Winter Haven close

Obstacle Race Calendar near Winter Haven 2025-2026

Explore the top obstacle runs near Winter Haven for 2025-2026! We've gathered 32 exciting races in the area. Check out our detailed list below to find your next local race.

December 2025
Dec
20
Saturday

Santa's Run Fest

5 km 10 km 15 km
Dec
20
Saturday

Santa Hustle Orlando

5 km 10 km
January 2026
Jan
8-10
Th - Sa

Walt Disney World Marathon

10 km
Jan
17
Saturday

Long Haul 100 - Lakeland, FL

Trail Run 13 mi 100 mi
Jan
24
Saturday

Freakin Freezin 5K - Lakeland

5 km
Jan
25
Sunday

Town of Celebration Marathon

21 km 42 km
February 2026
Feb
14
Saturday

Strawberry Distance Challenge

5 km 10 km
Feb
28
Saturday

All Day at Holloway

Trail Run 10 km 30 km 50 km
Feb
28
Saturday

AdventHealth Orange Blossom Half Marathon

5 km 10 km 15 km 21 km
April 2026
Apr
11
Saturday

Colt Creek State Park Trail Run

Trail Run 3 mi 6 mi 13 mi
Apr
18
Saturday

Funest 50K @ Carter Rd

Trail Run 10 km 30 km 50 km
September 2026
Sep
26
Saturday

Margaritaville Run Orlando 10K

5 km 10 km 21 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