2020 Events & Festivals

Apr 30, 2020 – May 3, 2020
Key West Paddle Classic
Presented by Lazy Dog Adventures, the challenge includes a 12-mile Elite Race around the island and a 4-mile open race. Other events include a kick-off registration party, paddleboard clinics and races for kids.

Jun 2, 2020 – Jun 6, 2020
Fringe Theater presents: Five Lesbians Eating a Quiche
It’s 1956, and the Susan B. Anthony Society for the Sisters of Gertrude Stein are meeting for their annual quiche breakfast. Will they be able to keep their cool when a Communist attack threatens their idyllic way of life? Performance 7 p.m. at Key West Armory, 600 white St. Fringe Theater is Key West’s community-focused theater providing unique opportunities for people to see and do theater.

Jun 3, 2020 – Jun 7, 2020
Key West Pride
Key West shows its Pride every day, and this is your chance to be a part of the celebration! The five-day schedule includes daytime pool and beach parties, late-night drag shows, on-the-water adventures ranging from snorkeling and kayaking to glass-bottom boat tours, a street fair, and pageants to select Mr., Miss and Ms. Key West Pride.

Jun 20, 2020 – Jun 21, 2020
Eighth Annual VFW Fishing Tournament
This is a family friendly event with over $20,000 in cash and prizes. The tournament is both an offshore, and inshore event. Cash prizes for Dolphin,Wahoo,Tuna,Grouper, and Snapper. In addition there are cash prizes for angler categories: Lady Angler, Junior Angler, Pee-Wee Angler, Veteran Angler, Senior Angler, and Active Duty Angler.

Jun 20, 2020
College of the Florida Keys Swim Around Key West
The officially sanctioned event is a 12.5-mile swim clockwise around the island of Key West that is open to all age groups. Individual swimmers and relay teams can compete. The route takes swimmers through the waters of the Atlantic Ocean and Gulf of Mexico, ending where they began at Higgs Beach.

Jun 25, 2020 – Jun 28, 2020
Mango Fest Key West 2020
Mango Fest of Key West features all things mango including mango tasting, mango trees and mango daiquiris. The culinary competitions between local chefs and residents alike showcases the colorful abilities of what the mango, also known as the king of fruit, has to offer. The Vendor Village gives art collectors and foodies the experience of a festival atmosphere. Music is provided along with live radio broadcasts. From 10AM to 3PM, Bayview Park, 1400 Truman Ave.

Jul 2, 2020 – Jul 6, 2020
Eighth Annual Key Lime Festival
A wacky talent show, pie-eating and cooking contests and other tasty temptations await Key West visitors during the annual Key Lime Festival. Four days of culinary events for every taste are planned, 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.

Jul 18, 2020 – Jul 21, 2020
Del Brown Permit Tournament
Anglers fly-fish on the flats in a challenge that honors the late angling pioneer Del Brown, who caught and released more than 500 permit off the Keys. Professionals and guides are allowed to compete as well.

Jul 25, 2020
28th Annual Hemingway 5K Sunset Run/Walk & Paddleboard Race
This is the original and oldest ongoing 5K Run in Key West and takes place as part of the 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. Visit website for more details.

Aug 1, 2020
Slightly Stoopid with special guests Pepper, Common Kings and Don Carlos
Rams Head Key West is thrilled to welcome Slightly Stoopid back to Key West Amphitheater! Enjoy lo-cal food vendors, stocked bars, take home items from local artisans and a one in a million view of The Gulf of Mexico. Come together for a summer night under the stars filled with all of those good vibes served up by four excellent bands. Doors open 4 p.m., show starts 5 p.m. at Key West Amphitheater, 35 E Quay Rd.

Aug 6, 2020 – Aug 9, 2020
24th Annual Key West Lobsterfest: A Crustacean Celebration!
This annual flavorful festival celebrates the Aug. 6 start of the Florida Keys lobster season with a long weekend of tasty events, highlighted by an open-air lobster feast on the island’s famed Duval Street. Events include a Thursday night lobster boil, Friday night Duval Crawl, Saturday street fair with lobster-inspired culinary creations and a free concert, and a luscious lobster brunch Sunday.

Sep 2, 2020 – Sep 6, 2020
Womenfest 2020
Each year thousands of ladies come together over the Labor Day weekend and stay for a wide range of activities and events during four days of revelry and fun. Key West welcomes women from across the globe to an annual celebration that has become one of the largest gatherings of lesbians and friends in North America’s Womenfest.

Sep 3, 2020 – Sep 7, 2020
Key West Brewfest
During a festival “crafted” for Labor Day weekend, attendees can sample nearly 200 beers and ales while also discovering the flavors of the continental United States’ southernmost city. The annual Key West BrewFest is highlighted by a lavish oceanside tasting festival, beer-focused brunches, pool parties featuring specialty beers, daytime tap takeovers and dinners pairing each course with brews that complement the cuisine.

Oct 16, 2020 – Oct 25, 2020
Fantasy Fest
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 2020 festival theme is “Roaring 2020’s & Future Fictions.”

Nov 8, 2020 – Nov 15, 2020
Race World Offshore Key West Championships
High-speed offshore powerboats are to compete in Key West, known internationally as one of the top venues for offshore powerboat racing. Three separate days of racing are scheduled, and the opportunity to for close views of race boats and meeting crew members.

Nov 18, 2020 – Nov 22, 2020
Key West Film Festival
Showcasing films that exhibit excellence in storytelling, the festival’s lineup is to feature screenings and special events hosted at landmark venues throughout Key West, including the San Carlos Institute, Studios of Key West and Key West Theater. The four-day program is to include several films from multiple genres and categories as well as social events with filmmakers, actors and film lovers.