Trail Running calendar near Leonardtown 2026-2027

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.

Experience a scenic run or walk along the Chesapeake and Ohio Canal path in Georgetown for the Christmas in July 5k and Half. Participants can choose between two race distances or join virtually from any location.

A community trail event on July 25, 2026 at Locust Shade Park in Triangle VA offering 5K and 10K races plus virtual entries with medal or shirt options. Walkers are welcome and entry fees vary by registration period.

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..

An informal, self-supported ultramarathon at Killen's Pond State Park with 50-mile, 50K, and 12-hour options on a shaded 3.1-mile dirt loop, manual lap counting, water provided, and strict storm safety rules.

All trail race at Patapsco Pickall Area offering 25K and 50K on rolling single track with technical sections and river crossings. Aid stations provide water Tailwind and real food and the finish includes shelter food and beer.

Ridge Reaper 5k & 10k takes place on August 15, 2026 at Bull Run Marina in Clifton, VA, using the Bull Run Occoquan Trail. The event offers 5 km and 10 km in-person races plus several virtual entry options with medals and shirts.

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.

A 5K and 10K event at Leopold’s Preserve in Broad Run on August 23, 2026, offering in-person and virtual options and included in the Sippin Series with the Farm Brewery at Broad Run.

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 Maryland is a mud obstacle event at Budds Creek Motocross Park on August 29, 2026 with Value and VIP registration options, on site packet pickup the day before, possible venue parking fees, and free spectator access.

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 road race at Fifty-Third Winery in Louisa, Virginia on September 5, 2026 offering 5K, 10K and several virtual options, with proceeds benefiting 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 24-hour event in Salisbury where individuals and four-person teams run hourly 5K loops on Pemberton Park trails. Points-based scoring, an aid station at start/finish, and awards for top individuals and teams.

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.

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.