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Obstacle Race Calendar near The Villages 2025-2026

Explore the top obstacle runs near The Villages for 2025-2026! We've gathered 19 exciting races in the area. Check out our detailed list below to find your next local race.

July 2025
Jul
4
Friday

AdventHealth Clermont Freedom 5K

5 km
Jul
13
Sunday

AdventHealth Cool Sommer Mornings Triathlon

Triathlon
August 2025
Aug
16
Saturday

Hot August Night Trail Race

Trail Run 5 mi 10 mi 20 mi
Aug
16
Saturday

Retro Run

5 km
September 2025
Sep
1
Monday

Labor Day 5k - Ocala

5 km
Sep
14
Sunday

AdventHealth Cool Sommer Mornings Triathlon

Triathlon
Sep
28
Sunday

Pink on Parade 5K

5 km
October 2025
Oct
18
Saturday

Race to Thee, Annabel Lee

5 km
Oct
19
Sunday

Pink Ribbon 5K - Groveland

5 km
Oct
25
Saturday

LSSC Monster Dash

5 km 10 km
November 2025
Nov
8
Saturday

The Florida Run - Lake Louisa State Park

Trail Run 5 km 10 km 13 mi
Nov
27
Thursday

Half Marathon at Baseline Trailhead Park

13 mi
Nov
27
Thursday

YMCA Turkey Trot 10K

5 km 10 km
Nov
27
Thursday

AdventHealth Groveland Turkey Trot 10K

5 km 10 km
December 2025
Dec
13
Saturday

AdventHealth Howey-in-the-Hills Reindeer Dash 5K

5 km
Dec
20-21
Sa - Su

Mount Dora Half Marathon

5 km 13 mi
Dec
20
Saturday

AdventHealth Santa's Twilight 5K

5 km
February 2026
Feb
14
Saturday

Whispering Pines

Backyard Ultra 5 mi
Feb
19-21
Th - Sa

Florida ANVIL Ultra Triathlon

Triathlon
March 2026
Mar
7
Saturday

Shamrock Shuffle - Clermont

5 km 10 km
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