specifically about a Toronto to Montreal road trip. Don’t miss it!
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