Berryville

Trail Running Calendar near Berryville 2026-2027

Explore the top trail runs near Berryville for 2026-2027! We've gathered 23 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

June 2027

Jun

The More Miles Last One Standing Challenge

Knoxville | 21 mi from Berryville

Backyard Ultra 4 mi

A backyard ultra in Knoxville Maryland where runners repeat a 4.167 mile loop each hour until one remains; includes a 1 mile Mortals edition and prize money.

August 2027

Aug

Third Winchester Battlefield Half

Winchester | 10 mi from Berryville

Trail Run 5 km 10 km Half Marathon

Trail races at Third Winchester Battlefield offering 5k, 10k and half marathon options with a virtual race option and series points.

Aug

Leopold's Preserve 5K & 10K

Broad Run | 26 mi from Berryville

Trail Run 5 km 10 km

A trail run at Leopolds Preserve offering 5k and 10k courses, chip timing, finisher medal and technical shirt, plus water stations and a virtual race option.