Winchester
Trail Running Calendar near Winchester 2026-2027
Explore the top trail runs near Winchester 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.
August 2026
September 2026
A 71 mile clockwise circuit of the orange‑blazed Massanutten Trail around Fort Valley, VA, with multiple aid stations, specific drop bag rules, strict entry qualifications and enforced cutoffs.
The Final Countdown Tribute at Amani Brewing in Martinsburg WV uses a 1.33 mile loop where allowed lap time shortens each circuit, eliminating runners until one remains.
Races at Shenandoah River State Park on September 19, 2026, offering 5k, 10k, half marathon and virtual entry options.
A campus 5K on Sept. 19, 2026 to raise funds for a scholarship supporting students in recovery, with online registration and age-group awards.
A 50K trail race at Sherando Park in Stephens City Virginia on September 19 2026, part of the SPEAR summer trail race series.
A trail run of 9.5 miles at Shenandoah River State Park on September 19, 2026, closing the VHTRC All Access summer series on trail skills with a BBQ finish.
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
For God and Country on 10/03/2026 at John Paul the Great Montessori Academy in Front Royal VA offers 2 mile obstacle and non obstacle trail runs, a 1 mile kids obstacle, and a playground.
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
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.
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.
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.