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Trail Running Calendar near The Villages 2026-2027

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Explore the top trail runs near The Villages for 2026-2027! We've gathered 16 exciting races in the area. Check out our detailed list below to find your next local race.

Trail Running Calendar United States
September 2026
Sep
12
Sa

Back-to-School Bash - Eustis

Trail Run 2 mi 3 mi
October 2026
Oct
17
Sa

The Itch - Ocala, FL

Trail Run 50 km
Oct
24
Sa

PawPals 4 Life 5k

Trail Run 5 km
Oct
24
Sa

Greenway Trick 'R Trot

Trail Run 5 km 10 km 15 km
Oct
25
Su

Clermont Clay 15K

Trail Run 5 km 15 km
Monthly updates for The Villages

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Oct
31
Sa

Nightmare on the Clermont Trails 5K

Trail Run 5 km
November 2026
Nov
7
Sa

Lake Louisa State Park Trail Run

Trail Run 5 km 10 km Half Marathon
Nov
14
Sa

Landbridge Trail 5K

Trail Run 5 km
Nov
26
Th

Turkey Day 5K Clermont

Trail Run 5 km
Nov
28
Sa

Turkey Burn Ultra

Trail Run 25 km 50 km
February 2027
Feb
14
Su

Run for the Woods - Sorrento

Trail Run 3 mi 7 mi 13 mi
Feb
27
Sa

Marion County Run for the Springs

Road Race Trail Run 5 km
Feb
27
Sa

Painted Horse Urban Ultra

Trail Run 25 km 55 km
March 2027
Mar
28
Su

Silver Springs Half Marathon

Trail Run 3 mi 6 mi 13 mi
April 2027
Apr
24
Sa

Skunk Ape 100 Mile Endurance Run

Trail Run 50 mi 100 mi
May 2027
May
23
Su

Sweat, Swat ‘n Swear

Trail Run 10 mi 25 km 50 km
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