Nov 04, 2018 - Nov 11, 2018


High-speed offshore powerboats race in Key West Harbor and surrounding waters. Racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power!


Oct 19, 2018 - Oct 20, 2018


This two day festival celebrates Key West’s Bahamian heritage with Island style foods, arts, crafts and a colorful street parade in the heart of Key West’s historic Bahama Village. Enjoy nonstop live music ranging from gospel to reggae, calypso, soca to hip-hop and more. A vibrant family friendly festival free the public.

Oct 19, 2018 - Oct 28, 2018

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.


Oct 21, 2018 - Sunday


Rise from the dead and join your newly awakened zombies as they gather at Zombieland in Fort East Martello at 2 PM to get their blood flowing and bodies painted. Hop on your bike and join the thousands of costumed zombies at 6 PM when the zombie invasion heads down US1 to Duval Street for the Zombiefest in Downtown Key West.


Oct 22, 2018 - Monday

Be super, be evil, be AWESOME and get your run on! Dress up as your favorite Superhero or Super Villain and run, walk or fly to the finish line. Race starts and finishes near the beach at the Southernmost Beach Resort parking lot on South Street, and runs through historic Old Town Key West. Free beer and snacks after the race. Be part of the Fantasy Fest family friendly FUN!


Oct 25, 2018 - Oct 26, 2018

36th Annual Headdress Ball.

Gates Open 6:30 pm. Show begins 8 pm. Key West Amphitheater.

The Key West Business Guild presents the 36 annual Headdress Ball on Thursday, October 25 at 8 pm.

Oct 25, 2018 - Oct 26, 2018

This “over the top” contest includes an extravagant show with lots of Key West razzle dazzle, and is a competition “head and shoulders” above the rest with contestants judged from the shoulders up! Major cash prizes including a $3,000 grand prize. Tickets sell out quickly! Held at the waterside at Truman Waterfront, at the end of Southard Street. Doors open 7 p.m., show begins 8 p.m.

Oct 28, 2018 - Sunday


Children’s day is an annual family event featuring food, rides, games, arts and crafts and an awesome costume contest for children. Located at Bayview Park, Key West. Noon to 5 PM.

305-292-8912 for more info.

Dec 08, 2018 - Dec 16, 2018

Nucracker Key West is dazzling and unique with her tiny chickens, humorous roosters, lively shrimp, and brilliant jewels of the Atocha. A sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City – Key West’s very own NUTCRACKER!

Tennessee Williams Theatre, 5901 College Rd.

Jan 19, 2019 - Jan 21, 2019

The Seafood Festival celebrates our community by bringing families and friends together in a joyful and fun environment to sample the local catch. This family-friendly event was created to showcase local seafood and the Keys’ commercial fishing industry by providing the freshest seafood available. Each year our fishermen and women are proud to offer the community a variety of seafood at reasonable prices along with celebrity chef demonstrations, hands-on eco activities, a boat show and live entertainment all day long.