Trail Running calendar near Leonardtown 2026-2027

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.

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.

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 mud filled adventure at Budds Creek Motocross Park featuring obstacles and foam pits. Enjoy a community focused event with finisher medals and a post race festival for participants and spectators alike.

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.

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 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.

Join a community 5K run and walk through the scenic trails of Agricultural History Farm Park. Enjoy a morning of music and fitness with events for all ages and awards for top finishers.

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.

Experience a dog friendly trail race through the varied terrain of Caledon State Park. Run a 10K or 1 mile course with your leashed companion to support local natural resources and educational programming.