Trail Running calendar near Winchester 2026-2027

A 5K running race hosted by Hartwood High School Cross Country on September 12, 2026 in Stafford, VA. It is the first annual StallionsXC Open and serves as the opening race of the Stallion Invitational, with high school races afterward.

A stadium climb at Virginia Credit Union Stadium on September 13 honoring those lost on September 11 and supporting first responders and military. Climbers ascend sections 1 to 23 five times, with a wheelchair accessible concourse route ava..

A 5K cross country festival on September 15, 2026 at Franklin County Fair Grounds, with proceeds benefiting Shalom Christian Academy.

Trail races at Codorus State Park in Hanover, PA offering a 40 Mile Ultra, a 40 Mile Relay, and a 25K plus scenic loops, stocked aid station, camping, and event awards.

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.

Woodstock Warrior is a looped trail event at Seven Bends State Park near Woodstock, VA, with a roughly 10 mile mixed terrain loop and race distances from 10 miles up to 100 miles. It is organized by G.O.A.T. Trail Running.

Trail races at Pine Grove Furnace State Park near Gardners, PA on September 19, 2026 include a 50K, 20 mile, and half marathon across varied single track and ridgelines. Aid stations, limited crew access, drop bag service for the 50K, and r..

Races at Shenandoah River State Park on September 19, 2026 offering a half marathon, 10K, two 5K options and virtual entries with medal and shirt choices.

A campus 5K run/walk on September 19, 2026 in Middletown, VA, with online registration, set fees, age group awards, and proceeds supporting a scholarship and employee wellness initiatives.

Trail races on Cedar Mountain include canicross, a dog friendly 5k, a trail run without dogs, and a virtual option, with awards for top finishers and a traditional hunt breakfast.

SPEAR 50K is a 50 kilometer trail race on September 19, 2026 at Sherando Park in Stephens City, Virginia. It is part of the Sherando Park Endurance Athletic Runners summer trail series and lists details and registration on RunSignUp and Fac..

Two race options on the Chesapeake and Ohio Canal in Georgetown on September 20, 2026, with in person and virtual entries plus medal and shirt choices.

Scenic trail races at Burke Lake Park on September 20, 2026, offering 5k and 10k courses plus virtual options with medals and shirts.

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 and bike events at Sherando Park on September 26, 2026 offering a 4 mile trail race, a one mile untimed fun run, and a 5.3 mile mountain bike time trial. Proceeds benefit the 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.

A 33.3 mile single loop trail run in the George Washington National Forest featuring a climb of Big Schloss with 360 degree views and three aid stations. Entry is limited to 60 runners and opens August 3, 2026.

In-person 5K and half marathon on the Chesapeake & Ohio Canal in Georgetown on September 27, 2026, with virtual options and walkers welcome.

An annual community 5K run and walk at Agricultural History Farm Park in Derwood, Maryland on September 27, 2026, organized by MD District 15 Democratic Caucus. Offers adult and youth entries plus a free youth option with an accompanying ad..

Experience the full reservoir trail system on this thirteen mile course in Fredericksburg. Runners navigate flowing singletrack and five distinct climbs totaling over nine hundred feet of elevation gain through scenic wooded terrain.