Winchester Hotel, Toronto

Winchester Hotel, Toronto

Winchester Hotel is a historic sight situated on the eponymous Winchester Street, which is one of the main arteries of Cabbagetown, Toronto well known for its Victorian Heritage architecture. The most famous building on the street, the hotel, in fact, is rather infamous and was once dubbed "The Bucket of Blood" for being one of the toughest drinking spots in the area. Featherweight boxing champion and local star, Albert “Frenchy” Bélanger, used to work the door here.

Also sometimes referred to as the Lake View Hotel, this imposing three-and-a-half storey red brick edifice, complete with a two-and-a-half storey south wing, features a distinctive Second Empire style. Built in 1888, it adjoins the equally renowned Winchester Hall, erected eight years earlier, and was designed by noted architects Kennedy and Holland who thus contributed a much needed low-rise lodge to the neighbourhood. In 1941, architect Benjamin Swartz oversaw alterations to the hotel’s interior, changing it to fit the tropes of the Art Moderne style.

Back in the days of Prohibition, the Winchester Hotel is said to have been used by Al Capone as the site for arranging alcohol smuggling into the United States. Reportedly, the American gangster even asked to have a staircase built at the back of the building to escape the police if they showed up.

Nowadays no longer a hotel, the place is still opened for business and accommodates various commercial tenants. Among them is the outlet of Tim Horton’s, Canada's largest quick service restaurant chain, specialized in coffee, doughnuts, and other fast food items. The most recent restoration of the building took place in 2005.

Want to visit this sight? Check out these Self-Guided Walking Tours in Toronto. Alternatively, you can download the mobile app "GPSmyCity: Walks in 1K+ Cities" from Apple App Store or Google Play Store. The app turns your mobile device to a personal tour guide and it works offline, so no data plan is needed when traveling abroad.

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Winchester Hotel on Map

Sight Name: Winchester Hotel
Sight Location: Toronto, Canada (See walking tours in Toronto)
Sight Type: Attraction/Landmark
Guide(s) Containing This Sight:

Walking Tours in Toronto, Canada

Create Your Own Walk in Toronto

Create Your Own Walk in Toronto

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Toronto Introduction Walking Tour

Toronto Introduction Walking Tour

Sprawling on the northwestern shore of Lake Ontario, the capital of the Canadian province of Ontario, Toronto, is a major metropolis renowned for its dynamic pace and high-rising skyline, incorporating both ultra-modern skyscrapers and historic architecture.

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Tour Duration: 2 Hour(s)
Travel Distance: 4.1 Km or 2.5 Miles
Toronto Islands Walking Tour

Toronto Islands Walking Tour

The Toronto Islands, otherwise simply known as “the Islands,” are a chain of islands in Lake Ontario, just off the coast of downtown Toronto. They include three major islands (namely: Centre Island, Algonquin or Sunfish Island, and Olympic Island) and several smaller ones. Collectively they are a great natural retreat set in a peaceful and joyful environment, which, apart from the panoramic...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 3.3 Km or 2.1 Miles
Toronto's Waterfront Walking Tour

Toronto's Waterfront Walking Tour

It is more than obvious that the locals of Toronto, as well as visitors, cherish and admire the alluring views of Lake Ontario on the shores of which the city is located. Toronto's waterfront is one of the most picturesque places for walking, but it is also a great destination for those in search of entertainment.

At the heart of this waterfront area stands Queen's Quay Terminal, a...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 3.7 Km or 2.3 Miles
Cabbagetown Walking Tour

Cabbagetown Walking Tour

Once a small community of Irish immigrants east of downtown and one of the poorest neighborhoods in Toronto, Cabbagetown is also one of the city's oldest districts, established in 1840. In 2004, it was declared a historic district and presently claims to be "the largest continuous area of preserved Victorian housing in North America". Attesting to this claim are the picturesque...  view more

Tour Duration: 1 Hour(s)
Travel Distance: 1.8 Km or 1.1 Miles
Historical Buildings Walking Tour

Historical Buildings Walking Tour

Once an Anglo backwater, today's Toronto is the cultural and economic hub of English-speaking Canada. The city's architectural beauty is supplemented by its historical richness, with some of the buildings dating back as far as the late 18th century. This self-guided tour invites you to explore the most prominent structures making up the historic heritage of Toronto.

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Tour Duration: 2 Hour(s)
Travel Distance: 2.6 Km or 1.6 Miles
Distillery District Walking Tour

Distillery District Walking Tour

Toronto's Distillery District is a trendy neighborhood and an architectural treasure dating back to 1859. Once the largest distillery in the British Empire, today this former industrial complex is a National Historic Site of Canada and a unique pocket of Victorian-era architecture, featuring the continent's best-preserved collection of cobblestone pathways and historic buildings housing...  view more

Tour Duration: 1 Hour(s)
Travel Distance: 0.8 Km or 0.5 Miles

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