Trail Running calendar near Leonardtown 2026-2027

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.

A road running event on July 11, 2026 at Nottoway Park in Vienna, VA offering 5K and 10K in-person races plus virtual options with tiered registration fees and medal and shirt choices.

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.

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.

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.

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.

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.

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.

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.

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.