Winchester Hotel 1888 -

Hotel and Bar

The imposing 3½-storey red brick Winchester Hotel  (built in 1888) with a 2½-storey red brick south wing, and the adjoining two-storey red brick Winchester Hall (built in 1881) are located at 531 Parliament Street, on the southeast corner of Parliament and Winchester streets in Cabbagetown.

The Winchester Hotel is a well-known local hotel noted for its distinctive Second Empire style and was designed by the noted architectural firm of Kennedy and Holland. In 1941, architect Benjamin Swartz oversaw alterations to the site, including the Art Moderne well-appointed interiors.

The space currently occupied by Tim Horton’s used to be one of the toughest drinking spots in the city, so tough that it’s nickname was “The Bucket of Blood”. Featherweight boxing champion and Cabbagetowner Albert “Frenchy” Bélanger once worked there as a waiter/bouncer.

Winchester Hall, at the back (east) of the hotel once housed a very popular jazz establishment where greats such as Billie Holiday and Charlie Parker entertained the crowds.

It is also said (likely an urban legend) that the American gangster Al Capone came to this spot during the days of prohibition to arrange for alcohol smuggling. He even would have asked to have a staircase built at the back of the building so he could escape as soon as the police showed up.

The Winchester Hotel and Winchester Hall are local landmarks that form part of the important collection of intact Victorian buildings in Cabbagetown. Its most recent restoration dates from 2020. It no longer is a hotel and now has various commercial and residential tenants.