Trail Running calendar near Leonardtown 2026-2027

An outdoor adventure race in Midlothian, VA on October 3, 2026 where participants use a map to find 5 to 7 hidden control points and collect tokens. First three finishers with all tokens are champions and a portion of proceeds supports Semp..

Join this annual community trail run through the wooded trail network of Potomac Shores. Residents and guests can choose between 5K and 10K courses for a free morning of outdoor activity in Dumfries.

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.

In-person 5 km and 10 km races plus multiple virtual options at Pohick Bay Regional Park on October 4, 2026; walkers are welcome.

District 19 in Anacostia on October 4, 2026 is a run crew led, unsanctioned road and trail event offering 5K, 19K and 19 Mile options with course markers, corral seeding, and a shirt, snack, and medal for finishers.

First annual 4 miles trail run and hike at York River State Park on October 10, 2026. Dirt trails include single track and gravel, the format is non competitive, all finishers receive medals and leashed dogs are allowed.

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.

Participate in a 10 km run through the scenic Black Hill Regional Park in Boyds. This low key event offers a straightforward racing experience for both club members and the general public in a natural park setting.

Event at Laurel Hill Park on October 17, 2026 offering 5K, 10K, half marathon and virtual options; walkers welcome and tiered registration fees.

Marathon and half marathon on a flat, USATF certified C&O Canal Towpath course starting and finishing at Fletcher's Cove in Washington DC with aid stations and finisher medals.

A community event at Assateague State Park offering a 2 mile walk or 5K run to support the Macky & Pam Stansell House of Coastal Hospice.

Scenic road and trail running in Prince William Forest Park with 5K, 10K, half marathon and virtual options for runners and walkers.

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.

Trail ultramarathon in Patapsco Valley State Park offering 50k and 25k options, in-person and virtual, with aid stations, event shirt, and finisher awards.

A 24-hour loop endurance race in Williamsburg VA on a USATF certified 2.215 mile crushed gravel course with multiple distance awards and on-site amenities.

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.

Trail 5 km and 10 km races plus several virtual entry options at Conway Robinson State Forest on October 25, 2026; 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.