Trail Running calendar near Leonardtown 2026-2027

A Backyard Ultra in Midlothian on June 13 and 14, 2026, with repeating 4.167 mile loops every hour. Proceeds support the Semper Fi Fund; the last runner standing wins cash and the Sword of Honor.

Celebrate Juneteenth with a scenic trail run through the hilly terrain of Schaeffer Farm in Germantown. Choose between 6k and 12k distances on a course that welcomes both runners and walkers.

Experience a scenic run or walk along the Chesapeake and Ohio Canal path in the heart of Georgetown. Choose between a 5k or 10k course located right near the nations capital.

A trail running event at Seneca Creek State Park on June 27, 2026, offering measured 5K and 10K courses through singletrack with lake views, aid stations, post-race food, and age division awards.

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.

Experience the Night Owl 9K at Freedom Park featuring technical single track trails and rolling hills. Enjoy a post race party with pizza and live owls while supporting local wildlife rehabilitation.

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.

The MD Heat Trail Race on August 15, 2026, offers 50K and 25K trails with river crossings and valley views. Finish with a celebration featuring craft beer and BBQ.

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.