Berryville
Trail Running Calendar near Berryville 2026-2027
Explore the top trail runs near Berryville for 2026-2027! We've gathered 25 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
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 5K Saree Run at Oatlands Historic House and Gardens in Leesburg on October 4, 2026 raising breast cancer awareness on a mostly grass, rolling course with wooded trails.
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.
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.
A cross-country 5K and one mile fun run at Ida Lee Park in Leesburg on November 21, 2026, featuring a long sleeve shirt for pre-registered 5K runners and a finisher medal for one mile participants. Donations for Loudoun Hunger Relief are requested.
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 chip timed 5k and 1 miler at Three Fox Vineyard on a gravel and grass loop, with finisher medals, race shirts, live results, 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.
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
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