Trail Running calendar near Annandale 2026-2027

A self-timed 5 miles on a packed rail trail in Darlington, Maryland, held as part of the Harford County Running Club Dog Days of Summer Series. The course is stroller friendly with parking at Fisherman's Log and free registration.

Trail event at Dirt Farm Brewing in Bluemont VA offering 5K and 10K courses over rugged terrain with virtual entry options on August 29, 2026.

Scenic 5 km and 10 km races on the trails of Mason District Park in Annandale, with in-person and virtual entry options on August 29, 2026.

Family friendly mud run at Budds Creek Motocross Park on August 29, 2026 featuring a 5K course with obstacles, mud pits, slides and a festival style after party.

A 3.8 mile running event at Pen Mar Park that climbs about 1.8 miles to High Rock Overlook and returns to the park. Registered finishers receive an official High Rock Mountain t-shirt and there are early and race day fee options.

A 3 mile cross country race through Nottoway Park in Vienna, VA on 08/30/2026 with a kids dash and a club picnic that includes food and drinks. Registration is free for members and $10 for nonmembers.

A self-timed loop-trail event in Havre de Grace on 08/30/2026 with a listed distance of 3 miles. Runners have 90 minutes to complete as many loops as they like; parking is at Steppingstone Farm Museum.

Cross country at Morven Park with a high school invitational plus an open 5K, featuring food trucks, music and a spectator friendly course.

Annual running event at Fifty-Third Winery & Vineyard in Louisa VA offering 5 km and 10 km races plus virtual options to benefit Hooves & Paws Animal Rescue.

A 71 miles clockwise circuit of the orange-blazed Massanutten Trail with multiple aid stations, mandatory qualifications, and strict cutoffs on a rocky, high-ascent route.

A 10K road race and a 5K road/trail combo at the Shrine of St Anthony in Clarksville, MD on Sept. 5, 2026. Both USATF certified with chip timing, guaranteed shirts for early registrants, music and family activities.

Trail races at Mount Vernon District Park on September 6, 2026 offering 5 km (two laps) and 10 km (four laps) routes, with in-person and virtual entry options.

Carderock Charge offers 5K, 10K and a half marathon on the flat C&O Canal Towpath in Potomac, MD on September 6, 2026.

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.

Scenic trail 5K and 10K around Burke Lake Park in Fairfax Station on September 7, 2026, with in-person and virtual entry options.

A 5K and half marathon along the Chesapeake and Ohio Canal towpath in Georgetown with in-person and virtual entry options.

A chip timed trail race at South Branch Farms offering 5K and 10K routes on varied terrain with creek crossings, climbs, wildlife sightings, and a post race gathering. Proceeds support the Farm and Natural Lands Trust of York County.

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 second annual 5K at Cacapon State Park benefiting the Humane Society of Morgan County, offering in-person run and walk options plus a virtual entry. New course, awards ceremony, and a free post race pup swim in the lake.

A women only trail event at Fountainhead Regional Park offering a half marathon and a 10k plus on September 12, 2026. Registration runs June 8 to September 1 and two training runs are scheduled in August.