Woody's / Sailor

Woody's is Toronto's most famous gay bar, a landmark that's anchored the heart of the Church-Wellesley Village since opening in June 1989. Connected inside to its equally beloved sister bar Sailor, together they form a massive, cavernous five-bar complex with nightly DJs, a pool table, dozens of video monitors, and drag performances and contests running nearly every night of the week: Tuesday's Openstage Cabaret, Wednesday's Hump Night Honeys, and the legendary weekend "Best Ass," "Best Chest," and "Best Legs" contests judged by crowd applause. Toronto Life once called it "the spiritual hub of the bar scene, and in many ways the gay community," and it's lived up to that for decades, a proud Pride Week sponsor whose fundraising has raised hundreds of thousands for the AIDS Committee of Toronto. A must-visit stop for any LGBTQ+ traveler and the place where many a drag star, Brooke Lynn Hytes included, got their start.