Trail Running calendar near Woodstock 2026-2027

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.

A three day stage race around Spruce Knob in Circleville WV featuring a 50k, a 50 mile, a 13.1 mile half marathon and a 5k. Registration opens May 1 and closes August 16, 2026.

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.

A natural-surface 10K at Black Hill Regional Park with rocky, root-strewn trails and varied terrain. Part of MCRRC's low-key series with free entry for members and paid registration for non-members.

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..

Andy's Backyard Ultra is a last person standing ultra at Teventrails in Earlysville, VA where runners complete a 4.17 mile loop each hour. The final finisher is the runner who completes one more lap than all other entrants.

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.

A community fundraising trail event at Crozet Park offering a 5K, a limited 10K with a creek crossing, and a 0.75-mile family run. The day includes T-shirts, a pancake breakfast, a post-race festival, live music and proceeds for local trail..

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.

Trail running in Green Ridge State Forest near Little Orleans, MD, with 50K and 25K options. The 50K is about 31.95 miles out-and-back with seven aid stations; the 25K mixes technical trail and forest service roads.

Trail races at Button Farm in Germantown, MD on November 7, 2026 feature twisty singletrack and open farm fields, with distances of 13.5, 6.7 and 3.2 miles. The event includes aid stations, portajons, finisher medals and post-race food.

A multi distance trail event in Montebello VA with 100K, 50 Miler and 50K courses through Blue Ridge single track, logging roads and National Forest terrain around peak fall foliage.

Experience a 50 mile trail race through the scenic Seneca Greenway and Muddy Branch trails in Maryland. This event features forested single track terrain and small stream crossings for dedicated distance runners.

Trail races at Walnut Creek Park on November 8, 2026 offering 5K and 10K distances plus virtual entries with medal and shirt options. Registration fees vary by entry type and by registration date.