Oct 07, 2016 - Oct 09, 2016

Presented by Pat Croce’s Rum Barrel, this event is one of a kind! Imagine running through the southernmost island in the United States while enjoying a break from the ordinary. The Southernmost Marathon & Half promises just that- 26.2 or 13.1 miles of ocean and gulf views, as well as iconic Key West landmarks. A full weekend of events include the race and a Sunday Paddle Board race for the Special Olympics of Monroe County.

More info at somomarathon.com

Contact: 305-766-5284

Email: liz@somomarathon.com

Oct 21, 2016 - Oct 22, 2016

Held in Key West’s historic Bahama Village neighborhood, the lively Goombay is known for its island-style food, arts and crafts, nonstop live entertainment and dancing in the streets. Visitors can experience sights, sounds and flavors recalling Key West?s Bahamian heritage.

Oct 26, 2016 - Wednesday

The wacky costume contest for domestic pets and their people is a highlight of the island city’s 10-day Fantasy Fest costuming and masking festival. A magical carousel of frisky pets and playful owners delightfully disguised get ready to frolic for fame and fortune. FREE to watch; fee to enter; benefits Lower Keys Friends of Animals; located at the Casa Marina Resort, 1500 Reynolds St. Starts 5:30 p.m.

Email: petmasquerade@hotmail.com

Oct 27, 2016 - Thursday

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, 2016 - Friday

Thousands of masked and costumed partiers are to unleash their intergalactic alter egos during the free-spirited Fantasy Fest Masquerade March, a lively walking parade through Key West’s historic Old Town. The masquerade march typically attracts spirited bands and merrymakers wearing everything from feathered masks and finery to offbeat costumes inspired by the festival theme. Free to enter and watch, the 2015 promenade is to start at 5 p.m. at the Key West Cemetery’s Frances Street entrance. Participants are to proceed along two routes, stopping for libations at bed-and-breakfast inns along the way.

Oct 29, 2016 - Saturday

Join 70,000 exuberant partygoers as this year’s 3Wishes.com Fantasy Fest parade rolls down Duval Street. Featuring glittering floats, spectacular costumes, and dazzling dancing groups, it doesn’t get any wilder than this! Parade steps off at 7 PM; fantasyfest.com

Oct 30, 2016 - Sunday

A family event featuring food, rides, games, arts and crafts and a costume contest for children located at Bayview Park. Truman Ave. and Eisenhower Dr.; Noon to 5 PM; 305-292-8912.

Nov 06, 2016 - Nov 13, 2016

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.

Contact: 305-296-6166

Email: superboatracing@gmail.com

Nov 23, 2016 - Nov 27, 2016

Nontraditional 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 weekend on the Atlantic Ocean beach at the Casa Marina Resort, 1500 Reynolds St.

Email: info@sandisle.com