Key West Bear Weekend

Key West's bear community gets its own dedicated weekend every fall with Key West Bear Weekend, running Wednesday, October 28 through Sunday, November 1, 2026. Centered at Island House on Fleming Street, it's built around pool parties by day and themed nights after dark, with a reputation as one of the friendliest bear runs anywhere on the circuit.

What to expect

Days run around Island House's "Bear Soup" pool parties, along with a firefighter-themed pool party, a clothing-optional send-off pool party on the final day, and new-for-2026 additions like bear yoga and a craft cocktail tour. Nights bring a Halloween Ball, a mandatory jockstrap party, and a Rocky Horror Picture Show dive-in movie, with the Mr. Key West Bear contest as one of the weekend's marquee competitions. Clothing-optional boat cruises with BluQ round out the daytime options for anyone wanting time on the water between parties.

History and legacy

Key West Bear Weekend has run for years as one of two dedicated bear gatherings organized by the same team behind Key West's WOOF Week each spring, giving the island's bear community two distinct annual weekends rather than folding it into the broader Fantasy Fest or Pride calendars.

Getting there and staying

Island House anchors most of the weekend's daytime programming, making it a natural base, though several nearby adults-only guesthouses put you within easy walking distance of both the pool parties and Duval Street's bars. All Access Passes cover entry to the full slate of official parties, with an early bird rate available before prices rise closer to the event.

Plan your trip

Beyond the parties, Key West rewards a slower morning pace, snorkeling the reef, wandering Bahama Village for Cuban food, or visiting the Hemingway House, before the pool decks fill up in the afternoon. Passes and rooms both move fast for this one, so locking in early beats scrambling closer to October.