Windsor to Toronto fall road trip
Combine the best of urban culture, food and fun with stunning fall colour across the border in Ontario, Canada.
Toronto
Stop 1: Windsor
Whether it’s big wins at the casino or on the golf green, Windsor serves up unbeatable eats, drinks and entertainment.
Attractions and activities
Caesars Windsor
Try your luck with exciting table games like Blackjack, Roulette, Poker and over 2,000 slot machines at Caesars Windsor Casino or catch a live show at The Colosseum. This season includes comedy greats like Tom Segura, Russell Peters and Sebastian Maniscalco.
Location: 377 Riverside Drive East, Windsor
Ambassador Golf Club
An 18-hole, 71-par championship golf course and driving range designed by the renowned Thomas McBroom.
Location: 1025 Sprucewood Avenue, Windsor
Food and drink
WindsorEats Food Hall
Home to Windsor’s largest patio, a selection of food trucks, popular margarita flights, craft beer, special events and vibrant murals in Electric Avenue Art Alley.
Location: 400 Erie Street East Unit 3, Windsor
Antonio’s Original Pizza
Sample the famous Windsor-style thin-crust, stone-baked pizza, topped with vine-ripened tomato sauce, shredded pepperoni, premium bacon, local Galati mozzarella, finely diced green peppers, and canned mushrooms. Try it before you judge!
Locations:
Mezzo Ristorante & Lounge
Voted the best restaurant as well as the most romantic dining experience in Windsor, for its food, atmosphere and entertainment.
Location: 804 Erie Street East, Windsor
Walkerville Brewery
For local, unique and hand-crafted small-batch craft brews.
Location: 525 Argyle Road, Windsor
Places to stay
Caesars Windsor
In addition to the casino, Caesars is a luxury resort featuring chic suites equipped with whirlpool tubs and offering stellar views of the river and city.
Location: 377 Riverside Drive East, Windsor
Best Western Plus Waterfront Hotel
Overlooking the Detroit River, this is another excellent option for accommodations in the heart of downtown Windsor.
Location: 277 Riverside Drive West, Windsor
Stop 2: Mississauga
Approximate distance and travel time from Windsor: 220 miles (350 kilometres), 3.5 hours.
Explore international flavours, dynamic culture, an emerging visual arts scene and nature bathed in fall colour in Mississauga, Canada’s sixth largest city.
Attractions and activities
Mi Museum
Bend the rules of reality with interactive optical illusions at this entertaining museum located next to Mississauga’s largest shopping centre, Square One.
Location: 4174 Confederation Parkway, Mississauga
Square One Shopping Centre
Square One is Ontario’s largest shopping mall, offering over 330 stores, diverse dining options and entertainment experiences.
Location: 100 City Centre Drive, Mississauga
Parks and trails
Nature and green spaces are abundant in Mississauga. Admire the fall foliage along the raised boardwalks at Rattray Marsh, and enjoy bird watching at Riverwood Conservancy, home of over 180 bird species.
BraeBen Golf Course
Play a round of 9-hole golf at Mississauga’s picturesque public golf course.
Location: 5700 Terry Fox Way, Mississauga
Food and drink
Avani
Lauded as one of the best Indian restaurants in the area with a robust cocktail and beer and wine list.
Location: 801 Matheson Boulevard West, Mississauga
Grillado
Treat yourself to mouth-watering Portuguese-style chicken marinated with a delicious South African twist.
Location: 5165 Dixie Road Unit 2B, Mississauga
El Mariachi Tacos and Churros
Relax on the outdoor patio and enjoy authentic Mexican cuisine paired with a unique cocktail.
Location: 235 Queen Street South, Mississauga
Stonehooker Brewing Company
In addition to a great menu and a variety of craft beers, enjoy live music and comedy on select days.
Location: 866 Lakeshore Road East, Mississauga
Stop 3: Toronto
Approximate distance and travel time from Mississauga: 18 miles (30 kilometres), 45 minutes.
Experience top-notch theatre, professional sports, entertainment and accommodations in Toronto, Canada’s most multicultural and vibrant city.
Attractions and activities
CN Tower
Visit Toronto’s most iconic attraction for unmatched city views from observation platforms, the revolving 360 Restaurant, or along EdgeWalk, an exciting daredevil walk around the outside of the top needle.
Location: 290 Bremner Boulevard, Toronto
Royal Ontario Museum (ROM)
The largest museum in Canada showcases art, culture and natural history from around the world. From Flemish masterworks to Chinese Zodiac to a deep dive on sharks, the exhibits are as intriguing as they are diverse.
Location: 100 Queen’s Park, Toronto
Hockey Hall of Fame
Celebrate Canada’s national sport and pay tribute to its greatest players.
Location: 30 Yonge Street, Toronto
Toronto Shopping Guide
From high fashion to vintage markets, there’s a shopping experience for just about every whim and fancy.
Toronto’s nightlife
For what to do after dark, check out the city’s best nightclubs and sports bars.
