Trail Running calendar near Winchester 2026-2027

Four weekly 10K trail runs in May 2026 at the Pickall Area of Patapsco Valley State Park, organized by park stewards and timed by running time. Local sponsors support the series and Friends of PVSP members receive a $27 series discount.

A backyard style ultra in Knoxville MD on May 30, 2026 where runners complete a 4.167 mile loop each hour until one remains. A 1 mile event runs for 24 hours with additional tie breaker miles if needed.

A 5k and 1 mile trail event at Gentle Giants Draft Horse Rescue in Mt. Airy, MD on May 30, 2026. The route crosses a 340 acre farm with draft horses nearby and features food trucks and mounted archery demonstrations.

ROCK CREEK 100 is a 100 mile looped trail event near Washington D.C. held May 30–31, 2026, consisting of ten 10 mile loops with about 8,200 ft of climbing and a 36 hour cutoff.

A scenic loop at Sky Meadows State Park on May 31, 2026, offering 5K and 10K courses with views of fields, streams and Turners Pond. Walkers are welcome and virtual entries are available with medal and shirt options.

Experience the FXBG Trail 5 Miler at Motts Run Reservoir in Fredericksburg. This five mile trail race features three distinct climbs and over 300 feet of elevation gain along a scenic and flowing course.

A measured 100 mile loop in Fort Valley, Virginia, through the Massanutten Mountains and Shenandoah River Valley with 14 climbs and about 14,000 feet of elevation gain. There is a 24 hour cutoff for the silver buckle and 28 hours to finish.

A longstanding five-mile memorial run on the C&O Canal Towpath in Williamsport, MD, held June 6, 2026, with regular and student entries, chip timing, technical T-shirts, and awards for podium finishers.

Trail races in Colonel Denning State Park offering a rugged 15K and 25K with substantial elevation gain, limited to 120 runners and supported by multiple aid stations.

A community fundraising day at Burke Lake Park with a chip-timed 5k run and a noncompetitive 2k walk. The event supports programs for people with intellectual and developmental disabilities and includes awards, shirts, and post-event festiv..

A night trail event in Prince William Forest Park offering a 50+ mile race made of two laps of a 25+ mile loop, plus 25M and 10M options. Aid stations are placed on course and crews are restricted to the Telegraph Road Pavilion.

A community 5K and 1 mile Fun Run in Warrenton, VA that raises funds for Fauquier Education Farm, a 501(c)(3) that advances agricultural education and donates its harvest to local food banks.

Trail races on June 19, 2026 in Germantown, MD offering 6K and 12K courses around Button Farm and the Schaeffer Farm Trails. Walkers and several virtual entry options are available.

Experience a 40 mile ultramarathon through the Monongahela National Forest and Dolly Sods Wilderness. This trail run features the natural beauty of West Virginia with a route based around the Canaan Valley Resort State Park.

A rugged out-and-back trail race near Frederick, MD, offering a 50K and a 25K Half Cat on rocky, shaded singletrack with stream crossings, three aid stations, and mandatory on-course hydration.

PUSO 5k & 10k on June 20, 2026 follows the Chesapeake & Ohio Canal path in Georgetown, Washington, DC. Runners and walkers can choose either a 5 km or 10 km distance, with registration fees varying by period.

A trail race in Canaan Valley State Park on June 27, 2026 with one loop of 5.9 miles or two loops for 11.8 miles on the Promised Land Trail, about 350 feet elevation gain per loop. Field is limited to 200 runners.

Kick off the Blue Crab Bolt series at Seneca Creek State Park with scenic 5K and 10K trail runs featuring lake views and singletrack paths. Enjoy professional race support, post-run breakfast burritos, and a festive atmosphere.

A 12 hour trail event on a scenic five mile single track loop in Berkeley Springs WV, featuring technical terrain with about 750 feet elevation per loop, on-course aid stations, a post race meal and handcrafted awards.

MCRRC Cross Country on the Farm Trail 5K is a trail race at Agricultural History Farm Park in Derwood MD. Non member registration is available for a $20 fee and the event is part of the club's low key race series.