Sports and races across the Florida Keys, from Key West, Key Largo and Islamorada and beyond, in date order.
12 upcoming events · Updated September 2026
race · Islamorada
7:45 am
“The 8-mile swim to Alligator Lighthouse is a challenge. It’s not for the faint of heart" How it started When World Renowned Artist, Lighthouse Larry decided to swim, in his native town of…
race · Key West
9 am · Key West High School
Who We Are: Healthy Kids Running Series is a five (5) week running program in the spring and fall for kids Pre-K through 8th grade. Each HKRS Series takes place once a week and offers…
race · Key West
Duval St. Pocket Park; 6:00 PM
On Southernmost Runners club calendar; RunSignup may still show 2025.
race · Key West
Higgs Beach, 1000 Atlantic Blvd; 7:00 AM
Confirmed 2026. No 5K. Half price rises after Sept 6.
race · Key West
Tiki House Key West, 203 Duval St; 6:00 PM
Confirmed 2026. Evening costume run during Fantasy Fest (Oct 16-25).
race · Key West
Higgs Beach, 1000 Atlantic Blvd; 10K 7:30 AM, 5K 8:00 AM
Confirmed 2026.
race · Big Pine Key
Big Pine Community Park, 31009 Atlantis Dr
Confirmed 2026. Packet pickup Nov 20 with Golden Knights parachute team.
race · Key West
Southernmost Point Buoy, 1327 Duval St; 8:00 AM
Confirmed 2026. Double Trot Challenge bundle with Hog Trot.
race · Key West
Hog's Breath Saloon, 400 Front St; 8:00 AM
Confirmed 2026. Free shirt and beer.
race · Key Largo
Jewfish Creek Bridge (18-Mile Stretch); 7:30 AM
Confirmed 2026. 10K nearly sold out as of Sept 6; shirts to first 500.