October Is When Key West Comes Alive
There is October, and then there is October in Key West.
Fall may mean changing leaves and cooler temperatures elsewhere, but here on the island, October means costumes, creativity, Caribbean culture, outdoor celebrations, and one of the most anticipated months of the entire year.
Fantasy Fest may grab the headlines, but October offers much more. You can run down Duval Street, spend an afternoon at the Animal Farm, celebrate Bahamian heritage at Goombay, join thousands of zombies on bicycles, or simply enjoy an evening watching the sunset over Key West Harbor.
Whether you're planning a fall getaway or you're lucky enough to call Key West home, here's what's happening around the island this October.
🍺 October 3
Southernmost OktoBREWfest
October gets started with a Key West twist on a classic fall celebration.
Southernmost OktoBREWfest brings craft beer, food, music, and plenty of island atmosphere to South Beach. Instead of sweaters and chilly weather, expect ocean breezes and one of the most recognizable waterfront settings in Key West.
It's a fun way to kick off what quickly becomes one of the busiest and most colorful months of the year.
Date: October 3, 2026
Time: 3:00 PM to 8:00 PM
Location: South Beach
More Information:
Southernmost OktoBREWfest Information
🏃 October 3
Duval Mile Run
How often do you get the chance to run straight down one of America's most famous streets?
The Duval Mile Run turns Duval Street into a one mile racecourse through the heart of Old Town. It's fast, fun, and uniquely Key West, with a rolling street closure following participants along the route.
Whether you're racing for time or cheering from the sidewalk, this is a great way to experience Duval from a completely different perspective.
Date: October 3, 2026
Time: 5:00 PM to 7:00 PM
Location: Duval Street
More Information:
City of Key West Events Calendar
🏃 October 11
Southernmost Half Marathon & 10K
Runners get another opportunity to experience Key West on foot during the Southernmost Half Marathon & 10K.
Beginning and ending at Higgs Beach, the courses showcase some of the island's beautiful waterfront scenery with views of both the Atlantic Ocean and Gulf.
You can choose between the half marathon and 10K, making the event accessible to runners looking for very different challenges.
And really, there are worse places to cross a finish line than Key West.
Date: October 11, 2026
Time: 7:00 AM
Location: Higgs Beach
Registration & Information:
Southernmost Half Marathon & 10K
🐾 October 11 & 25
Monroe County Sheriff's Animal Farm
One of the area's most unusual hidden gems opens its gates twice this month.
The Monroe County Sheriff's Office Children's Animal Farm began as a refuge for animals in need and has grown into a home for rescued and surrendered domestic and exotic animals.
It's especially fun for families and offers a completely different Key West experience from the beaches and Duval Street.
Admission is free, although donations are always welcomed.
Dates: October 11 & 25, 2026
Time: 1:00 PM to 3:00 PM
Location: 5501 College Road
Official Website:
Monroe County Sheriff's Animal Farm
🎭 October 16 & 17
Goombay Festival
Before Fantasy Fest takes over Old Town, Goombay Festival brings the streets of Bahama Village to life.
This free, family friendly celebration honors the Caribbean and Bahamian influences that have played such an important role in Key West's culture and history.
Expect Bahamian and Caribbean inspired food, arts and crafts, street vendors, dancing, and live entertainment ranging from reggae to soca.
Goombay is more than a festival. It is a celebration of a part of Key West's heritage that continues to shape the island today.
Dates: October 16 & 17, 2026
Time: Noon to Midnight
Location: Bahama Village
More Information:
Goombay Festival & Fantasy Fest Schedule
🎭 October 16 through 25
Fantasy Fest
And then there is Fantasy Fest.
For 10 days, Key West becomes one enormous celebration of imagination, costumes, art, music, and the wonderfully unconventional personality that makes this island unlike anywhere else.
The theme for 2026 is "Musical Icons and Iconic Musicals," which should provide plenty of inspiration for some spectacular costumes.
Throughout the celebration you'll find events ranging from the Royal Coronation and Pet Masquerade to the Headdress Ball, Zombie Bike Ride, Street Fair, Costume Promenade, and the massive Fantasy Fest Parade.
Some events are family friendly, while others are intended for adults, so checking the official schedule before heading out is always a good idea.
Dates: October 16 through 25, 2026
Official Schedule:
Fantasy Fest 2026 Schedule
👑 October 16
Fantasy Fest Royal Coronation
Fantasy Fest officially gets underway with one of its longstanding traditions.
The Royal Coronation celebrates the candidates for King and Queen of Fantasy Fest while supporting the fundraising and community spirit behind the celebration.
The waterfront setting at Coffee Butler Amphitheater makes it an especially festive way to begin 10 days of Fantasy Fest.
Date: October 16, 2026
Time: 6:00 PM to 9:00 PM
Location: Coffee Butler Amphitheater
More Information:
City of Key West Events Calendar
🧟 October 18
ZombieLand & Zombie Bike Ride
This might be one of the most Key West events of the entire year.
