Windsor to Toronto: Exciting sports, events and entertainment

Stop 1: Windsor

From casino entertainment to championship golf, you’re guaranteed good food, drinks and fun in Windsor.

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

The Twisted Apron

Enjoy delicious French toast, waffles and omelettes in the Walkerville neighbourhood.

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

Terra Cotta Pizzeria

Discover Windsor’s passion for pizza, including Windsor-style pizza with shredded pepperoni, local Galati mozzarella and canned mushrooms.

Location: 318 Pelissier Street, Windsor

Great breweries

For local, small-batch craft brews, choose from:

• Walkerville Brewery at 525 Argyle Road, Windsor
• Craft Heads Brewing Company at 89 University Avenue West, Windsor
• Frank Brewing Company at 12000 Tecumseh Road East, Windsor
• Chapter Two Brewing at 2345 Edna Street, Windsor
• Sandwich Brewing Company at 3232 Sandwich 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 distance and travel time from Windsor to Hamilton: 185 miles (300 kilometres), 3 hours

Hamilton, the ‘City of 100 Waterfalls’ also boasts art, culture and cuisine.

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 including $2 oysters at 10:30 p.m.

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 onsite 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: Mississauga

Approximate distance and travel time from Hamilton to Mississauga: 30 miles (50 kilometres), 40 minutes

Detour to discover multicultural cuisine, waterfront trails and top shopping in the city of Mississauga, just west of Toronto.

Things to do

Square One Shopping Centre

Square One is Canada’s second-largest shopping mall with over 300 big-box stores and merchants, plus exciting games and attractions.

Location: 100 City Centre Drive, Mississauga

Mississauga Celebration Square

This popular outdoor space is a hub for events and festivals throughout the summer, such as the Latin Festival celebrating Latin American music, food and dance (July 18–20), Mosaic Festival showcasing South Asian arts and culture (August 2–3) and Italfest, a tribute to Italian heritage with traditional music, food and games (August 22–23).

Location: 300 City Centre Drive, Mississauga

Where to eat and drink

The Food District

Similar to traditional urban food markets, explore over 25 foodie experiences including restaurants, bakeries and cafes in one place, just next to Square One.

Location: 100 City Centre Drive, Mississauga

Stop 4: Toronto

Approximate distance and travel time from Mississauga to Toronto: 18 miles (30 kilometres), 30 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 Lion King and Peter Pan to Clue, Live On Stage, 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 Lorde, Benson Boone and HAIM.

Location: 40 Bay Street, Toronto

Ontario Place Budweiser Stage

Neil Young, Mumford & Sons, Nelly, Alice Cooper and Cyndi Lauper 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 symphony this summer, from Brahms and Beethoven to the Bee Gees and Beyond.

Location: 60 Simcoe Street, Toronto

National Ballet of Canada

Don’t miss Anna Karenina at the Four Seasons Centre for the Performing Arts.

Location: 145 Queen Street West, Toronto

Toronto Blue Jays

Pro sports fans will not be disappointed in Toronto. 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 tra ibute 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 Neighborhood 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 showcasing the best new and emerging talent (June 11–15, 2025).

Pride Toronto

The largest Pride event in Canada, celebrating the 2SLGBTQI+ community for a full month, culminating in a festive parade (June 1–30, 2025).

Toronto Fringe Festival

Alternative, unconventional and entertaining theatre (July 2–13, 2025).

Honda Indy

A premier motorsports event at Exhibition Place (July 18–20, 2025).

Toronto Caribbean Carnival

An epic event showcasing the best of Caribbean culture, music and food (July 31–August 4, 2025).

Where to eat and drink

Foodie 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 over 7,500 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 foodie destinations like 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 14 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
• Blue Water Bridge, Port Huron, Michigan to Point Edward and Sarnia, Ontario

Before travelling, check border wait times.

Getting around

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.