Windsor to Toronto: Entertainment, sports and dining adventure

Experience the best of urban food and fun across the border in Ontario, Canada.

Four people share a dish at Quetzal Toronto, a MICHELIN-starred restaurant.

Quetzal Toronto | Destination Ontario

Set out on a summer road trip to Toronto with stops in Windsor and Hamilton for big-name entertainment, pro-sports and epic cuisine and nightlife.

Suggested length of trip: 4-6 days

Border crossing information

Travellers 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.

Before travelling, check border wait times

Border crossing locations from Michigan into Canada include:
Detroit Windsor Tunnel, Detroit, Michigan to Windsor, Ontario
Ambassador Bridge, Detroit, Michigan to Windsor, Ontario


From casino entertainment to unique whisky tours, you’re guaranteed good food, drinks and fun in Windsor.

Where to stay in Windsor

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

Things to do in Windsor

Shopping and entertainment

Drinks of Walkerville Walking Tour

Whisky played a significant role in Windsor’s history. Enjoy whisky tasting followed by an informative tour of Walkerville and a flight of craft beer at Walkerville Brewery with Windsor Eats (on select weekends).
Location: 2072 Riverside Drive East, Windsor

Caesars Windsor Casino

Try your luck at table games like Blackjack, Roulette and Poker or on the over 1,700 slot machines.
Location: 377 Riverside Drive East, Windsor

The Colosseum

See what’s on at Caesars Windsor’s state-of-the-art entertainment venue for big-ticket live music, comedy and more.
Location: 377 Riverside Drive East, Windsor

The Backstage at Players Sports Club

Great venue for live music, awesome food and drinks and a fun, friendly vibe.
Location: 1530 Langlois Avenue, Windsor

W.E. Made It

Shop for locally made apparel, jewellery, home accessories and art at participating locations.

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

Where to eat and drink in Windsor

The Twisted Apron

Enjoy delicious French toast, waffles and omelettes in the Walkerville neighbourhood.
Location: 1968 Wyandotte Street East, Windsor

Anchor Coffee House

Kickstart your day with fresh coffee and a pastry.
Location: 543 Lincoln Road, 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:


Approximate distance and travel time from Windsor to Hamilton: 185 miles (300 kilometres), 3 hours

No longer a hidden gem, Hamilton, the ‘City of 100 Waterfalls’ also boasts art, culture and cuisine.

Where to stay in and around Hamilton

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

Things to do in Hamilton

Culture, sports and entertainment

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

Levity Comedy Club & Lounge

Enjoy a laugh with regular local and renowned stand-up comedians scheduled, amateur open mic nights and great drinks and sharable food menu.
Location: 120 King Street West, Hamilton

Dundurn Castle

This National Historic Site is an impressive heritage home and garden of a former premier built in the 1830s that’s been carefully restored and is open for tours and events.
Location: 610 York Boulevard, Hamilton

Where to eat and drink in Hamilton

Saint James Espresso Bar and Eatery

Fuel your day with a delicious breakfast and coffee.
Location: 170 James Street North, Hamilton

The Electric Diner

If you’re in the mood for a leisurely brunch, head to the Electric Diner in  Hess Village or Lister Block.
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

Ancaster Mill

Experience the ultimate, chef-curated Sunday brunch spread (reservations recommended).
Location: 548 Old Dundas Road, Ancaster

The Mule

Satisfy your cravings for tacos, tamales and tequila.
Location: 41 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


Approximate distance and travel time from Hamilton to Toronto: 45 miles (70 kilometres), 1 hour and 15 minutes

Revel in Canada’s most multicultural and vibrant city. Experience top theatre, pro-sports, entertainment and accommodations in Toronto.

Where to stay in Toronto

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

Fairmount Royal York

Toronto’s landmark heritage hotel is within walking distance of most downtown sports and nightlife. Valet parking is available at the east entrance and self-parking options nearby.
Location: 100 Front Street West, 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 electric car charging station provided.
Location: 325 Bay Street, Toronto

Things to do in Toronto

Attractions, museums and galleries

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

Little Canada

Experience an immersive journey through miniature Canadian cities such as Niagara, Ottawa and Toronto.
Location: 10 Dundas Street, East, 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

Theatre and stage


Check what’s on stage during your visit. From Wicked at the Princess of Wales Theatre to Mean Girls at the Royal Alexandra Theatre, Mirvish brings some of the best theatre productions to Toronto.
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 Janet Jackson, Snoop Dogg, Niall Horan, Missy Elliot and Billy Idol.
Location: 40 Bay Street, Toronto

Ontario Place Budweiser Stage

Neil Young, Avril Lavigne, Orville Peck, Alanis Morisette, Hootie & the Blowfish and Norah Jones will be performing this summer.
Location: 909 Lake Shore Boulevard West, Toronto

Queen Elizabeth Theatre

Catch Hermanos Gutiérrez or Keane at the Queen Elizabeth Theatre in the Exhibition Place Grounds.
Location: 190 Princes’ Boulevard, Toronto

Toronto Symphony Orchestra

This season, The Toronto Symphony Orchestra will perform FREEDOM! A Tribute to Aretha Franklin at the Roy Thomson Hall.
Location: 60 Simcoe Street, Toronto

National Ballet of Canada

Enjoy Don Quixote at the Four Seasons Centre for the Performing Arts.
Location: 145 Queen Street West, Toronto

Sports and entertainment

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 with the 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 tribute to its greatest players.
Location: 30 Yonge Street, Toronto

Comedy clubs

Catch a comedy show with local comedians and rising comic stars like Josh Johnson 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).
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 takes place June 12–16, 2024.

Pride Toronto

The largest Pride event in Canada celebrating the 2SLGBTQI+ community on June 30, 2024.

Toronto Fringe Festival

Enjoy alternative, unconventional and entertaining theatre, July 3–14, 2024.

Honda Indy

This premier motorsports event is held at Exhibition Place, July 19–21, 2024.

Toronto Caribbean Carnival

An epic event showcasing the best of Caribbean culture, music and food, August 1–5, 2024.

Where to eat and drink in Toronto

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. 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.

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

Make it an extra memorable date and book reservations at one of Toronto’s recently awarded restaurants.

Food tours

Get the inside scoop from local experts at Culinary Adventure Co. or Tasty Tours Toronto on a themed culinary tour.


For trip planning support, connect with one of our travel counsellors who can help you build your road trip itinerary.

Discover more great Ontario road trip ideas.

Last updated: May 2, 2024

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