Big-ticket entertainment, sports and nightlife in Windsor, Hamilton and Toronto

Experience the best of urban adventure across the border in Ontario, Canada.

A man and woman walking at sunset with cityscape in the background.

Downtown 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 food and nightlife.

And the best part? Your dollar goes a lot further in Ontario, Canada!

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:

Day 1 - 2: Windsor

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

Where to stay in Windsor

Caesars Windsor is a luxury casino resort with chic suites fitted with whirlpool tubs, and stellar river and city views. Resort amenities include fitness area, pool, restaurants, bar and entertainment.
Location:  377 Riverside Drive East, Windsor

Overlooking the Detroit River, Best Western Plus Waterfront Hotel is another great option for accommodations in the heart of downtown Windsor.
Location: 277 Riverside Drive West, Windsor

Things to do in Windsor

Local history

The historic distillery is now home to J.P. Wiser’s Canadian Whisky, among other renowned labels and offers a 90-minute J.P. Wiser’s Experience tour that explores the storied history of Canadian whisky along with a tasting session.
Location: 2072 Riverside Drive East, Windsor

Shopping and entertainment

Try your luck at Caesars Windsor Casino, from table games like Blackjack, Roulette and Poker to over 2,000 slot machines.
Location: 377 Riverside Drive East, Windsor

The Colosseum is Caesars Windsor’s state-of-the-art entertainment venue for big-ticket live music, comedy and more.
Location: 377 Riverside Drive East, Windsor

For live music and a fun, friendly vibe, check out The Backstage at Players Sports Club.
Location: 1530 Langlois Avenue, Windsor

Shop W.E. Made It for locally made apparel, jewellery, home accessories and art.

Designed by the renowned Thomas McBroom, Ambassador Golf Club is an 18-hole, 71 par championship golf course and driving range.
Location: 1025 Sprucewood Avenue, Windsor

Where to eat and drink in Windsor

Taste the French toast, waffles and omelets at The Twisted Apron in the Walkerville neighbourhood or kick start your day with coffee and a pastry at Anchor Coffee House.
Locations:
The Twisted Apron at 1833 Wyandotte Street East, Windsor
Anchor Coffee House at 543 Lincoln Road, Windsor

Mezzo Ristorante & Lounge has been voted the best restaurant as well as the most romantic dining in Windsor, for its food, atmosphere and entertainment. Plus, they make great gourmet take-out boxes.
Location: 804 Erie Street East, Windsor

Enjoy upscale dining with an elevated view at Fourteen Restaurant Sky & Lounge overlooking the city and river. Be sure to make reservations well in advance, this is a very popular spot.
Location: 100 Ouellette Avenue, Windsor

Discover Windsor’s passion for pizza, including Windsor-style pizza with shredded pepperoni, local Galati mozzarella and canned mushrooms at Terra Cotta Pizzeria.
Location: 318 Pelissier Street, Windsor

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

Day 3 - 4: Hamilton

  • Approximate distance and travel time: 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

Hamilton’s C Hotel by Carmen’s offers a European-inspired boutique experience with themed room décor and an onsite Italian restaurant.
Location: 1530 Stone Church Road East, Hamilton

The Pearle Hotel & Spa is 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

Elite sporting events and big-ticket artists like Shania Twain are billed to perform at FirstOntario Centre, Hamilton’s largest live music and entertainment venue.
Location: 101 York Boulevard, Hamilton

The Canadian Football League season runs into October, with Hamilton’s pro team Hamilton Tiger-Cats playing at the Tim Hortons Field stadium.
Location: 64 Melrose Avenue North, Hamilton

Enjoy a laugh at Levity Comedy Club & Lounge 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, a 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

The breakfast and coffee at Saint James Espresso Bar and Eatery will fuel your day.
Location: 170 James Street North, Hamilton

If you’re in the mood for a leisurely brunch, check out The Electric Diner in Hess Village, the weekend brunch at The French Bistro or experience the ultimate, chef-curated Sunday brunch spread at the Ancaster Mill (reservations recommended).
Locations:
The Electric Diner at 96 George Street, Hamilton
The French at 37 King William Street, Hamilton
Ancaster Mill at 548 Old Dundas Road, Ancaster

Satisfy your cravings for tacos and tequila at The Mule.
Location: 41 King William Street, Hamilton

A seasonal, west coast-inspired small plate menu is perfect for sharing at Berkley North. Closed on Tuesdays.
Location: 31 King William Street, Hamilton

The chef’s Italian roots and love of local shine at Born & Raised, open Thursdays to Saturdays, with a late-night menu including $2 oysters at 10:30 p.m.
Location: 224 James Street North, Hamilton

Award-winning Quatrefoil Restaurant in nearby Dundas is a must for foodies. Refined, contemporary cuisine is paired with a beautiful wine menu from Wednesdays to Saturdays.
Location: 16 Sydenham Street, Dundas

One of Hamilton’s flagship brewhouses, Collective Arts Brewing serves craft beer, cider and sparkling hard tea, along with a full calendar of arts and cultural events.
Location: 207 Burlington Street East, Hamilton

Day 5 - 6: Toronto

A large audience watches a band play at a concert.

