Windsor to Toronto fall road trip

Set out on a road trip to Toronto with stops in Windsor and Mississauga for big-name entertainment, pro-sports, epic food and nightlife.

And add in a dose of nature for a chance to witness the gorgeous show of Canadian fall foliage.

Border crossing information

Travel documentation

Travellers to Canada must present a valid passport or NEXUS card. Find out what else you need to know to fly into Canada.

Check border wait times 

Border crossing locations from Michigan into Canada include:
Detroit Windsor Tunnel from Detroit, Michigan to Windsor, Ontario
Ambassador Bridge from Detroit, Michigan to Windsor, Ontario

Windsor

From casino entertainment to unique whisky tours, you’re guaranteed good food, drinks and fun in Windsor.

Places to stay in Windsor

Caesars Windsor

Luxury casino resort with chic suites fitted with whirlpool tubs, and stellar river and city views. Resort amenities include a fitness area, pool, restaurants, bar and entertainment.
Location:  377 Riverside Drive East, Windsor

Best Western Plus Waterfront Hotel

Overlooking the Detroit River, this is another great option for accommodations in the heart of downtown Windsor.
Location: 277 Riverside Drive West, Windsor

Things to do in Windsor

Caesars Windsor Casino

Try your luck with exciting table games like Blackjack, Roulette and Poker and over 2,000 slot machines.
Location: 377 Riverside Drive East, Windsor

The Colosseum

Caesars Windsor’s state-of-the-art entertainment venue for big-ticket live music, comedy and more.
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

Where to eat and drink in Windsor

The Twisted Apron

A popular spot for French toast, waffles and omelettes in the Walkerville neighbourhood.
Location: 1833 Wyandotte Street East, Windsor

Terra Cotta Pizzeria

Discover Windsor-style pizza with shredded pepperoni, local Galati mozzarella and canned mushrooms.
Location: 318 Pelissier Street, Windsor

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

Fourteen Restaurant Sky & Lounge

Upscale dining with an elevated view overlooking the city and river. Be sure to make reservations well in advance.
Location: 100 Ouellette Avenue, Windsor

Walkerville Brewery 

For local, unique and hand-crafted small-batch craft brews.
Location: 525 Argyle Road, Windsor

Mississauga

Approximate distance and travel time from Windsor: 220 miles (350 kilometres), 3.5 hours

Savour international flavours, experience dynamic culture and emerging visual arts scene and explore nature bathed in fall colour in Mississauga, Canada’s sixth largest city.

Things to do in Mississauga

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

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

Where to eat and drink in Mississauga  

Posta Italbar Cucina

The innovative menu options are inspired from various Italian regions.
Location: 31 Lakeshore Road East, Mississauga         

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

Toronto

Approximate distance and travel time from Mississauga: 18 miles (30 kilometres), 45 minutes

Revel in Canada’s most multicultural and vibrant city. Experience top theatre, pro-sports, entertainment and accommodations in Toronto.

Places to stay in Toronto

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 available.
Location: 75 Bremner Boulevard, Toronto

Ace Hotel Toronto

Enjoy cozy rooms, craft cocktails and skyline city views at one of Travel + Leisure’s top 100 new hotels in the world.
Location: 51 Camden Street, Toronto

Fairmount Royal York

Toronto’s landmark heritage hotel is within walking distance of most downtown sports and nightlife. Valet parking at the east entrance, self-parking options nearby are also available.
Location: 100 Front Street West, Toronto

Park Hyatt Toronto

Opposite the Royal Ontario Museum and a short walk to Yorkville, one of Toronto’s trendiest neighborhoods. 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 electric car charging station provided.
Location: 325 Bay Street, Toronto

Things to do in Toronto

CN Tower

Toronto’s must iconic attraction, and take in unmatched city views from observation platforms, the revolving 360 Restaurant or along EdgeWalk, an exciting daredevil walk around the outside of the top needle of the tower.
Location: 290 Bremner Boulevard, Toronto

Royal Ontario Museum (ROM)

The largest museum in Canada showcasing art, culture and natural history from around the world.
Location: 100 Queen’s Park, Toronto

Art Gallery of Ontario (AGO)

One of the largest art collections in North America.
Location: 317 Dundas Street West, Toronto

Hockey Hall of Fame

Celebrate Canada’s national winter 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 in Toronto

Nuit Blanche

Explore over 100 contemporary art installations and exhibits displayed across the city for one full night from dusk to dawn.
Date: October 5, 2024

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) seasons begin.

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 in downtown Toronto.
Dates: November 1-10, 2024

Mirvish

Home to some of the best theatre productions to Toronto. Check what’s on stage during your visit.
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 USHER, Billie Eilish and Bruce Springsteen.
Location: 40 Bay Street, Toronto

Where to eat and drink in Toronto

Toronto restaurants and cafes

With over 9,000 restaurants and over a dozen craft breweries, you’ll never run out of great food and drink options in this city. 

MICHELIN restaurants

Toronto is the first Canadian city to be recognized in the MICHELIN Guide, with over a dozen restaurants starred.

Bib Gourmand restaurants

Seventeen restaurants across the city were recognized for superb menus at a 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, enjoy a tour and tasting at Spirit of York Distillery. 
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 foodie destination with cool brewpubs, bars and bistros.
Location: Ossington Street

Extend your trip to Ontario with more road trip itineraries.

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