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.

    Guests enjoy evening al fresco dining on an outdoor patio under twinkling lights.

    Amsterdam Brewhouse | Destination Toronto

    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


    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


    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         


    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


    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 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


    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 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.

    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: July 12, 2024

    Looking for Ontario travel advice?

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