Key West Bear Weekend
About This Event
Key West Bear Weekend is a five-day bear gathering at the end of October, timed to land on Halloween and to follow straight after Fantasy Fest. The home base is Island House, the men-only resort on Fleming Street, and the passes are sold through The Bear Mag.
Most daytime action happens at Island House: the Bear Soup pool parties, a firefighter-themed Hats & Hoses afternoon, happy hours and a Rocky Horror dive-in movie at the pool. Nights move to Duval Street and around it, with the Jocktober party at Bourbon St Pub and Bad Bear at Saloon 1 on Petronia Street. New for 2026 are bear yoga, a small craft cocktail tour and a boat cruise with BluQ.
Practical: the all-access pass covers everything except the add-ons. An Island House day pass is $50, and single covers run $10 to $20. The boat cruise is booked directly with BluQ. Island House rooms were close to sold out by August.
The 2026 edition ran 28 October to 1 November, with the farewell party at Island House on the Sunday. The 2027 dates hadn't been announced when we checked.
Where to stay during Key West Bear Weekend
via Stay22Schedule & Sub-Events
+ Add EventDetailed schedule coming soon.
Check the official website for the latest programme.
Practical Tips
Book Early for Passes and Accommodation
Weekend passes and tickets for marquee events like the Halloween Ball often sell out in advance. Similarly, accommodations, especially at Island House, should be booked well ahead of time.
Embrace the Relaxed Vibe
Key West Bear Weekend is known for its friendly and low-pressure atmosphere. Come as you are and enjoy the camaraderie and fun.
Pack for Pool Parties and Nightlife
Bring plenty of swimwear for the daytime pool parties and consider themed outfits or costumes for the Halloween Ball. Comfortable attire for exploring Duval Street is also recommended.
Videos
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