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Trail Running Calendar near Winchester 2024-2025

Explore the top trail runs near Winchester for 2024-2025! We've gathered 6 exciting races in the area. Check out our detailed list below to find your next local race.

January 2025
Jan
18
Saturday

Twisted Oak 8k

Trail Run 8 km
February 2025
Feb
15
Saturday

Trail Demon 10k

Trail Run 10 km
April 2025
Apr
26
Saturday

C&O Canal 100

Trail Run 100 mi
Apr
26
Saturday

Winchester Battlefield Half

Trail Run 5 km 10 km 13 mi
May 2025
May
4
Sunday

The Four Leaf Clover Project's Run for Prosperity

Trail Run 5 km
May
17
Saturday

Massanutten Mountain Trails 100 Mile Run

Trail Run 100 mi
May
31
Saturday

Barrel Oak 6k

Trail Run 6 km
June 2025
Jun
7
Saturday

One Family Brewing 5k

Trail Run 5 km
Jun
7
Saturday

Old Dominion

Trail Run 100 mi
Jun
8
Sunday

Crooked Run Valley 10k

Trail Run 10 km
July 2025
Jul
26
Saturday

868 Estate Vineyards 10k

Trail Run 10 km
August 2025
Aug
9
Saturday

Third Winchester Battlefield Half

Trail Run 5 km 10 km 13 mi
September 2025
Sep
6
Saturday

The Inferno 10k

Trail Run 10 km
Sep
14
Sunday

Valley View Hard Cider Challenge Half

Trail Run 13 mi
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