Events and entertainment
Pro-sports games
Catch a Major League Baseball (MLB) or Canadian Football League (CFL) game before the season wraps up at the end of September. In October, professional basketball (NBA) and hockey (NHL or PWHL) seasons begin.
Nuit Blanche
Explore contemporary art installations and exhibits displayed throughout the city for one night, from dusk to dawn. This year’s theme, “translating the city,” explores how urban centres can be reimagined and communicated through art.
Date: October 4, 2025
The Royal Agricultural Winter Fair
The country comes to the city for almost two weeks every year, delivering the best in agricultural achievements, local food, crafts, entertainment and equestrian shows at Exhibition Place.
Dates: November 7–16, 2025
Mirvish
Catch some of the best theatre productions in North America. One of the stage shows this fall is MJ, the musical, a multiple Tony Award-winning production centred around the making of Michael Jackson’s 1992 Dangerous World Tour.
Locations:
Ed Mirvish Theatre, 244 Victoria Street, Toronto
Princess of Wales Theatre, 300 King Street West, Toronto
Scotiabank Arena
Get tickets well in advance for big-name shows like Lady Gaga, Dua Lipa, Lorde and Adam Sandler.
Location: 40 Bay Street, Toronto
Food and drink
Toronto restaurants and cafes
With close to 10,000 restaurants and numerous craft breweries, you’ll never run out of great food and drink options in this city.
MICHELIN restaurants
Toronto was the first Canadian city to be recognized in the MICHELIN Guide, with over a dozen restaurants awarded stars and more establishments earning a Bib Gourmand status for great value.
The Distillery District
A pedestrian-only neighbourhood with Victorian industrial architecture, cobblestone streets and a cluster of bars, cafés, restaurants, bakeries, brewpubs and a chocolate-maker. Naturally, there’s also a distillery in the district.
Location: Distillery District, Toronto
Bloor and Yorkville
Once a bohemian hub, this neighbourhood is now known for its high-end retail shopping and some of Toronto’s finest restaurants, such as Sassafraz, Buca Osteria & Bar, Café Boulud and Alobar.
Location: Yorkville, Toronto
Ossington Strip
This west side street has flourished into a hip culinary destination with cool brewpubs, bars and bistros.
Location: Ossington Street, Toronto
Places to stay
Le Germain Hotel Maple Leaf Square
Steps away from the Scotiabank Arena and the Rogers Centre, which is convenient if you are seeing a show or catching a game. Indoor valet parking is available.
Location: 75 Bremner Boulevard, Toronto
Park Hyatt Toronto
Opposite the Royal Ontario Museum and a short walk to Yorkville, one of Toronto’s trendiest neighbourhoods. The cityscape view from the rooftop lounge is outstanding. Valet parking offered.
Location: 4 Avenue Road, Toronto
St. Regis Toronto
A five-star property with all the luxury services and amenities you’d expect and then some, like the white-glove butler service and the daily Champagne sabering ritual. Valet parking and an electric car charging station are provided.
Location: 325 Bay Street, Toronto
Getting here and around
Customs documentation
Travellers to Canada must present a valid passport or NEXUS card. Get more information on customs, passports and requirements.
Crossing the border
There are 14 road border crossings from the United States into Ontario. Before travelling, check border wait times.
The closest border crossing locations from Michigan into Canada include:
- Detroit Windsor Tunnel, Detroit, Michigan to Windsor, Ontario
- Ambassador Bridge, Detroit, Michigan to Windsor, Ontario
- Blue Water Bridge, Port Huron, Michigan to Point Edward and Sarnia, Ontario
Getting around
This itinerary is designed as a self-driving road trip in a private vehicle or motorcycle. However, there are alternative ways to get around in Toronto.
Toronto has an extensive transit system, including a city streetcar, subway and bus network, as well as a regional train service with connections to Mississauga and Hamilton. Buy a TTC Day Pass to move around the city at your leisure.
Bike Share Toronto provides bicycle rental kiosks across downtown Toronto.
Know before you go
Check out Tourism Windsor Essex, Visit Mississauga and Destination Toronto for more local insights and trip planning information.
Weather
Ontario is a four-season destination. Temperatures and weather change dramatically throughout the year. Learn more about the weather in Ontario and get suggestions on what to pack and how to prepare for a fall road trip.
Currency, measurements and holidays
Find helpful things to know about Ontario, including Canadian currency, measurements and public holidays acknowledged in the province.
Safety information
Emergencies aren’t always the first thing we consider when planning a vacation, but it’s essential to know who to contact in an emergency.
Land acknowledgement
Windsor is situated on the traditional territory of the Three Fires Confederacy of First Nations, which includes the Ojibwe, Odawa and Potawatomi. The Robinson-Huron and Upper Canada Treaties cover the land.
Toronto is on the traditional territory of various Indigenous nations, including the Mississaugas of the Credit, the Anishnabeg, the Chippewa, the Haudenosaunee and the Wendat peoples. Toronto is covered by Treaty 13 with the Mississaugas of the Credit.
Last updated: August 6, 2025