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.

    An audience enjoys a live music show.

    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:

    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 before travelling. Border crossing locations from Michigan into Canada include:


    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

    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

    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

    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.

    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


    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 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

    Scotiabank Arena : Get tickets well in advance for shows like Shania Twain, Queen & Adam Lambert, Drake, SZA, Wu-Tang Clan and Aerosmith.
    Location: 40 Bay Street, 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.

    If you are looking for more trip planning support, connect with one of our travel counsellors who can help you build your road trip itinerary.

    Last updated: February 22, 2024

    Looking for Ontario travel advice?

    Our experts are here to help you plan your perfect trip. Call or book today.