September
September 1-30
Local’s Month
The entire month of September offers Monroe County locals FREE* admission to Historic Tours of America attractions: Old Town Trolley Tours, Conch Tour Train, Ghosts & Gravestones, Key West Aquarium, Key West Shipwreck Treasure Museum, and Truman Little White House. *Restrictions apply.
September 2-6
Key West WomenFest
Various times and locations
For the women who have felt unseen, unheard, or untethered from their creative selves, this is your invitation. Womenfest returns for five days in paradise, created by women, for women, who are ready to reconnect with their artistry, their stories, and one another.
September 3-7
Just a Few Friends – Margarita Classes at Key West Cooking Show
291 Front St., Ste 207
Dates: September 3, 4, 5, 7. Our 30-minute Turbo-Margarita Class takes you on a journey from the cocktail’s Prohibition beginnings in Mexico to the salt-rimmed anthem of the Conch Republic. Learn the history, hear the Buffett lore, and shake up your own “Real McCoy” Margarita with our expert instructors. 12:00 pm, 2:00 pm, 4:00 pm.
September 3-24
Key West Farmers’ Market
1:00 pm – 6:00 pm
Truman Waterfront Park, at the end of Southard Street
Dates: September 3, 10, 24. Shop local every week with a wide mix of vendors.
September 3-7
Just a Few Friends – Favorite Son Festival
Various times and locations
An annual Labor Day weekend celebration honoring the life, music, and laid-back legacy of Jimmy Buffett. Held in the city that inspired his “Margaritaville” lifestyle, the event features live music, a Second Line walking parade, margarita crawls, and sunset sails.
September 4
Chef’s Encore Dinner Series at Key West Cooking Show
6:00 pm – 8:00 pm
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 The Qin Dynasty. Inspired by the ancient Qin Dynasty and the early roots of Chinese culinary tradition, this supper club experience explores bold flavors, aromatic spices, and time-honored techniques through a contemporary perspective.
September 5
Milagro Margarita March
A curated bar crawl with craft margaritas and a scavenger hunt in the Historic Seaport. Begins at La Concha Key West, 430 Duval St., or The Marker Key West Harbor Resort, 200 William St.
September 5
Key West Brewfest Grand Tasting
Southernmost Beach Resort, 1319 Duval St.
Beer tasting on the beach with live music and poolside events at Southernmost Beach Resort.
September 6
Key West WomenFest Drag Brunch at Key West Cooking Show
12:00 pm – 3:00 pm
Key West Cooking Show, 291 Front St., Ste 207
Enjoy a vibrant afternoon of entertainment, laughter, and a delicious buffet featuring shrimp bisque, French toast with berries, eggs, bacon, sausage, home fries, cured salmon, benedicts, jerk chicken with yellow rice, croissants, fresh fruit, salad, and sweet treats like flan and key lime pie.
September 7-28
Catch the Mania Trivia
6:00 pm – 8:30 pm
Key West Cooking Show, 291 Front St., Ste 207
Dates: September 7, 14, 21, 28. Various themed trivia.
September 13
Monroe County Sheriff’s Animal Farm
1:00 pm – 3:00 pm
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.
September 27
Monroe County Sheriff’s Animal Farm
1:00 pm – 3:00 pm
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.
October
October 1-29
Key West Farmers’ Market
1:00 pm – 6:00 pm
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.
October 2
Chef’s Encore Dinner Series at Key West Cooking Show
6:00 pm – 8:00 pm
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.
October 4
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.
October 5-26
Catch the Mania Trivia
6:00 pm – 8:30 pm
Key West Cooking Show, 291 Front St., Ste 207
Dates: October 5, 12, 19, 26. Various themed trivia.
October 11
Monroe County Sheriff’s Animal Farm
1:00 pm – 3:00 pm
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.
October 16-25
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.
October 16-17
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.
October 18
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!
October 23
Locals’ Masquerade March
4:00 pm – 7:00 pm
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.
October 24
Annual Fantasy Fest Parade
6:00 pm – 8:00 pm
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.
October 25
Children’s Day 2026
12:00 pm – 5:00 pm
Bayview Park, 1320 Truman Ave.
A family event featuring food, rides, games, arts and crafts, and a costume contest for children!
October 25
Monroe County Sheriff’s Animal Farm
1:00 pm – 3:00 pm
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.
November
November 1
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.
November 1-8
Race World Offshore
From thrilling starts to dynamic finishes, the season promises intense competition across diverse waterfront venues. Explore the full schedule and plan your experience.
November 2-30
Catch the Mania Trivia
6:00 pm – 8:30 pm
Key West Cooking Show, 291 Front St.
Dates: November 2, 9, 16, 23, 30. Various themed trivia.
November 5-26
Key West Farmers Market
1:00 pm – 6:00 pm
Truman Waterfront Park, end of Southard St., near 21 E Quay Rd.
Dates: November 5, 12, 19, 26. Shop local every week with a wide mix of vendors.
November 6
Chef’s Encore Dinner Series at Key West Cooking Show
6:00 pm – 8:00 pm
291 Front St.
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 Bella Italia. A celebration of Italian cooking at its most comforting and vibrant, Bella Italia brings together rustic tradition, seasonal ingredients, and bold, satisfying flavors.
November 8
Monroe County Sheriff’s Animal Farm
1:00 pm – 3:00 pm
5501 College Road
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.
November 18-22
Key West Film Festival
205 Whitehead St.
Showcasing films at the Audubon House & Tropical Gardens.
November 22
Monroe County Sheriff’s Animal Farm
1:00 pm – 3:00 pm
5501 College Road
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.
November 26
Thanksgiving Dinner at Key West Cooking Show
11:00 am – 5:00 pm
291 Front St.
Gather your crew and let us take care of the cooking! The Key West Cooking Show is serving a full Thanksgiving dinner buffet at 11 am and 1 pm on this most American holiday. Bar 1 will be open from 11 am – 5 pm, serving drink specials and a traditional plated Thanksgiving meal.
November 26
Lighting of Key West Harbor Walk
631 Greene St.
Annual holiday lighting at the Conch Republic Seafood Company.