Trail Running calendar near Stephens City 2026-2027

District 19 in Anacostia on October 4, 2026 is a run crew led, unsanctioned road and trail event offering 5K, 19K and 19 Mile options with course markers, corral seeding, and a shirt, snack, and medal for finishers.

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.

Experience the beauty of Western Maryland at Rocky Gap State Park with 25K and 50K trail races. Run solo or join a relay team to navigate three distinct loops featuring scenic lake views and ridge traverses.

A community trail event on October 11, 2026 at Bretton Woods Recreation Center in Darnestown, MD offering a 5K trail run and a 1 mile walk. The event raises funds and awareness for addiction prevention, education, and support.

Participate in a 10 km run through the scenic Black Hill Regional Park in Boyds. This low key event offers a straightforward racing experience for both club members and the general public in a natural park setting.

Harvest Hills on October 17, 2026 features 5K, 10K and a half marathon at Laurel Hill Park in Lorton, VA. Walkers are welcome and virtual entry options are offered with medal and shirt choices.

The Annual Boulder Dash at Pinesburg Quarry in Williamsport, MD on October 17, 2026 offers three distances : 5 miles, 5K and 1 mile, and the quarry will be closed during the event for safety.

Marathon and half marathon at Fletcher's Cove on the C&O Canal Towpath, featuring a mostly flat, Boston-qualifying out-and-back course with riverside views, organized by the Safety And Health Foundation with cash and age-group awards.

Timed trail running at Shenandoah River State Park on a 3.48 mile loop with 670 ft of gain. Four time-based options from 3 to 24 hours, supported aid station, event hoodie, and awards including a special 100 mile recognition.

A scenic, flat 5K and 10K at Bluemont Park in Arlington on October 17, 2026. Walkers and strollers are welcome and virtual race options are available with and without medals and shirts.

Experience the scenic singletrack trails of Lake Fairfax Park with 5 mile and 10 mile race options. Enjoy a community atmosphere with post race breakfast and a dedicated program for children.

Obstacle course races at Massanutten Resort on October 24 and 25, 2026, featuring 5K and 10K distances plus a kids race, spectator tickets, team entry options, lodging discounts, and service member discounts.

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 5K and 10K at Conway Robinson State Forest in Gainesville, VA on October 25, 2026. Walkers are welcome and virtual entry options with medals or shirts are available, with fees that vary by registration date.

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 race in Little Orleans, Maryland on November 1, 2026 offering 25K and 50K courses on mixed trail and road terrain, multiple aid stations, official cutoffs, training runs, and a series reward program.

Experience a mix of twisty singletrack and open farm field running in Germantown. This late autumn trail event offers three distances and a festive post race atmosphere at the historic Button Farm.