Sports & Races in Key West, FL

race

Duval Mile

Duval St. Pocket Park; 6:00 PM

On Southernmost Runners club calendar; RunSignup may still show 2025.

race

Southernmost Half Marathon and 10K (Run Conch Republic)

Higgs Beach, 1000 Atlantic Blvd; 7:00 AM

Confirmed 2026. No 5K. Half price rises after Sept 6.

race

Fantasy Fest 5K Run/Walk

Tiki House Key West, 203 Duval St; 6:00 PM

Confirmed 2026. Evening costume run during Fantasy Fest (Oct 16-25).

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.

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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.

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.

race

Montessori Key West 5K Run/Walk & Kids Fun Run

2025 was Dec 6. Small school fundraiser.

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.

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.

race

Pole Vault in Paradise 2027

8 am

January 7 - 10 2027 Pole Vault Clinic - Friday, January 8, 10 AM to Noon Competition Day - January 9, 2026 On January 5, 2019, the First Annual Pole Vault in Paradise brought together pole vaulters…

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.

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

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…

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Cupid's Chase 5K Key West

Higgs Beach Pavilion, 1000 Atlantic Blvd; 9:00 AM

Confirmed 2027. Price rises after Nov 30, 2026.