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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 10 exciting races in the area. Check out our detailed list below to find your next local race.

February 2025
Feb
8
Saturday

Cupid's Chase Key West 5K

5 km
Feb
15
Saturday

Run With Deer 5K

5 km
March 2025
Mar
15
Saturday

Irish Kevin's Shamrock Shuffle 10K

5 km 10 km
Mar
15
Saturday

Time to Paddy Half Marathon - Key West

5 km 10 km 13 mi
Mar
29
Saturday

Sugarloaf School PTO Fins Up 5K Run/Walk

5 km
April 2025
Apr
19
Saturday

Earth Day Run

5 km
May 2025
May
17-18
Sa - Su

KEYS100 Ultramarathon

50 km 50 mi 100 mi
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
14
Sunday

Key West Triathlon

Triathlon
January 2026
Jan
17-18
Sa - Su

Key West Half Marathon

5 km 8 km 10 km 13 mi
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