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Trail Running Calendar near Windermere 2026-2027

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Explore the top trail runs near Windermere for 2026-2027! We've gathered 17 exciting races in the area. Check out our detailed list below to find your next local race.

September 2026
Sep
12
Sa

Back-to-School Bash - Eustis

Trail Run 2 mi 3 mi
Sep
27
Su

Bodies Race Company - Orlando

Trail Run 3 mi 6 mi 13 mi
October 2026
Oct
10
Sa

We Care 5K

Trail Run 5 km
Oct
24
Sa

PawPals 4 Life 5k

Trail Run 5 km
Oct
25
Su

Clermont Clay 15K

Trail Run 5 km 15 km
Monthly updates for Windermere

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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
7
Sa

Bodies Race Company - Orlando

Trail Run 3 mi 6 mi 13 mi
Nov
26
Th

Turkey Day 5K Clermont

Trail Run 5 km
Nov
28
Sa

Turkey Burn Ultra

Trail Run 25 km 50 km
December 2026
Dec
13
Su

Bodies Race Company - Orlando

Trail Run 3 mi 6 mi 7 mi
January 2027
Jan
23
Sa

Monroe Cross Trail 50 Mile Ultra

Trail Run 17 km 50 km 50 mi
February 2027
Feb
13
Sa

Lake Apopka Scenic Trail

Trail Run 5 km 8 mi 13 mi 30 km
Feb
14
Su

Run for the Woods - Sorrento

Trail Run 3 mi 7 mi 13 mi
March 2027
Mar
14
Su

Formosa Spiked Apple 5K

Trail Run 5 km
May 2027
May
8
Sa

Run for the Trees Jeannette Genius McKean Memorial 5K

Road Race Trail Run 5 km
June 2027
Jun
26-27
Sa - Su

Independence Double

Urban Trail 5 km 10 km ... 26 mi 50 km
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