Winchester Hotel - Cabbagetown

Winchester Hotel

Located in the heart of Cabbagetown, the Winchester Hotel was first built in 1888, and is one of Toronto’s oldest surviving structures.




The property contains two sections, the eastern 2 and half story Winchester Hall (formerly known as the Lakeview Hotel) built in 1880, and the adjoining 3 and a half story Winchester Hotel built in 1888. The hotel has a dark history, colloquially referred to as the “Bucket of Blood”, due to the numerous fights which occurred in and around the property.

The Winchester in 1954


New Beginnings

Over the next century the building underwent various alterations and tenants, but served as a cornerstone of the Cabbagetown community all the while.


By 2000, the building was in need of some TLC. While the building had a steady tenant, the Winchester Pub, lack of proper maintenance meant it was far from¬†perfect. A revitalization effort began in 2004 to return the site to its original glory.¬†About ten years later, construction completed and the Winchester looked better than ever. Now home to Kingyo, a Japanese restaurant, Planet Paradise, a vape lounge, and a Tim Horton’s, the Winchester now serves as the meeting place for a new generation.




Open It!