Trail Running calendar near Leonardtown 2026-2027

A themed Forrest Gump fun run at Lakeside Loop in New Town Village, Owings Mills, offering a full 4.4-mile loop or a 1-mile out-and-back option. The event is free and participants are encouraged to wear the red hat, yellow top and red short..

A 5 km and 10 km race at Nottoway Park in Vienna, VA on July 11, 2026, described as a scenic route. The event also offers virtual entry options with choices for medals and shirts and uses tiered registration pricing.

Experience the West Side Quarry trail race along the Rappahannock River in Fredericksburg. This 10k course features a steady climb and rolling hills with 426 feet of elevation gain for a dynamic running experience.

A six hour endurance run and a three person relay at Quiet Waters Park in Annapolis. Loops are about 4.25 miles with two aid stations on course, awards by category, and a branded sport duffel premium.

Experience the twisty single track and scenic farm fields of Germantown at this trail running event. Participants can choose between two distances while supporting local non profits in Montgomery County.

A 5K and a half marathon along the Chesapeake & Ohio Canal in Georgetown on July 25, 2026, with in person and virtual options; walkers are welcome and each race has a specific start and finish location.

In-person 5K and 10K at Locust Shade Park in Triangle, VA on July 25, 2026, run on shaded scenic trails. Virtual entries are also available and walkers are welcome.

Trail races at Little Bennett Regional Park on August 1, 2026 feature a 3.7 mile 5K plus and a 6.2 mile 10K on twisty singletrack with hills and streamside sections. Staging is near the Prescott Horse Trailer Area in Clarksburg Maryland.

A half marathon and a 50K on the Dahlgren Railroad Heritage Trail in King George, VA on August 8, 2026. Mostly flat rails to trails courses with time limits, finisher medals, apparel options and postrace food including free MooThru ice crea..

Looped trail ultras at Killen's Pond State Park near Felton, DE with 50 mile, 50 kilometer and 12 hour options on a roughly 3.1 mile mostly dirt loop. The format is self supported with water provided and manual lap timing.

Trail running at Patapsco Pickall Area with 25K and 50K options on rolling single track, river crossings, mandatory out-and-backs, staffed aid stations with real food, and a postrace gathering with food and beer.

A 5K and 10K held at Bull Run Marina in Clifton, VA on August 15, 2026, with in-person and virtual entry options and variable registration fees.

A 7K trail race at the Woodstock Equestrian Center with a hilly course that circles fields and runs through wooded single track, presented as a 1969 throwback with 60s music and period attire encouraged.

Leopold’s Preserve 5k & 10k in Broad Run, VA on August 23, 2026 features 5 km and 10 km distances, welcomes walkers, and offers virtual entry options with medal and shirt choices.

Experience an engaging 8 mile trail race through the winding singletrack of Fredericksburg. Navigate rolling hills and punchy climbs in this focused event supported by the local running community.

Muddy Dash Mechanicsville is a 5K mud run at Budds Creek Motocross Park with obstacles, mud pits and slides plus a festival style after party with music, food and beer. Registration options include standard and VIP packages.

Experience a cross country race through Nottoway Park followed by a community picnic. This event features a three mile course and a kids fun run to celebrate the end of the summer season.

A 5K and 10K held at Fifty-Third Winery & Vineyard in Louisa, Virginia on September 5, 2026 with in-person and virtual options. Proceeds support Hooves & Paws Animal Rescue and its sanctuary work.

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.