Windsor to Toronto fall road trip: Epic entertainment, sports and nightlife
Experience the best of urban adventure and stunning autumn colour across the border in Ontario, Canada.
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 admire the gorgeous show of Canadian fall foliage.
And the best part? Your dollar goes a lot further in Ontario, Canada!
Border crossing information:
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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
Things to do in Windsor
J.P. Wiser’s Experience Tour: Visit the historic Hiram Walker & Sons Distillery, now home to J.P. Wiser’s Canadian Whisky, among other renowned labels and explore the storied history of Canadian whisky along with a tasting session.
Location: 2072 Riverside Drive East, Windsor
Where to eat and drink in Windsor
For local, small-batch craft brews, choose from:
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.
Where to eat and drink in Mississauga
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
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
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 7:00 p.m. to 7:00 a.m.
Date: September 23, 2023
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.
Just For Laughs Toronto: Some of today’s funniest comedians take to the stage during this famous festival of comedy.
Dates: September 21-24, 2023
Locations: Various venues across the city
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.
Dates: November 3-12, 2023
Location: Exhibition Place, Toronto
Mirvish: Home to some of the best theatre productions to Toronto. Check what’s on stage during your visit.
Ed Mirvish Theatre, 244 Victoria Street, Toronto
Princess of Wales Theatre, 300 King Street West, Toronto
Where to eat and drink in Toronto
Toronto restaurants, cafes and eateries don’t disappoint: With over 7,500 restaurants and over a dozen craft breweries, you’ll never run out of great food and drink options in this city.
MICHELIN starred restaurants: Toronto is the first Canadian city to be recognized in the MICHELIN Guide with over a dozen restaurants starred.
MICHELIN 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: Parliament Street to Cherry Street, south of Front Street East, 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: East of Avenue Road and north of Bloor Street East, 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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Last updated: September 14, 2023