Trail Running calendar near Leonardtown 2026-2027

Test your endurance at this backyard ultra near Loch Lothian in Midlothian VA. Run a 4.167 mile loop every hour until only one participant remains while supporting the Semper Fi Fund and celebrating US history.

Run through history on the secret training trails of the CIA's predecessor in Prince William Forest Park. This night event features a 50-mile, two-loop course with a 14.5-hour limit, or a single 25-mile option. Pacers are allowed for the se..

Combine a 5k run or walk with vineyard scenery at Corteau Vineyards. Registration includes a wine glass, medal, and a wine pour, with age group awards for top finishers. Leashed dogs are welcome on this cross-country style course.

Event Overview The Fauquier Education Farm 5K and Fun Run is a fundraising event for the Fauquier Education Farm, a 501(c)(3) organization. The organization's mission is to advance agriculture through education and best practice farming. It..

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.

Kick off the Blue Crab Bolt series at Seneca Creek State Park with scenic 5K and 10K trail runs featuring lake views and singletrack paths. Enjoy professional race support, post-run breakfast burritos, and a festive atmosphere.

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.

Tackle the flowy and fun trails at Schaeffer Farms in Germantown, Maryland. Choose from a 5K or a 10K++ course featuring single-track, stream crossings, and open fields. Enjoy post-race food, optional medals, and a festive atmosphere.

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.

Run through the wooded singletrack trails and streams of Little Bennett Regional Park in Maryland. Enjoy a community atmosphere with professional timing, post race breakfast burritos, and distances for different experience levels.

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.