Winchester
Trail Running Calendar near Winchester 2026-2027
Explore the top trail runs near Winchester 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.
September 2026
Trail event at Sherando Park in Stephens City, VA offering a timed 4-mile mixed-surface race and an untimed 1-mile out-and-back on the paved path, supporting I'm Just Me Movement.
October 2026
A community day at John Paul the Great Montessori Academy featuring a 2 mile obstacle trail run, a 2 mile no obstacles run, a 1 mile kids obstacle and family activities.
A scenic 5K trail run through rolling forest, single-track and gentle hills at Cacapon Resort State Park in Berkeley Springs, WV on October 11, 2026.
Evenstar Ultras is a timed trail event at Shenandoah River State Park with 3, 6, 12 and 24 hour options on a 3.48 mile loop. Frequent returns to the main aid station reduce the need to carry heavy gear.
November 2026
A 5K and a 1 mile kids fun run at Clarke County Parks and Rec in Berryville on November 14, featuring trail and roadway courses, awards, chip timing and a food drive.
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
A supported point to point mountain training run of 32 miles that follows much of the first third of the MMT 100, with two aid stations, required car shuttle, limited club support, and recommended GPX and turnsheet navigation.
February 2027
A winery event on February 6, 2027 featuring a three-lap 5K over gravel, grass and hills, plus adult and kids 1 mile options with medals and awards.
March 2027
The Elizabeth Furnace 50 km is a technical mountain trail race in the Massanutten range covering 30.5 miles and about 6,400 feet of ascent. Aid is limited with staffed stations near 10 and 22 miles so runners must carry personal supplies.
April 2027
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
Shenandoah Sky in Bentonville, Virginia on May 15, 2027 offers a Mountain 25K with 1700+ feet of climbing, an 8 Mile trail race, and an untimed 8 Mile hike through river, valley, and forest single track.
Massanutten Mountain Trails 100 is a 100 mile trail ultramarathon in Virginia’s Massanutten Mountains with over 18,000 ft of ascent and a 36 hour cutoff.
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.