Trail Running calendar near Hillsboro 2026-2027

A 33.3 mile single loop trail run in the George Washington National Forest featuring a climb of Big Schloss with 360 degree views and three aid stations. Entry is limited to 60 runners and opens August 3, 2026.

A community 5K on September 26, 2026 that raises funds for cancer research and support, followed by an after party hosted by Independent Brewing. The event features race day raffles, a ghost runner option, and memorial recognition.

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.

A 110 miles trail ultramarathon in the Massanutten range with 22,300 feet of climbing and a 48 hours limit. The reverse MMT route uses rugged singletrack, includes two climbs of Waterfall, and requires crew support for the second half.

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.

Experience a technical trail race with your dog at a scenic equine rehabilitation facility in Virginia. Enjoy distances from 1.25 miles to 10K followed by a finishers festival with food trucks and a biergarten.

A 12 hour trail run at Prince William Forest Park featuring a 6.5 mile figure eight loop on single track and fire road, two aid stations, and options for solo or two person relay teams.

Trail races at the Workhouse Arts Center in Lorton VA on October 4, 2026. Options of 5.4 or 10 miles on mostly singletrack through forest and meadow across the former prison grounds.

A fall trail event at Pohick Bay Regional Park offering 5 km and 10 km race options plus virtual entries; walkers are welcome and multiple registration tiers are available.

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 trail event at Rocky Gap State Park on October 11, 2026 featuring three looping trails with varied terrain and elevation. Options include 25K, 50K, and relay teams of two or three with on-course and base camp aid stations.

A trail-based community event on October 11, 2026 at Bretton Woods Recreation Center featuring a 5K run and 1 mile walk to support the Michael Long Memorial Fund and addiction prevention and recovery services.

Running event at Pinesburg Quarry in Williamsport, MD on October 17, 2026 offering a one mile fun run, a 5K, and a 5 mile race. The course runs in and around the quarry which will be closed for the event.

A trail run at Lake Fairfax Park in Reston, VA offering **5.1 mile** and **10 mile** singletrack courses with lake views, short technical sections, on-site bathrooms, a kids program, race swag, and optional finish medals.

A weekend of obstacle races at Massanutten Resort on October 24-25, 2026 with Sprint 5 km, Super 10 km and kids races on mountain trails featuring rocky terrain and steep climbs. Team entries can secure the same start time and eligible staf..

A trail ultradistance event in Patapsco Valley State Park near Baltimore on October 24, 2026, offering 50k and 25k distances plus virtual options through November 24. Race headquarters is at CCBC Catonsville, with aid stations and finishers..

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 races at Conway Robinson State Forest Park in Gainesville, VA on October 25, 2026 offering 5 km and 10 km courses plus virtual options with medal and shirt choices.

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.