Upcoming Key West Festivals & Events: Oct 19 – Nov 17, 2025

Discover Key West’s Top Fall Festivals: Fantasy Fest, Offshore Boat Races & Film Festival

From October 19 through November 17, 2025, Key West transforms into a nonstop celebration of creativity, competition, and culture. Visitors can dive into the wild spectacle of Fantasy Fest, witness the adrenaline of Race World Offshore, and indulge in the cinematic elegance of the Key West Film Festival — three signature events that define autumn in paradise.

Fantasy Fest Key West 2025 — Continues Through Oct 26

The island’s biggest party is already in full swing! This year’s Fantasy Fest embraces the theme “Bedtime Stories & Magical Monsters,” turning Duval Street into a wonderland of fairytale characters and mystical creatures.

Can’t-miss events this week:

• Zombie Bike Ride — Sunday, Oct 19: Thousands of costumed riders glide along the Atlantic, ending in a sunset street party.

• Headdress Ball — Oct 23: A dazzling display of art, feathers, and flamboyance.

• Masquerade March — Oct 24: Locals take over Old Town in colorful costume parades.

• Fantasy Fest Parade — Oct 25 at 7 PM: The grand finale featuring floats, dancers, and dazzling light displays down Duval Street.

Visitors should plan ahead for street closures, book lodging early for the final weekend, and remember that while many daytime events are family-friendly, the late-night parties tend to be 21+ only.

Race World Offshore World Championship — Nov 2–9

Once Fantasy Fest wraps up, the roar of engines takes over. The Race World Offshore World Championship brings elite powerboat racers from around the globe to Key West’s sparkling waters. Fans can expect high-speed action, boat parades, and dockside events throughout the week.

Top viewing spots:

• Truman Waterfront Park – prime viewing for races and opening ceremonies.

• Harborfront venues and marinas – great for watching qualifying runs and social events.

This event perfectly balances the island’s high-energy pace with a sport-driven, family-friendly atmosphere.

Key West Film Festival — Nov 12–16

The Key West Film Festival 2025 shifts the spotlight from horsepower to artistry. Scheduled for November 12–16, this festival showcases independent films that reflect Key West’s inclusive and imaginative spirit. Screenings take place across multiple Old Town venues, with director Q&As, panel discussions, and special features celebrating diverse voices in cinema.

Visitors should purchase passes in advance, as key screenings sell out quickly. Combine an evening premiere with dinner at a waterfront restaurant for the ultimate “culture and cuisine” Key West experience.

Plan Your Visit Like a Local

• Oct 19–26: Enjoy Fantasy Fest’s final week of parades, parties, and costumes.

• Nov 2–9: Catch the world’s fastest boats at the Offshore World Championship.

• Nov 12–16: Wind down with cinematic flair at the Key West Film Festival.

• Book now — rooms fill fast during both Fantasy Fest and Boat Race Week.

• Stay updated — film schedules and event times may adjust closer to each date.

From sunset street parties to high-speed offshore races and award-winning films, Key West offers an unforgettable stretch of island excitement this season. Each event showcases a different side of paradise — thrilling, artistic, and always uniquely Key West.