Learn more about the spooky history of Key West this Halloween! Monroe County residents can take advantage of some of our tours and attractions for FREE when accompanied by a full fare adult paid guest with Hometown Pass!
Truman Waterfront Park, 21 E Quay Rd. (end of Southard St.)
Dates: October 1, 8, 15, 22, 29. Shop local every week with a wide mix of vendors.
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6:00 PM - 8:00 PM
Chef’s Encore Dinner Series at Key West Cooking Show
291 Front St., Ste 207
Join us for our Chef’s Encore dinner series with Executive Chef Keith St. Peter, hosted on the first Friday of each month. This month’s dinner is Chef’s Whimsy; there are no rules. No fixed theme. Just Executive Chef Keith St. Peter, left to his own devices to follow his instincts and see where the night takes him.
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Local’s Sunday
The first Sunday of the month offers Monroe County locals FREE admission to all Historic Tours of America attractions: Old Town Trolley Tours, Conch Tour Train, Ghosts & Gravestones, Key West Aquarium, Key West Shipwreck Treasure Museum, and Harry S. Truman Little White House.
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6:00 PM - 8:30 PM
Catch the Mania Trivia
Key West Cooking Show, 291 Front St., Ste 207
Dates: October 5, 12, 19, 26. Various themed trivia.
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1:00 PM - 3:00 PM
Monroe County Sheriff’s Animal Farm
5501 College Rd.
The Sheriff’s Office Animal Farm features all sorts of animals, both the traditional farm animals like miniature horses, Angus the steer, chickens, pigs, goats, and rabbits, as well as exotic animals like Mo the Sloth, one Kinkajou, Kelsey the Lemur, alpacas (Snowflake, Arabella, Lilo and Stitch), an albino python, peacocks, and many tropical birds.
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Fantasy Fest 2026
Various times and locations
Fantasy Fest is Key West’s legendary 10-day party in paradise — a vibrant celebration of creativity, community, and pure island magic. What began in 1979 as a local idea to liven up the island’s quiet season has transformed into an internationally recognized festival that takes over the streets of Old Town every October.
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Goombay Festival
This event kicks off Key West’s annual premier festival, Fantasy Fest. Goombay is a two-day street party held in Bahama Village. It celebrates the island’s Bahamian roots with nonstop reggae and soca music, Caribbean food, Junkanoo parade dancers, and arts and crafts. The event takes place on Petronia Street, featuring a main stage at Emma Street.
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Zombie Bike Ride
Starts at Fort East Martello Museum, 3501 S. Roosevelt Blvd.
The ride is a little over four miles long and takes a leisurely pace down US1 along the Atlantic Ocean, right at sunset. The Zombie Bike Ride has grown to epic proportions with the help of thousands of fun-loving, bike-riding, costume-sporting, and rock-and-roll townspeople. A police escort leads the ride down US1, past the Zombie Beach Bash at Salute! On The Beach, downtown to Duval Street, where the ZombieFest continues in an epic Street Party of Zombie Bike Ride proportions!
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4:00 PM - 7:00 PM
Locals' Masquerade March
Start Location: Corner of Frances St. and Petronia St.
Join the hugely popular Fantasy Fest tradition, known as The Locals’ Parade, highlighting costumes, creativity, and community. The Masquerade March struts through Old Town and straight into the Fantasy Fest Street Fair, with music, noisemakers, and complimentary drinks along the way.
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6:00 PM - 8:00 PM
Annual Fantasy Fest Parade
The grand finale of the Fantasy Fest celebration. Join the thousands of festival-goers along Duval Street for iconic floats portraying this year’s theme: Musical Icons and Iconic Musicals.
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12:00 PM - 5:00 PM
Children’s Day 2026
Bayview Park, 1320 Truman Ave.
A family event featuring food, rides, games, arts and crafts, and a costume contest for children!
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1:00 PM - 3:00 PM
Monroe County Sheriff’s Animal Farm
5501 College Rd.
The Sheriff’s Office Animal Farm features all sorts of animals, both the traditional farm animals like miniature horses, Angus the steer, chickens, pigs, goats, and rabbits, as well as exotic animals like Mo the Sloth, one Kinkajou, Kelsey the Lemur, alpacas (Snowflake, Arabella, Lilo and Stitch), an albino python, peacocks, and many tropical birds.
