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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.

This sight is featured in a self-guided walking tour of Toronto, Canada within the mobile app "GPSmyCity: Walks in 1K+ Cities" which can be downloaded from iTunes App Store or Google Play. Please download the app to your mobile phone or tablet for travel directions for visiting this sight. 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
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

Creating your own self-guided walk in Toronto is easy and fun. Choose the city attractions that you want to see and a walk route map will be created just for you. You can even set your hotel as the start point of the walk.
Toronto Islands Tour

Toronto Islands Tour

The Toronto Islands is a chain of islands located in Lake Ontario, comprising three major islands (namely: Center Island, Algonquin or Sunfish Island, and Olympic Island) and several smaller ones, which collectively represent a great recreation destination set in a peaceful and joyful environment. Other than a great panoramic view of Toronto, the islands offer a wealth of attractions. To acquaint...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 3.3 Km or 2.1 Miles
Distillery District Walk

Distillery District Walk

The architectural treasure of Toronto's Distillery District dates back to 1859 as the site of the largest distillery in the British Empire. This former industrial complex is now a National Historic Site of Canada and represents 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
Historic Buildings Walking Tour

Historic 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 of them, such as Gooderham, Daniel Brook Building, Massey Hall and others,...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 2.6 Km or 1.6 Miles
Toronto's Waterfront Walk

Toronto's Waterfront Walk

Toronto is located on the shore of Lake Ontario and it is more than obvious that the locals, as well as visitors to the city, cherish and admire the alluring views of the lake. 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. This walking tour will reveal all the pearls strewn along the quay....  view more

Tour Duration: 2 Hour(s)
Travel Distance: 3.7 Km or 2.3 Miles
Toronto Shopping Tour

Toronto Shopping Tour

There are many ways to enjoy shopping in Toronto. You can either walk along the oldest streets of the city, like Yonge street and visit the huge fancy shopping centers, or you can experience the atmosphere of the historic market of St. Lawrence. This tour has it all: from small unusual stores to big "all-mighty" malls. So don't hesitate to enjoy an authentic shopping experience by...  view more

Tour Duration: 1 Hour(s)
Travel Distance: 2.8 Km or 1.7 Miles
Cabbagetown Walking Tour

Cabbagetown Walking Tour

Once a small community of Irish immigrants and one of the poorest neighborhoods in Toronto, Cabbagetown is also one of the city's oldest districts, established in 1840, east of downtown. 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 is Amelia Street...  view more

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

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