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Running Calendar near Big Pine Key 2025-2026

Explore the top running races near Big Pine Key for 2025-2026! We've gathered 12 exciting races in the area. Check out our detailed list below to find your next local race.

August 2025
Aug
30
Saturday

Parrots and Margaritas 5K

5 km
October 2025
Oct
12
Sunday

Southernmost Half Marathon

6 mi 13 mi
November 2025
Nov
1
Saturday

Runway 5K - Summerland Key

5 km
Nov
8
Saturday

Tunnel to Towers 5K - Big Pine Key, FL

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
10
Saturday

Save Our First Responders 5K

5 km
Jan
17
Saturday

Key West Half Marathon

5 km 8 km 10 km 21 km
February 2026
Feb
14
Saturday

Cupid's Chase Key West 5K

5 km
Feb
14
Saturday

Run With Deer 5K

5 km
May 2026
May
16-17
Sa - Su

KEYS100 Ultramarathon

50 km 50 mi 100 mi
July 2026
Jul
25-26
Sa - Su

Hemingway Sunset Run 5K

5 km
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