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Join us for the annual holiday lights tour of the island.
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Locals Ride Free*

To take advantage of this offer, signup for your hometown pass.

*Certain restrictions apply. Valid with a resident local ID: Local driver's license or voter's registration.
Sorry, we cannot accept utility bills, rental contracts, etc.

 
October

October 7-8
Southernmost Marathon and Half Marathon Running Festival 10k/5k

This fast and flat course takes you off of the island of Key West, through Stock Island, and up to US 1 for a turnaround. Once back on the island, the Gulf of Mexico greets you to help you finish your race. Multiple races are scheduled over a 2-day weekend.

October 13-16
6th Annual Stand Up Paddle Invitational

Higgs Beach in Key West
Join in the 2 mile paddle board and beach obstacle course. All level of abilities welcome. All events will occur at Higgs Beach in Key West!

October 20-29
38th Annual Fantasy Fest

305-296-1817
This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats. The 2017 festival theme is "Time Travel Unravels."

October 20-22
Bahama Village Goombay Festival - A Family Friendly Event

Corner of Petronia and Fort Street
FREE

This exuberant street party showcases island arts and crafts, music and food in the heart of Key West’s historic Bahama Village neighborhood. The festival’s main entertainment stage is located at the corner of Petronia and Fort Street and features nonstop musical entertainment ranging from gospel to reggae. This family friendly street party continues on Saturday! Noon to midnight.

October 22
Zombie Bike Ride

Fort East Martello Towers
2:00 p.m.

The Zombie Bike Ride Events are set to start at 2:00 p.m. at the Fort East Martello Towers. The closure of the 100, 200 and 300 Block of Duval Street will be from 7:00 p.m. to midnight for this event.

October 27
Smallest Parade in the Universe

5-9PM
Key West Waterfront Brewery

Artists, craftsmen, model makers and creative types are encouraged to participate, making floats no larger than 18 inches! Proceeds benefit the MARC house. Up to $2,000 in prizes.

October 28
Pinup Party

Poolside at 24 North Hotel, 3820 N Roosevelt Blvd.
5:00 pm - 8:00 pm

Join us before the parade craziness for our classic style pinup pool party at one of the largest pools on the island. Wear your vintage swimsuit as you lounge around with a classic cocktail or just float around the pool like a 50's calendar model. Drink specials, party favors, and live entertainment will bring you back to a time when things were a little slower. Pre-game in style!

October 29
Children’s Day

Bayview Park, corner of Truman Ave. and Eisenhower Dr.
Noon to 5 PM
305-292-8912

The premier family event of Fantasy Fest featuring homemade food, rides, games, arts, entertainment and craft booths. A costume contest will be held for children throughout the day. This exciting bash is located at Bayview Park and is sponsored by Old Town Trolley Tours, the Conch Tour Train and First State Bank.

 
November

November 1-5
26th Annual Parrot Heads “Meeting of the Minds”

305-292-1435
The annual event for those interested in the tropical lifestyle and music that Jimmy Buffett personifies. Duval Street will be closed from 8:00 am to 6:00 pm for the Annual Parrot Heads in Paradise Street Party on Friday, November 3, 2017.

November 5-12
37th Annual Key West World Champion Super Boat Races

305-296-6166
Super Boat International returns with teams from all around the world who compete April through October in the National Series Points races and concludes in November for the famous Key West World Championships.

November 11
Annual Veterans Day Parade

4pm
In honor of our Veterans, the annual Key West Veterans Day Parade begins at 4PM at Catherine Street and travels down Duval Street to Front Street.

November 15-19
Key West Film Festival

Now in its 6th year, The Key West Film Festival is an annual celebration of film and filmmakers. Showcased films will represent a broad cross-section of categories that offer a broad set of opportunities for filmmakers, both aspiring and established, to show off what they’ve got.

November 22-26
Sand Isle Professional Sand Sculptures

1500 Reynolds St.
Non-traditional artistry and beachside fun combine in a unique creative experience for participants and spectators. Visitors can watch leading U.S. and international sand sculptors construct and display large-scale creations over Thanksgiving holiday on the Atlantic Ocean beach. Hosted by the Casa Marina, A Waldorf Astoria Resort.

 
December

December 2
Annual Holiday Parade

7-9 pm
Key West will be showing its holiday spirit with the annual hometown parade with marching bands, groups and floats.  Route proceeds down Truman Avenue to Duval, where it takes a right and continues on to Eaton Street. Some streets will be closed for this event.

December 9
Lighted Boat Parade

8 pm
The 27th annual Schooner Wharf Bar & Galley Lighted Boat Parade will festively illuminate the waters at Key West’s Historic Seaport. The vessels will begin parading at 8 p.m. Early arrivers can stroll and enjoy the magical beauty of the Key West Harbor Walk of Lights, then from 6-8 p.m., catch the children's House of Pan Steel Drum Band of Bahama Village as they perform on the Schooner Wharf stage, followed by more live music by Raven Cooper and Friends.

December 31
Dachshund Walk

Noon - 1 pm
Frost-free Key West becomes a "wiener wonderland" when about 200 dachshunds and their owners take a noontime New Year's Eve stroll through the island's picturesque downtown. The "wiener walk" begins at noon Sunday, December 31, at the corner of Whitehead and Fleming streets. The route, deliberately kept brief in deference to the dogs' short legs, is to encompass the 400 block of Fleming Street, 500 block of legendary Duval Street and one-block length of Appelrouth Lane.

December 31
New Year’s Eve Celebration

9 pm
Key West is the best place to be to ring in the New Year with our famous versions of the midnight ball drop. From an over-sized conch shell drop on the rooftop of famous Sloppy Joe's, a pirate wench drop from the mast of a schooner in the Historic Seaport, and the fabulous drag queen Sushi drop from a balcony in a red high heel on Duval Street, you are sure to have a memorable night!

 
For more information: call 1-888-910-8687
 
 
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