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Running Calendar near Key West 2025-2026

Explore the top running races near Key West for 2025-2026! We've gathered 8 exciting races in the area. Check out our detailed list below to find your next local race.

June 2025
Jun
28
Saturday

The Big Gay 5K

5 km
July 2025
Jul
26-27
Sa - Su

Hemingway Sunset Run 5K

5 km
October 2025
Oct
12
Sunday

Southernmost Half Marathon

10 km 13 mi
November 2025
Nov
1
Saturday

Runway 5K - Summerland Key

5 km
December 2025
Dec
13
Saturday

A Positive Step of Monroe County

5 km
Dec
14
Sunday

Key West Triathlon

Triathlon
January 2026
Jan
16-18
Fr - Su

Key West Half Marathon

5 km 8 km 10 km 13 mi
February 2026
Feb
14
Saturday

Cupid's Chase Key West 5K

5 km
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