Trail Running calendar near Leonardtown 2026-2027

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 event in Prince William Forest Park on a 6.5 mile figure eight loop, featuring varied single track and fire road, two aid stations, and a limited field.

Fall Harvest 5k is a trail 5 km race at Claude Moore Park in Sterling, VA on October 3, 2026. The event includes an in-person 5K and several virtual entry options, and published fees include mandatory charges; promo codes are not accepted.

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.

Experience a unique trail run through 1600 acres of former prison grounds at Laurel Hill Park. Choose between 5.4 or 10 mile distances on scenic singletrack featuring historic guard towers and open meadows.

A trail event at Pohick Bay Regional Park on October 4, 2026 offering 5 km and 10 km courses plus virtual participation options. Walkers are welcome.

A Halloween themed 4 mile trail run and hike at York River State Park on October 10, 2026. The new trail features single track, river views and rolling hills, with finisher medals for all and a two hour time limit.

A community trail event on October 11, 2026 at Bretton Woods Recreation Center in Darnestown, MD offering a 5K trail run and a 1 mile walk. The event raises funds and awareness for addiction prevention, education, and support.

A technical trail 10K at Black Hill Regional Park with rocky and rooty terrain. The race is part of a low key series, free for club members and available to non members for a fee with on site bib and chip pickup.

A scenic, flat 5K and 10K at Bluemont Park in Arlington on October 17, 2026. Walkers and strollers are welcome and virtual entry options include medal and shirt choices.

Experience the scenic singletrack trails of Lake Fairfax Park with 5 mile and 10 mile race options. Enjoy a community atmosphere with post race breakfast and a dedicated program for children.

Community trail event at Camp Barnes in Frankford, Delaware offering 6.2 and 3.1 mile runs, 1 to 3 mile family walks, and a Kiddie Color Run. Post race lunch and live bluegrass music support Mariners Bethel youth ministries.

A trail event at Patapsco Valley State Park with in person and virtual 50k and 25k options, event swag, aid stations, and a finishers mug or medal.

A 24 hour loop endurance race in Williamsburg, VA on October 24, 2026. Runs use a certified 2.215 mile crushed gravel loop with distance awards and proceeds benefiting The Arc.

A marked trail competition in Prince William Forest Park offering a 25 km one loop and a 50 km two loop option with on course aid stations. Entry opens September 15, 2026 and the field is limited to 110 runners.

A trail event at Conway Robinson State Forest Park on October 25, 2026, offering 5K and 10K in-person races plus virtual entries with medal and shirt options. Walkers are welcome.

Scenic 5K through vineyard and farm at Rocklands Farm Winery with chip timing, age group awards, and a post-race wine tasting with live music. Walkers and children are welcome and a one hour course time limit applies.

A 5K at Rocketts Landing on October 31, 2026, with a course along the Virginia Capital Trail and views of the James River; virtual options are available with different kit choices.

Experience a mix of twisty singletrack and open farm field running in Germantown. This late autumn trail event offers three distances and a festive post race atmosphere at the historic Button Farm.