Sports & Races in the Florida Keys
Sports and races across the Florida Keys, from Key West, Islamorada and Big Pine Key and beyond, in date order.
22 upcoming events · Updated October 2026
Saturday, Oct 241 event
1 event
race · Key West
Zonta ABC (Awareness Breast Cancer) Run/Walk (34th annual)
Higgs Beach, 1000 Atlantic Blvd; 10K 7:30 AM, 5K 8:00 AM
Confirmed 2026.
1 event
race · Big Pine Key
Tunnel to Towers 5K Run & Walk - Big Pine Key
Big Pine Community Park, 31009 Atlantis Dr
Confirmed 2026. Packet pickup Nov 20 with Golden Knights parachute team.
1 event
race · Key West
Key West Half
7 am
Most finish lines give you a medal. This one gives you a story. It starts in Key West, where the ocean frames the course, the island wakes up around you, and the road ahead feels like an invitation…
$55
2 events
race · Key West
Southernmost Turkey Trot 5K & 1-Mile Rooster Romp (4th annual)
Southernmost Point Buoy, 1327 Duval St; 8:00 AM
Confirmed 2026. Double Trot Challenge bundle with Hog Trot.
1 event
race · Key West
Hog Trot 5K (Hog's Breath Saloon, 32nd annual)
Hog's Breath Saloon, 400 Front St; 8:00 AM
Confirmed 2026. Free shirt and beer.
3 events
race · Key Largo
First State Bank Key Largo Bridge Run (15th annual)
Jewfish Creek Bridge (18-Mile Stretch); 7:30 AM
Confirmed 2026. 10K nearly sold out as of Sept 6; shirts to first 500.
1 event
race · Key West
Montessori Key West 5K Run/Walk & Kids Fun Run
8 am · Truman Waterfront Park
Caring for our bodies is as important as caring for our minds. Join us the morning of Sunday, December 6th as we throw a celebration of fitness and community and raise crucial funding for our dreamy…
$20
2 events
race · Islamorada
Islamorada Half Marathon & 10K + Rumrunner Run 5K/10K (12th annual)
Overseas Hwy, Islamorada
Confirmed 2026. Largest Upper Keys race weekend. Info: islamoradarunning.com
race · Key West
Rudolph Red Nose Run (A Positive Step of Monroe County 5K, 18th annual)
Southernmost Beach Cafe, 1405 Duval St; 8:00 AM
1 event
race · Islamorada
Islamorada Half Marathon & 10k, Rumrunner Run 5K/10K and Beach N' Beer Mile
7 am · Overseas Hwy
Welcome to the 12th annual Islamorada Half Marathon & 10K, Rumrunner Run 5K and Beach N’ Beer Mile! Our full weekend of road races and parties has become a bucket list event for people from all over…
$80
1 event
race · Key West
Running of the Elves 5K & Jingle Bell Mile
Start at Lobster Trap Christmas Tree (Margaret St); finish at Dante's, 951 Caroline St; 6:00 PM
2026 date per event listings; RunSignup page not yet rolled over from 2025. Verify.
2 events
2 events
race · Key West
Save Our First Responders 5K (2nd annual)
Truman Waterfront Park (3 laps); 8:00 AM
Confirmed 2027. Packet pickup Jan 8 at Fit2Run, 211 Duval.
1 event
race · Key West
Key West Half Marathon & Runfest (29th annual)
5K/10K: Higgs Beach, 1000 Atlantic Blvd. Half/8K: Caroline St & Trumbo Rd, finish behind Waterfront Brewery. Expo: Half Shell Raw Bar
Confirmed 2027. Price increase after Sept 30, 2026. Multi-race challenge bundles available. Info: keywesthalfmarathon.com
2 events
race · Key West
Key West Half Marathon & 5K, 8K, 10K, Rum Stroll & Beer Mile
7 am
KEY WEST HALF MARATHON VOTED ONE OF THE 10 BEST HALF-MARATHONS ACROSS THE NATION FOR 2023 IN USA TODAY!!! CLICK HERE TO LEARN MORE! Welcome to our 29th Year! The 29th Annual Key West Half Marathon…
$59
Nothing else in The Florida Keys