Winter Haven close

Trail Running Calendar near Winter Haven 2025-2026

Monthly updates for Winter Haven

Get new running races (and updates) in your inbox every month.

Explore the top trail runs near Winter Haven for 2025-2026! We've gathered 11 exciting races in the area. Check out our detailed list below to find your next local race.

December 2025
Dec
20
Sa

Peace River 100 Miler

Trail Run 10 mi 100 mi
January 2026
Jan
17
Sa

Long Haul 100 - Lakeland, FL

Trail Run 13 mi 100 mi
February 2026
Feb
7
Sa

Nighthawk Trail Run - Coyote 10K

Trail Run 5 km 10 km 15 km
Feb
7
Sa

The Hunt for Sasquatch

Trail Run 5 km 10 km 15 km
Feb
15
Su

Longleaf Blaze Trail Run

Trail Run 5 km 10 km
Feb
22
Su

Swan's Song Urban Run

Trail Run 30 km
Feb
28
Sa

All Day at Holloway

Trail Run 10 km 30 km 50 km
March 2026
Mar
15
Su

Formosa Spiked Apple 5K

Trail Run 2 mi 5 km
April 2026
Apr
11
Sa

The Florida Run - Colt Creek State Park

Trail Run 5 km 10 km Half Marathon
Apr
18
Sa

Funest 50K @ Carter Rd

Trail Run 10 km 30 km 50 km
November 2026
Nov
21
Sa

Colt 45 Trail Run

Trail Run 14 mi 45 km 45 mi 60 mi