Trail Running calendar near Leonardtown 2026-2027

Experience a mud run featuring obstacles and trails in King George Virginia. With four mile and one mile options plus team challenges this event supports local community eye and hearing care services.

Night Owl 9K is an evening trail race at Freedom Park in Williamsburg, VA combining single track, fire road and paved trails with rolling hills. The event includes a post race party with beer and pizza and benefits wildlife rehab.

This cross-country event takes place at the Agricultural History Farm Park in Derwood, Maryland. It's part of a free series for members, with paid registration available for non-members and a youth discount.

A free Forrest Gump themed fun run on Lakeside Loop in Owings Mills offering a full 4.4 mile loop or a 1 mile out-and-back option, meeting at New Town Village Center with themed attire suggested.

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.

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.

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.

Experience a scenic out and back race on the mostly flat Dahlgren Railroad Heritage Trail. Choose between a half marathon or 50K distance and enjoy a well supported course featuring finishers medals and cash prizes.

A self-supported ultramarathon at Killen's Pond State Park in Felton, DE offering 50 mile, 50K and a 12 hour option on a mostly dirt 3.1 mile loop. Manual timing, water provided, and hot humid summer conditions.

Trail race in Elkridge, Maryland offering 25K and 50K on rolling single track with river crossings, technical sections and multiple aid stations serving real food, water and Tailwind.

Experience the MCRRC Groovin Woodstock 7K XC at the Woodstock Equestrian Center in Maryland. This low key cross country race offers a scenic 7 km route for club members and non members alike.

Experience the Leopold’s Preserve 5k and 10k in Broad Run Virginia. This Sippin Series event welcomes both runners and walkers for a scenic race through the preserve in collaboration 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.

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.

Test your limits in Kennedyville with the Savage Race or Savage Blitz. Navigate miles of mud and over 25 obstacles to earn exclusive medals and state pins at this premier Maryland event.

Run through the beautiful Fifty-Third Winery & Vineyard in Louisa, Virginia. This 5k and 10k event supports animal rescue and sanctuary efforts for local wildlife and farm animals.

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 at Pemberton Park where individuals or four-person teams run as many hourly 5Ks as they choose, scored by points with overnight bonuses and awards for top individuals and teams.