Berryville
Trail Running Calendar near Berryville 2026-2027
Explore the top trail runs near Berryville for 2026-2027! We've gathered 28 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
September 2026
Cross country at Morven Park with a high school invitational plus an open 5K, featuring food trucks, music and a spectator friendly course.
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.
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
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 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 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.