Trail Running calendar near Leonardtown 2026-2027

Trials of Miles presents a cross country meet at Morven Park on September 4, 2026, featuring high school competitions and an open 5K for friends and family. The event includes a spectator friendly course with food trucks and music.

The 53rd Winery 5K and 10K on September 5, 2026 takes place at Fifty-Third Winery & Vineyard in Louisa, Virginia. The event includes 5K, 10K and virtual options and benefits Hooves & Paws Animal Rescue.

A 10 mile trail race in Fredericksburg, VA that follows the Rappahannock River, moves through rolling hills, and finishes with a sustained climb. Top three men and top three women receive gift certificates.

Run a scenic off road trail through a 1000 acre farm bordering the Rappahannock River. Enjoy a post race celebration at the brewery with live music craft beer and a souvenir pint glass.

A women only trail event at Fountainhead Regional Park offering a half marathon and a 10k plus on September 12, 2026. Registration runs June 8 to September 1 and two training runs are scheduled in August.

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.

Join the community at Newport News Park for a 5k run across grass, gravel, and paved trails. This accessible local event offers a varied multi surface course through the scenic park grounds.

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 24-hour festival of repeated 5K loops at Pemberton Park in Salisbury, MD, with individual and four-person team divisions, point-based scoring, and required self-support items like a headlamp and personal hydration.

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.

Run the Rock | Rockville is the fourth annual 5K at Luck Stone’s Rockville quarry near Richmond, featuring gravel terrain, quarry views, local food vendors, family activities, swag, and raffles supporting a charitable cause.

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.

AUSA Southern Virginia Chapter hosts a timed 3rd Annual 5K and 10K on the Virginia Capital Trail in Charles City, with race timing, a finisher medal, event SWAG, and proceeds supporting the Charles City High School JROTC Scholarship Fund.

Trail canicross races at Caledon State Park offer two distances, allow leashed dogs, and provide a reusable speedCup; entry fees support Friends of Caledon State Park.

A community charity race in Gaithersburg on October 3, 2026, featuring cross-country 10K and 5K, a paved 1-mile accessible fun run, and a kids Trike-A-Thon. Proceeds support Comfort Cases and Covenant Life School and include a post-race bac..

An endurance event in Prince William Forest Park on October 3, 2026, featuring a 6.5 mile figure eight loop with a 30 km option, a 12 hour format, and a two person relay. The course is fully on trail with two aid stations and limited to 100..

A trail 5K at Claude Moore Park in Sterling, VA on October 3, 2026, featuring forest and leaf-covered paths. The event is the fourth race in the Run Your PRCS Parks series and includes in-person and multiple virtual entry options.

An outdoor adventure race in Midlothian, VA on October 3, 2026 where participants use a map to find 5 to 7 hidden control points and collect tokens. First three finishers with all tokens are champions and a portion of proceeds supports Semp..

Join this annual community trail run through the wooded trail network of Potomac Shores. Residents and guests can choose between 5K and 10K courses for a free morning of outdoor activity in Dumfries.