  • Approximate distance and travel time: 45 miles (70 kilometres), 1 hour 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 is just 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

Enjoy cozy rooms, craft cocktails and skyline city views at Ace Hotel Toronto, one of Travel + Leisure’s top 100 new hotels in the world.
Location: 51 Camden Street, Toronto

Toronto’s landmark heritage hotel, Fairmount Royal York 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

The Park Hyatt Toronto sits 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

The St. Regis Toronto is 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

Attractions, museums and galleries

Visit the 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

Showcasing art, culture and natural history from around the world, the Royal Ontario Museum (ROM) is the largest in Canada.
Location: 100 Queen’s Park, Toronto

Explore the Art Gallery of Ontario (AGO), one of the largest art collections in North America as well as the Museum of Contemporary Art (MOCA).
Locations:
AGO at 317 Dundas Street West, Toronto
MOCA at 158 Sterling Road, #100, Toronto

For fans of the TV series Stranger Things, fulfil your fantasy to be a part of the adventure with the immersive Stranger Things: Experience at the Cinespace Marine Terminal Studio.
Location: 8 Unwin Avenue, Toronto

Theatre and stage

Check what’s on stage during your visit. From Harry Potter and Cursed Child at the Ed Mirvish Theatre to Hamilton at the Princess of Wales Theatre, Mirvish brings some of the best theatre productions to Toronto.
Locations:
Ed Mirvish Theatre, 244 Victoria Street, Toronto
Princess of Wales Theatre, 300 King Street West, Toronto

Get tickets well in advance for top crowd pleasers like Stevie Nicks, Lionel Richie, Sam Smith, Madonna and Ricky Gervais at the Scotiabank Arena and The Cure, TLC, Shaggy, En Vogue and Sean Kingston, Snoop Dogg and The National at the Ontario Place Budweiser Stage. Catch The Blaze or Marisa Monte performing at the Queen Elizabeth Theatre in the Exhibition Place Grounds.
Locations:
Scotiabank Arena, 40 Bay Street, Toronto
Ontario Place, 955 Lake Shore Boulevard West, Toronto
Queen Elizabeth Theatre, 190 Princes’ Boulevard, Toronto

The Toronto Symphony Orchestra will be performing Marvel Studios’ Black Panther in concert at the Roy Thomson Hall or enjoy the National Ballet of Canada’s Romeo and Juliet at the Four Seasons Centre for the Performing Arts.
Locations:
Roy Thomson Hall, 60 Simcoe Street, Toronto
Four Seasons Centre for the Performing Arts, 145 Queen Street West, Toronto

Sports and entertainment

Pro sports fans will not be disappointed in Toronto. Baseball season will be in full swing, so catch a Toronto Blue Jays game. The Canadian Football League season with the Toronto Argonauts runs until October.

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

Catch local comedians and rising comic stars at YukYuks Comedy Club or a comedy show at Comedy Bar 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:
YukYuks, 224 Richmond Street West, Toronto
Comedy Bar, 945 Bloor Street West, Toronto
Second City, 2800 Danforth Avenue, 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.

For what to do after dark, check out Toronto’s nightlife.

Festivals and celebrations

North by Northeast (NXNE): Canada’s answer to NXNW showcasing the best new and emerging talent (June 13-17).

Pride Toronto: The largest Pride event in Canada celebrating the 2SLGBTQ+ community (June 25).

Toronto Fringe Festival: Alternative, unconventional and entertaining theatre (July 5-16).

Honda Indy: A premier motorsports event at Exhibition Place (July 14-16).

Toronto Caribbean Carnival: An epic event showcasing the best of Caribbean culture, music and food (August 3-7).

Where to eat and drink in Toronto

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.

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

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

If it’s a view you’re after, you can’t beat the revolving dining room experience 350 metres (1,150 feet) up the CN Tower at 360 The Restaurant
Location: 290 Bremner Boulevard, Toronto

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. 
 

Extend your trip to Ontario with more road trip itineraries.

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Last updated: January 18, 2024

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