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Trail Running Calendar near The Villages 2025-2026

Explore the top trail runs near The Villages for 2025-2026! We've gathered 21 exciting races in the area. Check out our detailed list below to find your next local race.

June 2025
Jun
14
Saturday

The Florida Run Trail Race

Trail Run 4 mi 8 mi
Jun
15
Sunday

AdventHealth Cool Sommer Mornings Triathlon

Triathlon
Jun
21
Saturday

Half Marathon at Baseline Trailhead Park

5 km 10 km 15 km 13 mi
July 2025
Jul
4
Friday

Iggy's Freedom Run

4 mi
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
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