Key West Headdress Ball
2026-10-22 | Truman Waterfront Park, Key West, FL, United States
Key West Headdress Ball

The Key West Business Guild proudly presents the 43rd Anniversary Edition of the Headdress Ball — one of the most anticipated events of the Fantasy Fest Celebration, on Thursday, October 22, 2026, at the Coffee Butler Amphitheater at Truman Waterfront Park. Doors open at 6:30 PM, with the show beginning at 8:00 PM.

This unforgettable evening of creativity, glamour, and entertainment will once again be hosted by legendary Key West entertainer Randy Roberts, with music by WEOW’s RudeGirl. Guests will experience an extraordinary showcase as twelve to fifteen contestants unveil their stunning Headdress creations, judged from the shoulders up, all competing for the coveted $5,000 grand prize.
The evening will also feature performances by some of Key West’s most celebrated local talent, making this a true highlight of Fantasy Fest. Guests can enjoy full bar service, specialty wines, and the convenience of preordered food delivered directly to their tables.
Ticket options: (does not include fees)
• Premium Table for 4 — $400( includes a bottle of wine of your choice, non-alcoholic drink option, or bucket of beer)
• VIP Table for 4 — $290
• Chair Seating — $40
• General Admission (Grass Seating) — $30

The Headdress Ball continues to celebrate the vibrant spirit, creativity, and welcoming atmosphere that makes Key West one of the world’s most unique destinations for visitors from all walks of life.

For more information, or to enter the Headdress Contest, visit gaykeywestfl.com/headdress-ball or call 305-294-4603.
This event always sells out, so book your tickets early.

Key West Food and Wine Festival
2027-01-27 - 2027-01-31 | Key West, Florida, Key West, FL, 33040, United States
2027 Key West Food and Wine Festival
1/27/26 – 1/31/27
5 continents~5 wines~5 stories~5 Dishes~5 chefs

Welcome to Key West Food & Wine Festival 2027

A curated journey through the culinary heritage of five continents, featuring world-renowned chefs, their signature dishes, and the legendary wines that define their regions.
This journey spans five continents with iconic wines, each telling a story of terroir, history, and culture:
Africa: a smoky Pinotage,
Europe: a structured Bordeaux,
South America: a robust Malbec from Mendoza,
Oceania: a vibrant Marlborough Sauvignon Blanc,
North America: a cool-climate Pinot Noir from Oregon.

The Key West Food and Wine Festival is recognized as one of the best food and wine festivals in the country by the Travel Channel. If you’re a foodie, Key West is the place to be in January. With many unique events, held at spectacular island locations, this is an opportunity to enjoy a wide variety of wines and cuisine, with waterfront tastings, wine/food pairings, and local events around Key West.
Information courtesy of the Key West Food & Wine Festival – see their website for more details!

Florida Keys Seafood Festival
2027-02-13 - 2027-02-14 | Truman Waterfront Park, Key West, FL, United States
Florida Keys Seafood Festival
FEBRUARY 13-14, 2027

Two Days of Seafood, Music & Family Fun!

Join us for the 20th Annual Florida Keys Seafood Festival at Truman Waterfront Park in Key West. For just $10 admission, enjoy two full days of fresh, local seafood, live music, activities, and the vibrant island atmosphere that make this festival a Florida Keys favorite. This family-friendly event not only highlights the freshest local catch but also showcases the dedication of our commercial fishermen and women.

On the Menu…

Fried Fish baskets or platters with slaw and black beans & rice, Fried Shrimp basket, Grilled Spiny Lobster Platters, Stone Crab Claws with key lime mustard sauce, peel and eat Key West Pink Shrimp with cocktail sauce, Smoked Fish Dip with crackers, Creamy Lobster Bisque, Bahamian style Conch Chowder, Conch Ceviche, & Conch Fritters. Hot dogs and hamburgers also will be for sale. Beverages include beer, wine, rumaritas, rum runners, water, soda and coffees. Desserts include Key Lime Pie and other homemade treats.
Activities

Raffle to win $250 in seafood shipped to your home!
Great shopping and art
Fantastic entertainment all day

Children’s Eco Discovery Zone with activities

Adult beverages, beer, wine, frozen rumaritas with First Legal Rum
Event t-shirts, mugs and authentic lobster trap buoys for sale

The Florida Keys Seafood Festival directly supports the mission of the Florida Keys Commercial Fishermen’s Association (FKCFA), an organization dedicated to protecting, promoting, and sustaining the Keys’ commercial fishing community.

CREDIT: http://www.floridakeysseafoodfestival.com/
Information / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.)

Key West Songwriters Festival
2027-04-28 - 2027-05-02 | Key West, Florida, Key West, FL, 33040, United States
The Key West Songwriters Festival.
4/28/27 – 5/2/27

The Key West Songwriters Festival is the largest festival of its kind in the world, and known as a career starter for top country talent. The festival has kicked off the careers of household names such as Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy Houser and Maren Morris. In its 27th year, KWSF has grown into a top destination for music lovers who flock to Key West for five days and nights of live music and storytelling from veteran songwriters and the next big hit-makers.
