Winchester Hotel 1888 -

Hotel and Bar

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

It is a well-known local hotel noted for its distinctive Second Empire style and well-appointed interiors previously renovated to reflect the Art Moderne style.

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.

Al Capone

Al Capone

It is also said 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 property contains two buildings: Winchester Hall, built in 1880 and the adjoining Winchester Hotel, constructed in 1888 in two sections and designed by the noted architectural firm of Kennedy and Holland. In 1941, architect Benjamin Swartz oversaw alterations to the site, including the addition of the current hotel sign and the Art Moderne interior.

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 2005. It no longer is a hotel and now has various commercial and residential tenants.


The Winchester Hotel today.

The Winchester Hotel today.



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