Key West Arts, Music & Culture 2025–2026 Events Calendar

Calendar of Events: Key West Arts, Music & Culture 2025/2026

Key West Arts, Music & Culture Events 2025–2026

Key West’s arts, music, and cultural calendar is packed with vibrant festivals, parades, live performances, and culinary showcases from September 2025 through May 2026. From Fantasy Fest to Mile 0 Fest, each month brings signature island celebrations alongside ongoing traditions like Mallory Square’s nightly Sunset Celebration and live music at the Green Parrot.

September 2025 – Fall Kickoff

Womenfest Key West (Sept 3–7) fills the island with LGBTQ-friendly concerts, sails, pool parties, and socials. Art lovers can explore Walk on White (Sept 18, 6–9 pm) on White Street and First Fridays on Fleming (Sept 5, 6–9 pm) for gallery strolls. Weekly favorites include the Key West Farmers Market (Thursdays, 2–7 pm, Truman Waterfront), while the Key West Artisan Market reopens Oct 5 at Higgs Beach.

October 2025 – Fantasy Fest Season

The heart of Key West’s cultural calendar, Fantasy Fest, features the Goombay Festival (Oct 17–18, Noon–Midnight) in Bahama Village with Caribbean flavors and nonstop music. The Royal Coronation (Oct 17, 7 pm, Coffee Butler Amphitheater) crowns the new King & Queen of Fantasy Fest. ZombieLand & Bike Ride (Oct 19) adds spooky fun at Fort East Martello. The legendary Headdress Ball (Oct 23, 8 pm, Coffee Butler Amphitheater) showcases dazzling costumes, while Green Parrot triple sets energize Fantasy Fest week.

November 2025 – Film & Lights

Key West Film Festival (Nov 12–16) screens premieres and hosts filmmaker panels at Tropic Cinema and The Studios of Key West. First Thursday at The Studios (Nov 6) opens new exhibitions. Holiday cheer begins with Harbor Walk of Lights (Nov 27), illuminating the Historic Seaport through December.

December 2025 – Island Holidays

The KWAHS Exhibition “Shadow & Light: Island Contrast” (Dec 3–Feb 15, Custom House) highlights local artistry. Festive highlights include the Historic Inns Holiday Tour (Dec 5 & 12, 6–8 pm) and the Schooner Wharf Lighted Boat Parade (Dec 13, after dusk).

January 2026 – Festival Season

The year begins with the Key West Literary Seminar (Jan 8–11) and rock extravaganza RokIsland Fest (Jan 12–16). Seafood lovers flock to the Florida Keys Seafood Festival (Jan 17–18, Truman Waterfront, $10 admission). The Americana-inspired Mile 0 Fest (Jan 27–31, Coffee Butler Amphitheater + stages) and the indulgent Key West Food & Wine Festival (Jan 28–Feb 1) round out the month.

February 2026 – Arts & Cuisine

The Florida Keys Seafood Festival (Feb 14–15) returns, followed by the Key West Art & Craft Festival (Feb 21–22, Truman Waterfront Park, 10 am–5 pm). Monthly art strolls continue with Walk on White (Feb 19, 6–9 pm).

March 2026 – Culinary Delights

The culinary spotlight shines at Taste of Key West (Mar 23, 6–9 pm, Truman Waterfront Park) with bites from 50+ restaurants. First Fridays on Fleming (Mar 6) and Walk on White (Mar 19) keep the island arts scene thriving.

April–May 2026 – Music & Independence

Key West celebrates its quirky spirit with the Conch Republic Independence Celebration (Apr 18–27), highlighted by parades and the legendary “Sea Battle.” Food lovers return for Taste of Key West (Apr 20), followed by the internationally acclaimed Key West Songwriters Festival (Apr 29–May 3) featuring 200+ artists across 60+ shows.

Always On in Key West

The Mallory Square Sunset Celebration unfolds nightly with performers, food, and artistry two hours before sunset. Green Parrot Bar pulses with live music most nights and multiple-set weekends, while The Studios of Key West and KWAHS Museums host rotating exhibitions year-round.