Calendar of Events
Oct21Live at Sunset Pier – DJ Scott Gerke
Join us at the Sunset Pier for live music over the water as you enjoy tropical libations and delicious bites.
Date: Daily: October 21 - 24, 2026
Time: 1:00 pm - 4:00 pm
Location: Sunset Pier
Oct21Live at Sunset Pier – Jerico Rockability Quartet
Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.
Date: October 7, 2026 / October 14, 2026 / October 21, 2026
Time: 6:00 pm - 8:00 pm
Location: Sunset Pier
Oct22Savor the Season
Celebrate Sober October with Ocean Key Resort and Best Day Brewing.
Date: October 1, 2026 - October 31, 2026
Time: All day
Location: Sunset Pier
Oct22Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.
Date: May 14, 2026 - December 31, 2026
Time: Thursday evenings (varies by operator)
Location: Off-Site (Key West – walking or trolley tour)
Oct22Fantasy Fest
Fantasy Fest turns Key West into a spectacle of masked processions, parties, contests and dances attended by tens of thousands.
Date: October 16 -25, 2026
Time: Varies by event
Location: Key West (multiple venues)
Oct22Romance at Hot Tin Roof
Add some romance to your dining experience with a chilled bottle of Lallier Reserve Brut champagne and your table decorated with rose petals
Date: May 14, 2026 - December 31, 2026
Time: Thursday's, During Hot Tin Roof dining hours
Location: Hot Tin Roof
Oct22Ocean Key Lime Bike Tour
Sightseeing the Key West way with a leisurely island bike tour that can be done in flip flops!
Date: May 14, 2026 - December 31, 2026
Time: Thursday's, 10:00 am – 12:00 pm
Location: Key West (guided bike tour)
Oct22Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - December 31, 2026
Time: Thursday's, 2:00 pm – 7:00 pm
Location: Truman Waterfront
Oct22Live at Sunset Pier - Reggae Lou & The Kind Buds
Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.
Date: Thursdays: October 1 - October 29, 2026
Time: 6:00 pm - 8:00 pm
Location: Sunset Pier
Oct23Halloween Cocktails
Treat yourself to hauntingly delicious cocktails this spooky season at Hot Tin Roof.
Date: October 23, 2026 - October 31, 2026
Time: All day
Location: Hot Tin Roof
