Windsor to Toronto fall road trip: Epic entertainment, sports and nightlife

Windsor

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

J.P. Wiser’s Experience Tour: Visit the historic Hiram Walker & Sons Distillery, now home to J.P. Wiser’s Canadian Whisky, among other renowned labels and explore the storied history of Canadian whisky along with a tasting session.
Location: 2072 Riverside Drive East, 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

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

Toronto

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 7:00 p.m. to 7:00 a.m.
Date: September 23, 2023

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.

Just For Laughs Toronto: Some of today’s funniest comedians take to the stage during this famous festival of comedy.
Dates: September 21-24, 2023
Locations: Various venues across the city

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.
Dates: November 3-12, 2023
Location: Exhibition Place, Toronto

Mirvish: Home to some of the best theatre productions to Toronto. Check what’s on stage during your visit.
Locations:
Ed Mirvish Theatre, 244 Victoria Street, Toronto
Princess of Wales Theatre, 300 King Street West, Toronto

Scotiabank Arena : Get tickets well in advance for shows like Shania Twain, Queen & Adam Lambert, Drake, SZA, Wu-Tang Clan and Aerosmith.
Location: 40 Bay Street, Toronto

Where to eat and drink in Toronto

Toronto restaurants, cafes and eateries don’t disappoint: 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: Toronto is the first Canadian city to be recognized in the MICHELIN Guide with over a dozen restaurants starred.

MICHELIN 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: Parliament Street to Cherry Street, south of Front Street East, 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: East of Avenue Road and north of Bloor Street East, Toronto

Ossington Strip: This west side street has flourished into a hip foodie destination with cool brewpubs, bars and bistros.
Location: Ossington Street

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