Trail Running calendar near Annandale 2026-2027

A 5K and half marathon along the Chesapeake & Ohio Canal path in Georgetown, Washington DC on August 16, 2026, with in-person and virtual participation options.

A 7K trail race at The Woodstock Equestrian Center in Dickerson, Maryland, presented as part of MCRRC's low key series for members. Non member registration has a $20 fee and runs from February 10, 2026 to August 16, 2026.

A four mile out-and-back run on the NCR Trail from the Paper Mill parking lot in Cockeysville on August 19. The event is part of the Baltimore Road Runners Club Grand Prix Series and is scheduled as a weekday evening club run.

A memorial 5K trail run at Genesee Valley Outdoor Learning Center in Parkton, MD, with a 5K, 1-mile walk, kids dash, team entries, and an In Spirit donation option. Proceeds support a scholarship fund and a post-race festival offers food an..

A 5K and 10K event at Leopold’s Preserve in Broad Run on August 23, 2026, featuring in-person and virtual options and a new Sippin Series partnership with Farm Brewery at Broad Run.

Experience an engaging 8 mile trail race through the winding singletrack of Fredericksburg. Navigate rolling hills and punchy climbs in this focused event supported by the local running community.

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.

A family friendly 5K mud run at Budds Creek Motocross Park on August 29, 2026, featuring obstacles, mud pits, slides, a Pre Party and an After Party with music and food. Standard and VIP registration options are available.

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 clockwise 71-mile circuit of the orange-blazed Massanutten Trail around Fort Valley, VA, with 13,500 ft of elevation change, scheduled aid stations, strict qualifications and enforced cut-offs; GPX and aid charts are provided.

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.