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Trail Running Calendar near Winter Park 2026-2027

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Explore the top trail runs near Winter Park for 2026-2027! We've gathered 16 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
October 2026
Oct
24
Sa

PawPals 4 Life 5k

Trail Run 5 km
Oct
25
Su

Clermont Clay 15K

Trail Run 5 km 15 km
Oct
31
Sa

Nightmare on the Clermont Trails 5K

Trail Run 5 km
November 2026
Nov
22
Su

The Great Turkey Trot 5K - Clermont

Trail Run 5 km
Monthly updates for Winter Park

Get new running races (and updates) in your inbox every month.
Nov
26
Th

Turkey Day 5K Clermont

Trail Run 5 km
Nov
28
Sa

Turkey Burn Ultra

Trail Run 25 km 50 km
January 2027
Jan
16
Sa

Outlast Orlando

Trail Run Backyard Ultra 18 mi
Jan
23
Sa

Monroe Cross Trail 50 Mile Ultra

Trail Run 17 km 50 km 50 mi
Jan
30-31
Sa - Su

Forgotten Florida

Trail Run 8 mi 15 mi 50 mi 100 mi
February 2027
Feb
13
Sa

Lake Apopka Scenic Trail

Trail Run 3 mi 8 mi 13 mi 30 km
Feb
14
Su

Run for the Woods - Sorrento

Trail Run 3 mi 7 mi 13 mi
Feb
14
Su

For the Love of Chocolate 5K

Trail Run 5 km
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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