Windsor to Toronto: Exciting sports, events and entertainment
Experience a warm welcome with world-class entertainment, pro-sports action, top attractions, great shopping and lively events just across the border in Ontario, Canada.
Toronto Harbourfront
Stop 1: Windsor
From casino entertainment to championship golf, you’re guaranteed good food, drinks and fun in Windsor, Ontario.
Things to do
Caesars Windsor Casino
Try your luck at table games like Blackjack, Roulette and Poker or on the over 1,700 slot machines and see what’s on at The Colosseum, a 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 golf course architect Thomas McBroom.
Location: 1025 Sprucewood Avenue, Windsor
Urban Surf Co.
Get out on the water with kayak or stand up paddle rentals from Urban Surf Co.
Location: 55 East Pike Creek Road, Windsor
Where to eat and drink
Best places to eat in Windsor
Here’s a round-up of some of the most exciting spots to eat in Windsor, including where to sample authentic Windsor-style pizza with shredded pepperoni, local Galati mozzarella and canned mushrooms.
The Twisted Apron
Enjoy delicious French toast, waffles and omelettes in the Walkerville neighborhood.
Location: 1968 Wyandotte Street East, Windsor
Mezzo Ristorante & Lounge
This spot is often voted the most romantic dining in Windsor for its food, atmosphere and entertainment.
Location: 804 Erie Street East, Windsor
Great breweries
For local, small-batch craft brews, choose from:
- Walkerville Brewery at 525 Argyle Road, Windsor
- Frank Brewing Company at 12000 Tecumseh Road East, Windsor
- Chapter Two Brewing at 2345 Edna Street, Windsor
Places to stay
Caesars Windsor
Windsor’s luxury casino resort provides chic suites with whirlpool tubs and stellar river or city views. Other amenities include a spa, fitness area, pool, restaurants, bar and entertainment.
Location: 377 Riverside Drive East, Windsor
Holiday Inn Express Windsor Waterfront
Another great option for accommodations in the heart of downtown Windsor, overlooking the Detroit River.
Location: 33 Riverside Drive East, Windsor
Stop 2: Hamilton
Approximate travel from Windsor to Hamilton: 185 miles (300 kilometres), 3 hours
Hamilton, the ‘City of 100 Waterfalls’, also boasts art, culture and cuisine and many of the iconic Heated Rivalry filming locations.
Things to do
FirstOntario Centre
Elite sporting events and big-ticket artists are billed to perform at Hamilton’s largest live music and entertainment venue.
Location: 101 York Boulevard, Hamilton
Hamilton Tiger-Cats
The Canadian Football League season runs into October, with Hamilton’s pro team playing at the Tim Hortons Field stadium.
Location: 64 Melrose Avenue North, Hamilton
Museums and heritage sites
Tour interesting historical museums and sites, including the carefully restored Dundurn Castle built in the 1830s, HMSC Haida, a Royal Canadian Navy destroyer that served in several wars and the Canadian Warplane Heritage Museum.
Locations:
- Dundurn Castle, 610 York Boulevard, Hamilton
- HMSC Haida, Pier 9, 658 Catharine Street North, Hamilton
- Canadian Warplane Museum, 9280 Airport Road, Mount Hope
Where to eat and drink
The Electric Diner
For a leisurely brunch, head to the Electric Diner in Hess Village or Lister Block.
Locations:
- Hess Village, 96 George Street, Hamilton
- Lister Block, 28 James Street North, Hamilton
The French Bistro
Great food, impeccable service and warm ambiance, from weekend brunch to late-night dessert.
Location: 37 King William Street, Hamilton
Berkeley North
The seasonal, West Coast-inspired small plate menu is perfect for sharing.
Location: 31 King William Street, Hamilton
Born & Raised
Chef Vittorio’s Italian roots and love of local shine with a late-night menu for night owls.
Location: 224 James Street North, Hamilton
Quatrefoil Restaurant
Refined, contemporary cuisine paired with a beautiful wine menu from Wednesdays to Saturdays.
