Trail Running calendar near Leonardtown 2026-2027

Experience one of the oldest 50 mile trail races in the country through the forested rolling terrain of Virginia. This spring event features a historic course through bluebells with a generous 13 hour time limit.

Run a scenic 5k cross-country course at a Virginia vineyard. The event welcomes runners and walkers alike and offers virtual participation options. It takes place in Warrenton on April 4, 2026.

Experience a unique 14 mile point to point trail run through the forests of Virginia. Enjoy a flat course featuring themed aid stations serving pie and s'mores while supporting local children's charities.

Experience a scenic trail run at Pohick Bay Regional Park featuring waterfront views and historic surroundings. Choose between 5.9 and 10.4 mile courses through single track trails with professional support and activities for the whole fami..

Experience a fast and flat race along the scenic Chesapeake and Ohio Canal Towpath in Potomac. With 5k, 10k, and half marathon distances available, walkers and runners are invited to set new personal records at Carderock Park.

A looped trail event at Piney Run Park offering 50K, 25K, a 5.25 mile race, and an 8 hour challenge, with aid stations, race amenities, packet pickup, and proceeds supporting the club, youth programs, a scholarship, and cancer research.

Join the Sip & Stride 5k and 10k in Louisa Virginia for a chance to earn points in the Sippin’ Series. Choose between in person racing or multiple virtual participation options with medals and shirts.

Experience a trail run through Lake Fairfax Park in Reston featuring scenic lake views and smooth singletrack paths. Choose between 5.3 and 10.3 mile distances on a course with frequent short hills and minimal pavement.

Experience a unique trail race through an active rock quarry at the Luck Stone Leesburg Plant. This 5K event supports environmental preservation and features family activities and awards for all ages.

An annual 5K at Marymount University on April 25, 2026, run on the Bluemont and Custis Trails with a post-race gathering, a virtual option, chip timing, and guaranteed shirts for early registrants.

A multi-distance trail event at Agricultural History Farm Park featuring a 5-mile loop used for timed 3-, 6-, and 10-hour challenges plus a traditional marathon and 25K, with rolling hills and a well-stocked aid station.

Join the inaugural Run Rock Creek 5K/10K in Washington D.C. to experience a forest run through America’s premier urban national park while supporting vital trail restoration and conservation efforts.

Participate in a scenic trail run in Lorton to support Gunston Elementary School. This community event features 10K, 5K, and Fun Run distances with proceeds funding student enrichment and arts programs.

Trail half marathon and 10K at Fountainhead Regional Park near Washington D.C. Courses feature singletrack with rocks and roots, stream crossings, multiple aid stations, and notable climbs, with chip timing and postrace support.

Join the 10th annual cross country event at Spencerville Adventist Academy featuring a 5K, 1 Mile run, and Kids Fun Run. Enjoy a campus course with finisher medals, team options, and a costume contest for all participants.

The Johnnycake Jolt Series is a four-week trail run event on Wednesday evenings in May. Runners can tackle a scenic 10 km course in the Pickall Area of Patapsco Valley State Park. It’s a grassroots series designed to bring the local running..

Experience a premier obstacle course and mud run in Kennedyville, Maryland. Choose between the 5-7 mile Savage Race or the 3+ mile Blitz featuring over 25 unique obstacles and earn exclusive Syndicate medals.

Experience the beauty of the Gunpowder Watershed in Parkville Maryland with a choice of trail distances. Support local land conservation while enjoying single track trails and family friendly activities.

The Johnnycake Jolt Series offers four weekly 10k trail runs in Patapsco Valley State Park. It's a grassroots, low-key event organized by park stewards, with a discount for park members.

Event Overview The Trail Running Events at Dominion Energy Riverrock is a series of trail races taking place over three days in May. All events start and finish at the Belle Isle Parking Lot in Richmond, Virginia. The Races Three separate t..