Trail Running calendar near Leonardtown 2026-2027

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.

Run or walk the trails at Pohick Bay Regional Park on October 4, 2026, with in-person 5K and 10K options plus several virtual entry choices and tiered registration fees.

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.

Multiple in-person and virtual races take place October 17, 2026 at Laurel Hill Park Central Green in Lorton, VA, with 5K, 10K, half marathon and walker-friendly options.

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.

Scenic, flat 5K and 10K at Bluemont Park in Arlington on October 17, 2026 with in person and virtual options; walkers and strollers are welcome.

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.

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 in Patapsco Valley State Park offering in-person and virtual 50k and 25k options, finishers awards including a hand-thrown mug, five aid stations, and a virtual completion window from Oct 24 to Nov 24, 2026.

A 24-hour loop endurance race in Williamsburg, VA on certified 2.215-mile loops, with distance awards, on-site support, team tracking, and proceeds benefiting The Arc in Williamsburg.

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 run at Conway Robinson State Forest in Gainesville, VA offering 5 km and 10 km distances plus virtual options with medals and shirts.

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.

Halloween-themed 5k and 10k at Indian Fields Tavern/5 Fields Brewing Co. with costume judging, official timing, finisher medal and a finish-line beer.

A 5k along the Virginia Capital Trail in Rocketts Landing, VA on October 31, 2026 with in-person and multiple virtual entry options.

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.