Trail Running calendar near Prince Frederick 2026-2027

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.

Scenic 5K, 10K and half marathon courses through Burke Lake Park trails with in-person and virtual entry options; walkers are welcome.

A community charity race in Gaithersburg on October 3, 2026, featuring cross-country 10K and 5K, a paved 1-mile accessible fun run, and a kids Trike-A-Thon. Proceeds support Comfort Cases and Covenant Life School and include a post-race bac..

Trail event at Prince William Forest Park with a 6.5 mile figure eight loop, a 30 km option, two aid stations, and an awards ceremony with a post race meal.

A trail 5K at Claude Moore Park in Sterling VA on October 3, 2026, offering in-person and virtual entries with medal and shirt options.

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 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.

A scenic chip-timed 5K on the 300+ acre Running Hare Vineyard in Prince Frederick, MD, featuring a complimentary drink for those 21 and over, live music, finisher medals, apparel options, and proceeds supporting Habitat for Humanity.

Experience a unique trail event at Milkhouse Brewery in Mount Airy featuring a 5 mile race and timed ultra challenges. Complete as many loops as possible over four or eight hours on this scenic farm course.

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.