Location: 16 Sydenham Street, Dundas
Collective Arts Brewing
One of Hamilton’s flagship brewhouses serves craft beer, cider and sparkling hard tea, along with a full calendar of arts and cultural events.
Location: 207 Burlington Street East, Hamilton
Where to stay
C Hotel by Carmen’s
European-inspired boutique experience with themed room décor and an on-site Italian restaurant.
Location: 1530 Stone Church Road East, Hamilton
The Pearle Hotel & Spa
An elegant waterfront property with a luxurious spa, earth-to-table farm cuisine at the onsite Isabelle Restaurant & Lounge and endless, serene lake views.
Location: 3 Elizabeth Street, Burlington
Stop 3: Toronto
Approximate travel from Hamilton to Toronto: 42 miles (68 kilometres), 56 minutes
Revel in Canada’s most multicultural and vibrant city. Experience top theatre, pro-sports, entertainment, events and accommodations in Toronto.
Things to do
CN Tower
Visit Toronto’s most iconic attraction and take in unmatched city views from observation platforms. Dine at the revolving 360 Restaurant or brave the EdgeWalk, an exciting daredevil walk located outside around the top of the tower, 116 storeys above ground.
Location: 290 Bremner Boulevard, Toronto
Royal Ontario Museum (ROM)
Showcasing art, culture and natural history from around the world, the ROM is the largest museum in Canada.
Location: 100 Queen’s Park, Toronto
Art Gallery of Ontario (AGO)
View one of the largest art collections in North America, including permanent and featured exhibits.
Location: 317 Dundas Street West, Toronto
Museum of Contemporary Art (MOCA)
Cultural, social and other thought-provoking issues are explored at Toronto’s contemporary art gallery.
Location: 158 Sterling Road, #100, Toronto
Arcadia Earth
Art and technology become one in this immersive experience, focusing on the environment, sustainability and climate change. Large-scale artistic installations paired with augmented and virtual reality aim to inspire visitors to help create a better world.
Location: 486 Front Street West, Toronto
Mirvish
Check what’s on stage during your visit. From The Book of Mormon to Chicago, Mirvish brings some of the best theatre productions to Toronto.
Locations:
- Royal Alexandra Theatre, 260 King Street West, Toronto
- Princess of Wales Theatre, 300 King Street West, Toronto
Scotiabank Arena
Get tickets well in advance for top crowd pleasers like Demi Lovato, A$AP Rocky, Lionel Richie and Olivia Dean.
Location: 40 Bay Street, Toronto
RBC Ampitheatre
Kid Cudi, Paul Simon, Santana and the Doobie Brothers and Pitbull are just a few of the acts performing this summer.
Location: 909 Lake Shore Boulevard West, Toronto
Toronto Symphony Orchestra
Enjoy a diverse range of symphonies this summer, from Mendelssohn and Beethoven to the ELDEN RING Symphonic Adventure.
Location: 60 Simcoe Street, Toronto
National Ballet of Canada
Don’t miss Kismet / Emma Bovary at the Four Seasons Centre for the Performing Arts.
Location: 145 Queen Street West, Toronto
FIFA World Cup 2026™
Pro sports fans will not be disappointed in Toronto. The Toronto Stadium (BMO Field) will be the first Canadian venue to host a FIFA World Cup 2026™ men’s match on select dates from June 12 to July 2, 2026. Football enthusiasts can also catch a Toronto FC soccer match at BMO Field.
Toronto Blue Jays
Baseball season will be in full swing, so catch a Blue Jays game at the Rogers Centre.
Location: One Blue Jays Way, Toronto
Toronto Argonauts
The Canadian Football League season runs until October. Home games at held at the BMO Field.
Location: 170 Princes’ Boulevard, Toronto
Hockey Hall of Fame
Visit the Hockey Hall of Fame, a celebration of Canada’s national winter sport and a tribute to its greatest players.
