Trail Running calendar near Middletown 2026-2027

Fall Harvest 5k is a trail 5 km race at Claude Moore Park in Sterling, VA on October 3, 2026. The event includes an in-person 5K and several virtual entry options, and published fees include mandatory charges; promo codes are not accepted.

Experience a unique trail run through 1600 acres of former prison grounds at Laurel Hill Park. Choose between 5.4 or 10 mile distances on scenic singletrack featuring historic guard towers and open meadows.

A trail event at Pohick Bay Regional Park on October 4, 2026 offering 5 km and 10 km courses plus virtual participation options. Walkers are welcome.

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.

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.

Timed trail event on a 3.48-mile loop in Shenandoah River State Park with 3-, 6-, 12-, and 24-hour options, on-course aid, awards, and required lighting for night segments.

A scenic, flat 5K and 10K at Bluemont Park in Arlington on October 17, 2026. Walkers and strollers are welcome and virtual entry options include medal and shirt choices.

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.

An obstacle race weekend at Massanutten Resort featuring Sprint, Super, and Kids races on rocky, mountainous terrain, with team registration, lodging discounts, and service member pricing available.

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..

A trail event at Conway Robinson State Forest Park on October 25, 2026, offering 5K and 10K in-person races plus virtual entries with medal and shirt options. Walkers are welcome.

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 races of 50K and 25K in Green Ridge State Forest near Little Orleans MD on November 1, 2026. The 50K is an out and back with multiple aid stations; the 25K mixes technical trail and forest service roads.

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.