Woody's / Sailor

About this place Woody's / Sailor

Woody's and Sailor together form one of Toronto's most iconic gay bar spaces — twin venues sharing a building at 465 Church Street that have been running since 1989 and occupy a central place in the history of the Church-Wellesley Village. Woody's operates as the main bar, with a large front window onto Church Street, multiple bar areas, and a programming of themed nights, DJ sets, and the famous Best Chest and Best Ass contests that have been a Village institution for decades. Sailor, connected through the same building, has a slightly different character — darker, more cruisy, with a back-bar atmosphere. The combination of the two spaces under one roof gives the venue a range that most bars cannot match: you can have a drink at the Church Street-facing bar and watch the Village go by, or disappear into the Sailor end of the building for something more intimate. The bar won multiple Fab Magazine awards over the years and remains the standard against which other Village bars are measured.