The afternoon begins with ZombieLand at Fort East Martello, featuring a family friendly kids zone, bounce houses, food vendors, entertainment, and plenty of face and body painting.
Then, at 6:00 PM, thousands of zombies climb onto bicycles.
The annual Zombie Bike Ride sends an enormous procession of elaborately costumed riders toward downtown Key West, creating a spectacle that is almost as much fun to watch as it is to join.
If you've never experienced it, put this one on your Key West bucket list.
Date: October 18, 2026
ZombieLand: 2:00 PM to 6:00 PM
Zombie Bike Ride: 6:00 PM
Official Website:
Zombie Bike Ride 2026
🐕 October 21
Fantasy Fest Pet Masquerade
Fantasy Fest isn't only for humans.
The Pet Masquerade gives Key West's four legged residents their chance to get into the spirit with creative costumes and plenty of personality.
Pets and their humans take the stage together for one of the most entertaining and lighthearted events of Fantasy Fest week.
Date: October 21, 2026
Time: 5:00 PM to 9:00 PM
Location: Coffee Butler Amphitheater
More Information:
City of Key West Events Calendar
🎩 October 22
43rd Annual Key West Headdress Ball
The costumes get bigger as Fantasy Fest heads toward its final weekend.
The Key West Headdress Ball has become one of the celebration's signature events, showcasing elaborate handmade creations that can be theatrical, artistic, funny, glamorous, and occasionally enormous.
The 2026 event marks the 43rd Annual Headdress Ball.
It's one of those events where the creativity of Key West is on full display.
Date: October 22, 2026
Time: 6:30 PM to 11:00 PM
Location: Coffee Butler Amphitheater
More Information:
Key West Headdress Ball Information
🎨 October 23 & 24
Fantasy Fest Street Fair & Costume Promenade
By the final weekend of Fantasy Fest, Duval Street becomes the center of the celebration.
The Street Fair & Costume Promenade fills Old Town with food, art, crafts, entertainment, and thousands of people showing off their costumes.
This is when Fantasy Fest really spills into the streets and the entire downtown area becomes part of the experience.
Dates: October 23 & 24, 2026
Beginning: Noon
Location: Duval Street
Official Schedule:
Fantasy Fest 2026 Schedule
🎉 October 24
Fantasy Fest Parade
This is the big one.
The Fantasy Fest Parade is the centerpiece of the celebration and one of Key West's largest annual events.
Elaborate floats, incredible costumes, performers, music, and thousands of spectators fill Old Town for an evening that captures Fantasy Fest at its biggest and boldest.
For 2026, the parade begins at Truman Waterfront Park before making its way through Old Town.
If you're planning to attend, arrive early and expect downtown Key West to be extremely busy.
Date: October 24, 2026
Time: 7:00 PM
Location: Old Town Key West
Official Schedule:
Fantasy Fest 2026 Schedule
🎃 October 25
Children's Day
After 10 days of Fantasy Fest, Children's Day gives Key West families a celebration of their own.
Bayview Park fills with rides, games, food, arts and crafts, entertainment, and a children's costume contest.
It's a fun, family focused way to close out Fantasy Fest weekend and one of those community traditions that reminds you there is always another side to life in Key West.
Date: October 25, 2026
Time: Noon to 5:00 PM
Location: Bayview Park
More Information:
Children's Day 2026
🌅 Every Single Evening
Mallory Square Sunset Celebration
Even during one of Key West's busiest months, some traditions never change.
Every evening, people gather at Mallory Square to watch the sun disappear into the Gulf of Mexico.
You'll find street performers, musicians, local artists, food vendors, handmade crafts, and one of the most famous sunsets in Florida.
October brings plenty of elaborate events, but sometimes one of the best things to do is also the simplest.
Find a spot by the water and watch another Key West day come to an end.
Official Website:
Mallory Square Sunset Celebration
Who You Work With Matters
October is a perfect example of why living in Key West is about so much more than owning a home here.
One weekend you're running down Duval Street. The next you're celebrating Bahamian heritage in Bahama Village. A few days later, thousands of zombies are riding bicycles across the island, and before you know it, Fantasy Fest has transformed Old Town into one enormous celebration.
These traditions, and the people behind them, are part of what makes Key West such an extraordinary place to call home.
Whether you're visiting and starting to wonder what life here might look like, searching for your next Key West property, or considering selling a home you've loved for years, having people beside you who truly understand the island makes a difference. Our team doesn't simply work in Key West. We're part of this community, and we're always happy to share the local knowledge, relationships, and experience that come with that.
Who You Work With Matters,
THE SPOTTSWOOD TEAM
Terri Spottswood, John Spottswood, Ted Stewart, Raymond Vazquez
305-432-4848
[email protected]
Truman & Co. Real Estate
