Upcoming Key West Events
Here is a look at great upcoming events in Key West this month.
Key West Art & Craft Festival — February 21 & 22, 2026
Truman Waterfront Park. February 21–22, 10am–5pm. Key West's largest outside art show is sponsored by the Key West Art Center, a non-profit community arts organization and the oldest art gallery in Key West. This will be the third year the combined art & craft show will be on the Quay in beautiful Truman Waterfront Park in Old Town Key West. It is a stunning waterfront setting with a beautiful park on one side and the water on the other, along with lots of parking for patrons. This is a juried show.
Taste of Key West 2026 — March 23rd, 6:00–9:00 PM
Taste of Key West 2026 returns on Monday, March 23, 2026, transforming Truman Waterfront Park into the island's most anticipated culinary celebration from 6:00–9:00 PM. Now more than three decades strong, this iconic Key West food festival brings together 40+ celebrated restaurants, 200+ wines, craft beers, and spirits, and thousands of food lovers for a sunset-drenched evening along the harbor.
Guests wander freely from tasting station to tasting station, sampling dishes that reflect the region's coastal influence and global inspirations. The event's beverage program features generous pours of acclaimed wines, locally brewed beers, and curated spirits, with live music and island rhythms throughout the park.
Ticket options: General admission allows guests to purchase $1 tasting tickets. The popular $75 Two for Taste package includes 60 tasting tickets and two souvenir glasses or plates. The $150 VIP Pass delivers unlimited food and wine, access to a climate-controlled VIP tent, butler-passed bites, and a private lounge with sunset views.
Beyond the food and festivities, Taste of Key West serves a greater purpose — a major fundraiser supporting AH Monroe's 40th-anniversary initiatives, with proceeds benefiting health clinics, affordable housing, and recovery programs throughout the Florida Keys.
Key West Songwriters Festival 2026 — April 29 – May 3, 2026
The 30th Annual Key West Songwriters Festival returns April 29 – May 3, 2026, transforming Key West into a walkable stage filled with live storytelling and acoustic collaboration. Recognized as one of the world's largest gatherings dedicated to songwriters, the festival brings together more than 200 artists performing across theaters, waterfront stages, bars, and outdoor listening rooms.
Throughout the week, the festival blends intimate songwriter rounds with full-scale evening concerts. Many daytime events remain free to attend, while select headline shows are ticketed. Signature in-the-round performances take place on Friday, May 1 from 5:30–9:30 PM and Sunday, May 3 from 12:00–4:45 PM. Celebrating its 30th year, the event continues merging Nashville's songwriting culture with the relaxed energy of Key West.