October 2026 Calendar of Events: Key West and the Florida Keys
October might be my favorite month to live in the Keys. The heat finally starts to ease, the water is still warm, stone crab season opens, and Key West throws its biggest party of the year. Whether you live here, are visiting, or are thinking about making the Keys home, here is what is happening across the island chain this month. Tap any event name below for details and tickets.
All Month Long
Oct. 1 to 31 | Key Largo and the Upper Keys
A month of prix-fixe menus at participating restaurants, plus chef-led events, tasting trolley tours and the Signature Dish Showdown. Presented by the Key Largo Chamber of Commerce. More info: tastethekeys.com
Through Oct. 31 | Keys-wide
A new Visit Florida Keys & Key West program with deals from participating hotels, restaurants, watersports operators and attractions. More info: Keys Season Deals
Thursdays, 1 to 6 p.m. | Truman Waterfront Park, Key West
Fresh produce, orchids and native plants, local foods and handmade goods on the waterfront. More info: keysartisanmarket.com
Early October
Saturday, Oct. 3, 3 to 8 p.m. | Southernmost Beach Resort, Key West
Key West's fall beer festival, hosted by the Key West Sunrise Rotary to benefit local student scholarships. More info: KeysTix
Friday to Sunday, Oct. 9 to 11 | Lower Keys
A classic Lower Keys community weekend. More info: Visit Florida Keys event page
Friday and Saturday, Oct. 9 and 10, doors at 6 p.m. | Marathon Community Theatre
Support one of the Middle Keys' favorite stages with a performance, hors d'oeuvres and auctions. More info: marathontheater.org
Saturday, Oct. 10, 5 to 7:30 p.m. | Old Seven Mile Bridge, Marathon
A free sunset gathering for America's 250th birthday, with live music, local bites and a sunset toast. There is no parking at the bridge, so use the free shuttle from 7 Mile Marina or the 33rd Street lot, or walk in from Knights Key. More info: Visit Florida Keys event page
Sunday, Oct. 11, 7 a.m. | Higgs Beach, Key West
The race starts and finishes at Higgs Beach. Expect street closures along the route until about 10:30 a.m. Register: RunSignup
Wednesday, Oct. 14, 7 to 10 p.m. | Tattoos & Scars Saloon, 512 Greene St., Key West
A breast cancer awareness block party benefiting Womankind, which helps provide mammograms for local women. More info: Womankind
Oct. 15 to 23 | Waterfront Playhouse, Key West
The award-winning rock musical returns as a live concert event to open the Waterfront's 88th season. Tickets: waterfrontplayhouse.org
Thursday, Oct. 15 | Keys-wide
The first fresh claws of the season start showing up at local fish markets and restaurants. Season rules: Florida Fish and Wildlife Conservation Commission
Oct. 15 to 18 | REEF Campus, Key Largo
An ocean-lover's festival with free marine science seminars, dives, social events and outdoor adventures. Register: reef.org/reeffest
Fantasy Fest: October 16 to 25
Key West's ten-day costume festival returns with the 2026 theme Musical Icons and Iconic Musicals. Much of the week is adults-only, but there are family-friendly events too (marked below). Here are the signature events. For the complete lineup of parties and times, see the official Fantasy Fest schedule.
Friday and Saturday, Oct. 16 and 17, noon to midnight | Petronia Street, Bahama Village
A free street party celebrating Key West's Bahamian roots, with Junkanoo, reggae and soca stages, island food and arts and crafts. More info: Fantasy Fest
Friday, Oct. 16, 6 to 9 p.m. | Coffee Butler Amphitheater
The kickoff, crowning the Fantasy Fest King and Queen after a months-long fundraising race for local nonprofits. More info: fantasyfest.com
Sunday, Oct. 18, Zombieland from 2 p.m., ride at 6 p.m. | Fort East Martello to Duval Street
Riders gather at Fort East Martello for body painting, food and a kids' zone, then thousands of costumed zombies roll into town. The 100 to 300 blocks of Duval close at the finish. Register: zombiebikeride.com
Monday, Oct. 19, 6 p.m. | Tiki House, 203 Duval St., Key West
A costumed evening race down Duval with a post-race party, benefiting Reef Relief. Register: RunSignup
Wednesday, Oct. 21, 5 to 9 p.m. | Coffee Butler Amphitheater
Costumed pets and their people compete for prizes. Free to watch. More info: fantasyfest.com
Thursday, Oct. 22, doors at 6:30 p.m. | Coffee Butler Amphitheater
The 43rd annual showcase of jaw-dropping headdresses, produced by the Key West Business Guild. Tickets: Key West Business Guild
Friday, Oct. 23, 5:30 p.m. | Old Town Key West
Known as the Locals' Parade, a costumed walk through Old Town that anyone can join. More info: fantasyfest.com
Saturday, Oct. 24, 7 p.m. | Duval Street
The main event, with floats and costumed groups rolling down Duval. More info: fantasyfest.com
Sunday, Oct. 25 | Bayview Park and La Te Da
Rides, games, crafts and a kids' costume contest at Bayview Park, then the official finale, "The Fat Lady Sings" Tea Dance at La Te Da. More info: fantasyfest.com
Late October
Tuesday, Oct. 27, 8 p.m. | Key West Theater
"The Crazy Uncle and His Sensible Niece," an evening of stand-up storytelling. Tickets: Key West Theater
Oct. 28 to Nov. 1 | Duval Street, Key West
Five days of island music from dozens of Trop Rock artists at venues you can walk between. More info: troprockers.com
Saturday, Oct. 31, 6 p.m. | Florida Keys Brewing Co., Islamorada
A Halloween night of raffles, music and brews benefiting I.CARE's coral restoration work. Come dressed as your favorite sea creature. More info: icareaboutcoral.org
A Few Local Tips
Plan around Fantasy Fest week. Old Town gets busy, parking is scarce, and parts of Duval close for the big events. Bikes are your friend.
Book early if you are visiting. Key West rooms fill up fast for Fantasy Fest.
House hunting while you are here? Mornings are a great time to tour homes, even during festival week. I am happy to set up showings around whatever you have planned. And I'll bring the glitter!
Watch the weather. Hurricane season runs through November 30, so keep an eye on the forecast and confirm event details before you go.
Thinking about making the Keys home? I would love to show you what living here is really like, festivals and all. Reach me at krystal@kskeywest.com, through my contact page, or on Instagram at @krystalsheehan.realtor.
Krystal Sheehan · Brokered by eXp Realty · Licensed in Florida
Event dates and times come from organizers, the City of Key West and Visit Florida Keys as of early October 2026 and can change. Please confirm with each event before you go.
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