Trail Running calendar near Leonardtown 2026-2027

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.

A 7K trail race at the Woodstock Equestrian Center with a hilly course that circles fields and runs through wooded single track, presented as a 1969 throwback with 60s music and period attire encouraged.

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 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.

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.

Run the Rock Rockville is the fourth annual 5K at Luck Stone Rockville on 26 September 2026, featuring a course through a working quarry and a post race zone with vendors, music, raffles, and family activities.

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.

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 fall trail event at Pohick Bay Regional Park offering 5 km and 10 km race options plus virtual entries; walkers are welcome and multiple registration tiers are available.

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.