Sports & Races in Key West, FL
Sports and races within 15 miles of Key West — in date order.
17 upcoming events · Updated October 2026
Saturday, Oct 240 events
1 event
race
Zonta ABC (Awareness Breast Cancer) Run/Walk (34th annual)
Higgs Beach, 1000 Atlantic Blvd; 10K 7:30 AM, 5K 8:00 AM
Confirmed 2026.
0 events
race · Big Pine Key · 28 mi
Tunnel to Towers 5K Run & Walk - Big Pine Key
Big Pine Community Park, 31009 Atlantis Dr
1 event
race
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
1 event
race
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
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.
1 event
race
Montessori Key West 5K Run/Walk & Kids Fun Run
2025 was Dec 6. Small school fundraiser.
Expected · confirm date
1 event
race
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
1 event
race
Rudolph Red Nose Run (A Positive Step of Monroe County 5K, 18th annual)
Southernmost Beach Cafe, 1405 Duval St; 8:00 AM
Confirmed 2026. Holiday-pajama theme.
1 event
race
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
race
34th Annual ABC Run/Walk
7:30 am · Key West
Participate in the annual ABC Run/Walk supporting local charities.
2 events
race
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 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 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
1 event
race
Cupid's Chase 5K Key West
Higgs Beach Pavilion, 1000 Atlantic Blvd; 9:00 AM
Confirmed 2027. Price rises after Nov 30, 2026.
0 events
race · Big Pine Key · 28 mi
Run With Deer 5K Run/Walk (11th annual)
Big Pine Community Park, 31009 Atlantis Dr; 8:00 AM
Expected · confirm date
1 event
race
Irish Kevin's Shamrock Shuffle 1K/5K/10K 2027
8 am
RUN. WALK. SHUFFLE. CELEBARTE! Get ready to celebrate St. Paddy's at the 14th annual Irish Kevin's Shamrock Shuffle! Run, walk, or shuffle your way through Key West, then head back to Irish Kevin's…
$20