Martinsburg
Trail Running Calendar near Martinsburg 2026-2027
Explore the top trail runs near Martinsburg for 2026-2027! We've gathered 18 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A scenic 5K trail run through rolling forest and fall foliage at Cacapon Resort State Park on 10/11/2026.
The Annual Boulder Dash at Pinesburg Quarry in Williamsport, MD on October 17, 2026 offers three distances : 5 miles, 5K and 1 mile, and the quarry will be closed during the event for safety.
November 2026
Trail races in Little Orleans, MD featuring a 50K and 25K on out and back courses with multiple aid stations and official cutoff times.
A fifth annual community race in Berryville, VA with a 5K on park trails and a 1-mile kids run for ages 10 and under, plus timed results, awards and a local food drive.
A Thanksgiving themed 5 km run at Big Cork Vineyards in Rohrersville, Maryland, on November 14, 2026. The event is timed by J3 Timing and includes a t shirt, collapsible wine glass, finisher medal, and a wine pour.
A November event in Brunswick MD with a full marathon, half marathon, and a Veterans Challenge 5K that features towpath running, river crossings, and historic town sections.
Thanksgiving Day event in Stephens City VA featuring a 5K plus kids fun runs and a Tot Trot with set registration windows and no race day registration.
Thanksgiving 5k and kids races at James Rumsey Technical Institute supporting local backpack programs and youth initiatives.
January 2027
5k 10k and half marathon on the flat C&O Canal Trail at Williamsport Park with chip timing, medal, technical shirt and a virtual option.
March 2027
Point of Rocks on March 7, 2027 features a mostly flat gravel out and back with 5k, 10k and half marathon options, limited water stations and a virtual option.
April 2027
Trail 5k, 10k and half marathon at Third Winchester Battlefield with chip timing, finisher medal, technical shirt, series points and a virtual option.
A 100 mile race on the scenic C&O Canal with an almost entirely flat course, starting and finishing at Camp Manidokan near Knoxville, Maryland, Apr 24 and 25 2027.
May 2027
June 2027
A backyard ultra in Knoxville MD where runners repeat a 4.167 mile loop each hour until one remains; a parallel 1 mile Mortals Edition runs under the same rules.
A 46th annual memorial five mile run on the C&O Canal Towpath in Williamsport MD with chip timing, awards, and a technical race shirt.
August 2027
Trail races at Third Winchester Battlefield offering 5k, 10k and half marathon options with a virtual race option and series points.