Big Pine Key close

Trail Running Calendar near Big Pine Key 2025-2026

Explore the top trail runs near Big Pine Key for 2025-2026! We've gathered 16 exciting races in the area. Check out our detailed list below to find your next local race.

October 2025
Oct
20
Monday

Fantasy Fest 5K

5 km
November 2025
Nov
1
Saturday

Zonta ABC Run/Walk

5 km 10 km
Nov
2
Sunday

The Flydog 5K Fun Run/Walk for Pets & Vets Rescue and Transport

5 km
Nov
8
Saturday

Tunnel to Towers 5K - Big Pine Key, FL

5 km
Nov
27
Thursday

Southernmost Turkey Trot 5K

5 km
Nov
29
Saturday

Hog Trot 5K

5 km
December 2025
Dec
7
Sunday

Montessori Key West 5K Run/Walk

5 km
Dec
13
Saturday

A Positive Step of Monroe County

5 km
Dec
14
Sunday

Key West Triathlon

Triathlon
Dec
20
Saturday

Running of the Elves 5K - Key West

5 km
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 Half Marathon
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
Articles
Top 10 Marathons in the Netherlands — The Ultimate Dutch Marathon Bucket List: 10 Unmissable Races
The Beauty of the Easy Run — Why slowing down might be the smartest thing you do for your running
Mizuno Wave Rider 28: Elevating the Legacy of a Running Icon
Garmin Forerunner Review: Garmin Forerunner Series