Winchester
Trail Running Calendar near Winchester 2026-2027
Explore the top trail runs near Winchester for 2026-2027! We've gathered 19 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Community 5K and 1-mile kids run at Clarke County Parks & Recreation with chip timing, course support, awards, and a food drive on November 14, 2026.
A cross country open 5K on a flat course in Purcellville, VA on November 14, 2026, with registration opening November 2 and a $20 fee.
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.
A Thanksgiving Turkey Trot in Martinsburg with a timed 5K, kids races, and donation collection for local backpack programs on the James Rumsey Technical Institute property.
January 2027
Supported point to point mountain run of about 32 miles with roughly 4,600 ft ascent, covering the first third of the MMT 100 course in mid January.
February 2027
A 5k plus adult and kids 1 mile at Three Fox Vineyard with mixed gravel and grass terrain, chip timing, medals, awards, and a virtual race option.
A 30.3 mile training run on Feb 6, 2027 along the middle third of the Massanutten Mountain Trail from Elizabeth Furnace to Camp Roosevelt with two aid stations.
March 2027
A mountainous, very technical 50 km trail run in the Massanutten range with two limited aid stations and about 6,400 feet of elevation change.
April 2027
Trail race at Third Winchester Battlefield on April 4, 2027 offering 5k, 10k and half with chip timing, finisher medal, technical shirt, walkers welcome 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
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.
Trail ultraruns of 100 mile and 100 km on rocky Massanutten Mountain trails near Fort Valley VA, with major elevation gain and a 36 hour cutoff for the 100 mile.
June 2027
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.
A 100 mile loop near Fort Valley, VA, through the Massanutten Mountains with 14 climbs, 14,000 feet of gain, a 24 hour cutoff for the silver buckle, and a 28 hour finish limit.
August 2027
Trail 5k, 10k and half marathon at Third Winchester Battlefield with chip timing, medals, technical shirts, a virtual option and series points.