Part of the Gay Key West Guide — bars, events & things to do.
Wednesday, October 28 – Sunday, November 1, 2026
Island House & Duval Street, Key West
Key West Bear Weekend — a long Halloween-weekend gay men's bear getaway (Wed Oct 28–Sun Nov 1, 2026) based at the men-only Island House resort, where wristbands are collected. Bear Soup pool parties, the firefighter-themed Hats & Hoses party and the BEAR Pool Party by day; Bear Cruises on the BluQ catamaran, bear yoga and a craft-cocktail tour; a Rocky Horror dive-in movie, the Jocktober party at the Bourbon St Pub pool garden, Bad Bear with Cock Shock at One Saloon, and the Halloween Ball on Saturday night (the organizer lists the Birdcage Cabaret), closing with Sunday's tea and farewell parties. All Access Pass or per-event tickets.
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Wed, Oct 28
12 PM - 5 PM
Island House Key West, Key West
The opening pool party of Key West Bear Weekend 2026 at the Island House.
Wed, Oct 28
8:30 PM - 10:30 PM
Island House Key West, Key West
The poolside Rocky Horror dive-in movie at Key West Bear Weekend 2026.
Thu, Oct 29
10:30 AM - 2:30 PM
Blu Q Catamaran, Key West
Thu, Oct 29
2 PM - 6 PM
Island House Key West, Key West
Thu, Oct 29
9 PM - 1 AM
Bourbon Street Pub, Key West
The jockstrap dress-code party at Key West Bear Weekend 2026.
Fri, Oct 30
2 PM - 6 PM
Island House Key West, Key West
A themed clothing-optional pool party at Key West Bear Weekend 2026.
Let people know you're going, see who else is attending, and share the event with friends.
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