Trail Running calendar near Leonardtown 2026-2027

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.

Muddy Dash Mechanicsville is a 5K mud run at Budds Creek Motocross Park with obstacles, mud pits and slides plus a festival style after party with music, food and beer. Registration options include standard and VIP packages.

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 community road race on September 5, 2026 at Fifty-Third Winery & Vineyard in Louisa, VA offering 5 km and 10 km courses plus virtual options. Proceeds support Hooves & Paws Animal Rescue, a nonprofit sanctuary and adoption organization.

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 in Salisbury, MD where individuals and four person teams run repeated 5K loops. Scoring is point based with bonuses for night runs, placing points, and awards for top individuals and teams.

A quarry-based 5K at Luck Stone Rockville on September 26, 2026, featuring gravel terrain, quarry views, vendors, family activities, and raffles. Registration opens May 21 with a $25 fee.

An annual community 5K run and walk at Agricultural History Farm Park in Derwood, Maryland on September 27, 2026, organized by MD District 15 Democratic Caucus. Offers adult and youth entries plus a free youth option with an accompanying ad..

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.

Trail canicross races at Caledon State Park offer two distances, allow leashed dogs, and provide a reusable speedCup; entry fees support Friends of Caledon State Park.

A 12 hour trail run at Prince William Forest Park featuring a 6.5 mile figure eight loop on single track and fire road, two aid stations, and options for solo or two person relay teams.

A trail 5K at Claude Moore Park in Sterling, VA on October 3, 2026. Part of the Run Your PRCS Parks timed series, it offers in-person and several virtual entry options with medal and shirt choices.

Experience the scenic beauty of Pocahontas State Park at this trail festival featuring a loop course 10k and half marathon. Enjoy runnable trails and professional timing in a picturesque Virginia forest setting.

Trail races at the Workhouse Arts Center in Lorton VA on October 4, 2026. Options of 5.4 or 10 miles on mostly singletrack through forest and meadow across the former prison grounds.

A trail event at Pohick Bay Regional Park in Lorton, VA on October 4, 2026 offering 5K and 10K distances plus several virtual entry options; walkers are welcome and registration fees vary by date and option.

A Halloween themed 4 mile trail run and hike at York River State Park on a new course that includes dirt trails, rolling hills, single track and riverside views. The format is non competitive with finisher medals and post race refreshments.

A trail-based community event on October 11, 2026 at Bretton Woods Recreation Center featuring a 5K run and 1 mile walk to support the Michael Long Memorial Fund and addiction prevention and recovery services.

A natural-surface 10K at Black Hill Regional Park with rocky, root-strewn trails and varied terrain. Part of MCRRC's low-key series with free entry for members and paid registration for non-members.