The Key West
Annual Headdress Ball 2027

The Key West Annual Headdress Ball 2027

The Key West Headdress Ball is the premier gay and lesbian event of the Fantasy Fest celebration.

• Visiting for the event? If you are looking for a last minute deal or want a larger hotel with great amenities, check out the Key West Marriott Beachside. Alternatively try Alexander’s Guesthouse  for a unique gay escape.

The 2027 Annual Headdress Ball

• Next edition: Thursday, October 28, 2027.
• Doors open at 6:30 pm. Show runs from 8 pm to approximately 11 pm.
• Venue: Coffee Butler Amphitheater, Truman Waterfront Park, 21 East Quay Road, Key West.
• Host: Randy Roberts, one of Key West’s best-known entertainers.
• Competition: Approximately 12 to 15 contestants competing across six award categories.
• Total prize fund: $6,000.
• Book tickets through the official Headdress Ball website.

What Makes the Headdress Ball Special?

• The Headdress Ball is part costume competition, part cabaret and part celebration of Key West’s famously unconventional personality.
• Each contestant takes to the stage to reveal an original creation, often involving months of design and construction. The judging focuses on the headdress itself, from the shoulders up, rather than the complete outfit.
• Expect oversized feathers, sculptural designs, imaginative characters, elaborate lighting and dramatic reveals. Some entries are humorous, others are remarkable pieces of wearable art.
• Unlike the street parties that dominate much of Fantasy Fest, this is a seated performance where guests can appreciate the craftsmanship, presentation and personalities behind each creation.

The Headdress Competition

Final Categories and Theme to be confirmed. Expect the following:

Award	Prize	What the Judges Look For
Head Above the Rest	$2,500	Overall artistic excellence, originality, craftsmanship and presentation.
Spirit of Fantasy Fest	$1,000	The creation that best interprets the festival’s official theme.
Pretenders in Paradise	$750	A complete costume and headdress that work together as one artistic creation.
Glow Getter	$500	Imaginative use of lighting, LEDs and illuminated effects.
Dream Team	$500	Collaborative designs created by two or more artists.
Size Doesn’t Matter	$500	Smaller designs that make an exceptional visual impact.

Tickets and Seating

Choose your ticket according to how you want to experience the show.

• General admission: $30 for grass seating.
• Reserved chair seating: $40.
• VIP table for four: $290.
• Premium table for four: $400, including a choice of wine, beer or non-alcoholic drinks.

Booking fees are additional. Full bar service, specialty wines and advance food orders are available.

The event regularly sells out, so reserve your preferred seating early.

The Venue: Coffee Butler Amphitheater

The Coffee Butler Amphitheater sits within Truman Waterfront Park, on the western side of Key West’s Old Town.

The open-air venue is particularly suited to the Headdress Ball, giving competitors a large stage for their elaborate creations while allowing guests to enjoy an evening beneath the stars.

• A permanent covered performance stage accommodates the runway presentations and entertainment.
• The audience area combines reserved seating with a grass lawn for general admission.
• The surrounding waterfront park provides a more spacious setting than the busy streets of Duval.
• The amphitheater is close to Fort Zachary Taylor Historic State Park and within reach of Old Town’s hotels and restaurants.

Before and After the Ball

Start with an early drink on Duval Street, but leave enough time to reach the amphitheater before the show.

• La Te Da – 1125 Duval Street. A classic Key West venue combining a restaurant, piano bar and cabaret. Particularly appropriate for an evening celebrating theatrical performance and costume design.
• 801 Bourbon Bar – 801 Duval Street. Famous for Sushi and the 801 Girls, with drag shows, karaoke and a longstanding place in the island’s LGBTQ+ nightlife.
• Bourbon Street Pub – 724 Duval Street. A popular gay bar with male dancers, music and a sociable crowd. Its adjoining garden and pool area are especially popular during Fantasy Fest.
• SideBar Key West – 504 Angela Street. A late-night gay dance bar for guests who want to continue celebrating after the awards.

Check the individual venues’ Fantasy Fest programmes before making plans, as special events and admission arrangements can change.

Where to Stay

Stay in Old Town Key West, preferably near Duval Street or the Truman Waterfront. You’ll be able to explore most of Fantasy Fest on foot without depending on taxis.

These four highly rated boutique properties offer different advantages, from peaceful tropical gardens to immediate access to the island’s nightlife.

• Orchid Key Inn, Adults Only – Our first choice for a stylish Key West stay. Located directly on Duval Street, with elegant contemporary rooms, a heated pool, hot tub and intimate cocktail bar. Excellent for exploring the gay nightlife on foot.
• Almond Tree Inn, Adults Only – A beautifully maintained boutique hotel on Truman Avenue, just off Duval Street. Tropical gardens surround the pool and hot tub, while breakfast and a daily happy hour add to its appeal.
• Simonton Court Historic Inn & Cottages – A collection of historic cottages and guest rooms arranged around secluded gardens and four swimming pools. Choose it for traditional Key West character, a peaceful atmosphere and easy access to the northern end of Duval Street.
• Santa Maria Suites Resort – A sophisticated all-suite property near the southern end of Duval Street. Spacious accommodation with full kitchens, two heated pools and attractive landscaped grounds makes it especially suitable for friends attending Fantasy Fest together.

Key West Fantasy Fest

The Headdress Ball takes place during Fantasy Fest Key West, running from Friday 16th October to Sunday 25th October 2026.

The wider festival includes street celebrations, themed costume contests, pool parties, drag performances and the spectacular Saturday night parade.

If you’re extending your visit, two highlights take place immediately after the ball:

• Friday 23rd October: Fantasy Fest Street Fair and Costume Promenade along Duval Street.
• Saturday 24th October: Fantasy Fest Parade, the festival’s signature evening spectacle.

Explore the official Fantasy Fest schedule for additional parties and performances.

Planning Your Visit

• Book accommodation early. Fantasy Fest is one of the busiest periods of the year in Key West.
• Arrive before the show begins, especially if you have reserved seating.
• General admission is on the grass, so dress comfortably and check the organiser’s rules for permitted items.
• The amphitheater is outdoors. Check the weather forecast and any event announcements before leaving your hotel.
• If you want to compete, visit the official contestant registration page.
• The Key West Business Guild has also published Thursday 28th October 2027 as the following year’s Headdress Ball date.