Key West Festivals to Catch This Fall
Fall in Key West is packed with reasons to celebrate, and at Parrot Key Hotel & Villas, we look forward to this season every year. The island comes alive with vibrant festivals, bold flavors, and one-of-a-kind traditions that stretch from the end of summer through November, and Parrot Key puts you in the best location to experience it all, just a quick complimentary shuttle ride away from Duval Street and Smathers Beach.
It's an ideal time to visit, with something happening nearly every weekend, and our hideaway hotel beckons you to rest, relax, and recharge after a day full of Key West memory-making. From whimsical parades to epic races on the water, here's what we're circling on the calendar.
Savor Some Beers at BrewFest
August 28-30, 2025 | Various Locations, Key West
Key West BrewFest returns just before Labor Day, and it's all about celebrating craft beer, good company, and that laid-back island energy. The main tasting event takes place Saturday, August 30, but the days leading up to it are packed with creative ways to enjoy a cold one.
Kick things off with the Pool Floatie Chug & Race, a friendly competition at Southernmost Beach Resort where racing and beer drinking go hand in hand. Stick around for a grilled cheese and beer pairing trivia night or head to the Pineapple Pool Party on Friday for DJ sets, brewery samples, and a belly flop contest. With over 55 breweries represented, there's no shortage of new favorites to discover. BrewFest is casual, energetic, and a great way to experience the local scene.
Experience Magic at Fantasy Fest
October 17-26, 2025 | Duval Street, Key West
Fantasy Fest turns Key West into a bold and imaginative celebration each October. This 10-day festival is known for its elaborate costumes, creative parades, and packed event calendar. The 2025 theme, “Bedtime Stories & Magical Monsters,” promises plenty of playful twists on childhood favorites and fairy tale icons.
Expect offbeat highlights like the Zombie Bike Ride, where thousands of costumed riders take over the streets, and Tutu Tuesday, which transforms town into a parade of neon and sparkle. The Headdress Ball brings theatrical flair to the stage with dramatic costume artistry, while the Captain Morgan Masquerade March leads a free-spirited procession through Old Town.
Don't miss the grand finale: the Fantasy Fest Parade on Saturday night, when floats, music, and spectacle take over Duval Street in one of the most unforgettable nights of the year. Fantasy Fest is loud, colorful, and uniquely Key West.
Get Your Adrenaline Pumping at Key West World Championship
November 2-9, 2025 | Offshore from Key West
Every November, Race World Offshore brings high-speed action to the water for the Key West World Championship. Some of the world's fastest powerboats take over the coast, racing at speeds over 100 mph in this weeklong series.
Multiple race days, fan events, and viewing parties make this a big draw for locals and visitors alike. Boats whip past at breathtaking speeds, and the sound of engines fills the air. The energy builds toward the final championship races, with the best vantage points lining the harbor or at select waterfront spots around town. For those who like their vacation with a bit of an adrenaline rush, this is the event to catch.
Step into Holiday Spirit at the Waterfront Winter Wonderland
December 13-28, 2025 | Truman Waterfront Park, Key West
Waterfront Winter Wonderland transforms Truman Waterfront Park into a holiday-themed playground filled with twinkling lights, winter rides, and festive vibes with a tropical twist.
For two magical weeks in December, you can lace up some skates and hit the island's only ice rink, catch nightly “snowfall,” and take a spin on carnival rides like the Ferris wheel, carousel swings, and even a giant slide. The fun kicks off December 13 and runs through the 28, with highlights like the Running of the Elves 5K, Santa meet-and-greets (through Dec 22), and live music every night.
Don't miss the life-size snow globes and holiday selfie stations, perfect for your next holiday card. Whether you're sipping cocoa under the stars or checking names off your list at the local vendor village, this is a can't-miss December tradition in the heart of paradise.
Your Tropical Key West Homebase
Fall is one of our favorite seasons at Parrot Key Hotel & Villas. It's a time when the island buzzes with activity, creativity, and celebration during the day, and our hotel beckons you to an oasis of relaxation at night. After a day of fun, retreat to our tropical escape of spacious accommodations, lush landscaping, and home-like comforts.
Whether you're here for the wild costumes of Fantasy Fest, the easygoing fun of BrewFest, or the thrill of offshore racing, we're here to help you experience it all, comfortably and in true Key West style.