Berryville
Trail Running Calendar near Berryville 2026-2027
Explore the top trail runs near Berryville 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.
November 2026
A trail 5K at Cacapon Resort State Park on November 1, 2026, over forest single-track and gentle hills, with a $35 fee and medals for the first 122 registrants.
Community 5K and 1-mile kids run at Clarke County Parks & Recreation with chip timing, course support, awards, a food drive, and door prizes.
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 on mixed gravel and grass plus a one mile loop at Three Fox Vineyard, with medals, age group awards, and a virtual option.
A 30.3 mile training run along the middle third of the MMT from Signal Knob to Camp Roosevelt with two aid stations and limited entry.
March 2027
A chip-timed 5 km, 10 km and half marathon at Point of Rocks on March 7, 2027 with limited water stations, a virtual option, and finisher medals and shirts.
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
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.