Location: 30 Yonge Street, Toronto
Comedy clubs
Catch a comedy show with local comedians and rising comic stars at Comedy Bar, YukYuks Comedy Club or Second City, the club that launched the careers of countless comedy treasures, including Bill Murray, John Candy, Eugene Levy and Catherine O’Hara.
Locations:
- Comedy Bar, 945 Bloor Street West, Toronto and 2800 Danforth Avenue, Toronto
- YukYuks, 224 Richmond Street West, Toronto
- Second City, One York Street, 110 Harbour Street, Toronto
Shopping in Toronto
From high fashion to vintage markets, there’s a shopping experience for just about every whim and fancy. Chart your shopping course with the Toronto Shopping Guide.
Toronto’s nightlife
Check out Destination Toronto for what to do after dark.
Festivals and celebrations
North by Northeast (NXNE)
Canada’s answer to NXNW showcases the best new and emerging talent (June 10–14, 2026).
Pride Toronto
Toronto is transformed during the largest Pride event in Canada, celebrating the 2SLGBTQI+ community for a full month, culminating in a festive parade (June 25–28, 2065).
Toronto Fringe Festival
Alternative, unconventional and entertaining theatre (June 30–July 12, 2026).
Toronto Caribbean Carnival
An epic event showcasing the best of Caribbean culture, music and food (July 30–August 3, 2026).
Where to eat and drink
Food-forward neighbourhoods
As one of the world’s most multicultural cities, Toronto is also one of the best places on the planet for people who love good food and drink. With thousands of restaurants and over a dozen craft breweries, you’ll never run out of great food and drink options in this city.
Follow your appetite to flavours from around the world in Toronto’s Greektown, Chinatown, Little India or Little Italy. There are also pockets of the city that have flourished into culinary destinations, such as the Distillery District, the Ossington Strip and the Yorkville neighbourhood.
MICHELIN-starred restaurants
Make it an extra memorable date and book reservations at one of Toronto’s recently awarded restaurants.
Culinary Adventure Co. or Tasty Tours Toronto
Get the inside scoop from local experts at on a themed culinary tour.
Places to stay
Le Germain Hotel Maple Leaf Square
Just steps away from the Scotiabank Arena and the Rogers Centre, this stylish downtown hotel is convenient if you are seeing a show or catching a game. Indoor valet parking is 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
Park Hyatt Toronto
The Park Hyatt is located opposite the Royal Ontario Museum, a short walk to Yorkville, one of Toronto’s trendiest neighbourhoods. The cityscape view from the rooftop lounge is outstanding. Valet parking is offered.
Location: 4 Avenue Road, Toronto
St. Regis Toronto
This five-star property offers 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
Crossing the border
Required documents
U.S. visitors to Canada must present a valid passport or NEXUS card.
Find out what else you’ll need to know to cross the border into Canada.
Border crossing locations
There are several road border crossings from the United States into Ontario. 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
- Gordie Howe International Bridge, Detroit, Michigan to Windsor, Ontario (set to open in 2026)
- Blue Water Bridge, Port Huron, Michigan to Point Edward and Sarnia, Ontario
Before travelling, check border wait times.
Know before you go
Check out Tourism Windsor Essex, Tourism Hamilton and Destination Toronto for more local insights and trip planning information.
Contact an Ontario travel planner for help in creating a customized itinerary that meets your needs.
Getting around and accessibility
You’ll need a private vehicle to complete this self-driving Ontario road trip in its entirety.
Toronto has an extensive transit system, including city streetcars, subway and bus network and a regional train service with connections to Mississauga and Hamilton. Buy a TTC Day Pass to move around the city at your leisure.
Download the Access Now app to search for accessible businesses, trails and outdoor experiences in Ontario.
Weather
Summers in Ontario are warm and pleasant, with the possibility of hot and humid conditions. Spring and fall conditions are more variable, with the chance of frost and more precipitation before mid-May and after mid-September.
Learn more about the weather in Ontario and get suggestions on what to pack and how to prepare for your trip.
Currency, measurements and holidays
Find useful 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 knowing who to contact in an emergency is important.
Last updated: April 17, 2026