Trail Running calendar near Winchester 2026-2027

Scenic 5K and Half Marathon along the Chesapeake & Ohio Canal in Georgetown with in-person and virtual entry 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 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.

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 community trail festival at Furnace Run Park in Shippensburg on August 29, 2026, featuring a one loop 5 kilometer race and a 1 mile event with chip timing and varied trail surfaces. Proceeds benefit Friends of Shippensburg Community Parks..

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.

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

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.

Mountain trail event on Blue Knob near Claysburg offering 10K, half-marathon and 50K courses with significant elevation and technical rocky terrain. Aid stations, a swag package, and post race food and beer are provided.

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.