Berryville
Trail Running Calendar near Berryville 2026-2027
Explore the top trail runs near Berryville for 2026-2027! We've gathered 26 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
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.
Scenic races at Shenandoah River State Park offering a half marathon, 10k and two 5k options with chip timing, finisher medal, technical shirt and a virtual option.
A trail race in Sherando Park listed as the SPEAR summer series 50K, scheduled for September 19, 2026 at the Warrior Drive parking lot in Stephens City VA.
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.
An in-person event on September 26, 2026 in Brunswick, MD featuring a trail-based 5K and timed 3-hour and 6-hour challenges on a 5 mile loop. Proceeds support Brunswick High School Track and Field equipment.
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.
Run On The Rocks in Point Of Rocks, MD on September 26, 2026 features 10 mile, half marathon and 20 mile events. The race is chip timed and includes participant shirts, finisher medals and age group awards.
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 at Oatlands Historic House and Gardens on Oct 4, 2026 supporting Breast Cancer Awareness, with t-shirts, medals, and a mixed grass and trail course.
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 cross country 5K and 1 mile fun run at Ida Lee Park on November 21, 2026, with participant shirts, medals, post-race refreshments, and a food drive for Loudoun Hunger Relief.
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.
February 2027
A chip timed event at Three Fox Vineyard featuring a three-lap 5k, a 1 mile option including a kids race, awards, and a virtual race choice.