Calendar of Events

There's never a dull moment here! View the Key West events calendar!


Key West Food & Wine Festival 2018
Wednesday, January 24, 2018 - Sunday, January 28, 2018 EST


Civil War Days Heritage Festival
Friday, February 02, 2018 8:00 AM - Sunday, February 04, 2018 5:00 PM EST
Fort Zachary Taylor State Park, Key West, FL 33040

The Old Island Days Art Festival
Saturday, February 24, 2018 10:00 AM - Sunday, February 25, 2018 5:00 PM EST
The Old Island Days Art Festival is a two day juried outdoor fine art festival. This nationally recognized show brings over 100 fine artists to this beautiful historic area of Key West. Exhibitors will set up along Whitehead Street from Greene Street to Eaton, and on Caroline Street through the famous Presidential Gates into the beautiful Truman Annex. Set among historical attractions such as Audubon House, the Little White House and Mel Fisher Museum, the City of Key West closes two blocks of Whitehead Street and another block of Caroline Street to vehicle traffic for the show. Visitors can leisurely browse the beautiful displays of paintings from watercolor to oil and acrylic, decorative sculpture, photography and other fine arts from the selected artists. Tropical themes are abundant here, but contemporary and traditional styles make something for everyone!


37th Annual 7 Mile Bridge Run
Saturday, April 14, 2018 6:45 AM - 9:00 AM EST
The 37th Annual 7 Mile Bridge Run will be held on April 14, 2018. Registration will be online only; the registration date will be announced in December. You will have to check back with us then (or follow us on Facebook) to find the exact registration date. Our field of runners fills very quickly - usually in less than 10 minutes. We do not keep lists of interested runners. Hope this information helps!
Additionally, we usually auction several spots. These auctions generally begin in December; people can keep track of this opportunity by following us on FB.

Mote's 2018 Ocean Fest
Saturday, April 14, 2018 10:00 AM - 5:00 PM
Presented by Florida-based Mote Marine Laboratory, the annual event features a kids' fishing seminar, touch tanks and live animals, educational activities, a planned art auction, marine-themed games, refreshments, food and local vendors. The show is set to take place at the Florida Keys Eco-Discovery Center on Truman Waterfront, and celebrates the treasured Keys waters and environment.


23rd Annual Key West Songwriters Festival
Wednesday, May 09, 2018 - Sunday, May 13, 2018 EST
The Key West Songwriters Festival - the largest festival of its kind in the world. Celebrating its 23rd year. Since 1997 BMI has been a presenting sponsor of the festival and has helped it grow into both a tourist attraction and favorite of island locals. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs.


6th Annual Key Lime Pie Festival
Saturday, June 30, 2018 - Wednesday, July 04, 2018 EST
2018 is shaping up to be the best Key Lime Festival yet. We're pleased to offer a full 4 days of culinary events for every taste, including favorites from past years like the Key Lime Cocktail Sip & Stroll, and new favorites for Key Lime lovers like The Key Lime Pie Hop. We've also added intimate culinary events. Once again, we expect most of the events to sell out. Check out our 2018 schedule below. Registration will open soon.


34th Annual Underwater Music Festival
Saturday, July 7, 2018 EST
The nationally-acclaimed submerged songfest is held at Looe Key Reef in the Florida Keys National Marine Sanctuary. The marine musical event is set 10 a.m. to 2 p.m. and staged by Keys radio station US1 Radio 104.1 FM. The music is broadcast underwater via Lubell Laboratory speakers suspended beneath boats positioned above the reef.

26th Annual Hemingway 5K Sunset Run/Walk & Paddleboard Race
Saturday, July 21, 2018 EST
This is the original and oldest ongoing 5K Run in Key West and takes place as part of the annual Hemingway Days Festival. The race course is a scenic flat course that runs past Key West’s most famous landmarks including the Ernest Hemingway Home, the iconic Southernmost Point and the famous Green Parrot Bar.


Ninth Annual Key West Brewfest
Thursday, August 30 – Monday, September 3, 2018 EST
More than 150 beers and micro-brews are on tap at this “tasty” annual event that benefits the charitable efforts of the Key West Sunrise Rotary Club of the Conch Republic. Events from beer dinners, beer brunches, happy hour parties, pool parties, late-night parties, seminars and the Signature Tasting Festival Event are some of the offered activities.

46th Annual Phil Peterson’s Key West Poker Run
Friday September 14, 2018 – Sunday, September 16, 2018 EST
Motorcyclists from throughout the United States are to travel one of America’s most scenic highways to raise money for charity. Riders traverse the Overseas Highway (U.S. Highway 1), the 113-mile roadway from mainland Florida to Key West that features 42 bridges and long vistas of breathtaking open water.


39th Annual Key West Fantasy Fest
Friday, October 19, 2018 – Sunday, October 28, 2018 EST
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.


37th Annual Key West World Championship Races
Sunday, November 4, 2018 – Sunday, November 11, 2018 EST
Super Boat International returns with teams from all around the world who compete April through October in the National Series Points races and conclude in November for the famous Key West World Championships. High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power.