Trail Running calendar near Warren County 2026-2027

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.

Event at Laurel Hill Park on October 17, 2026 offering 5K, 10K, half marathon and virtual options; walkers welcome and tiered registration fees.

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 on a flat, USATF certified C&O Canal Towpath course starting and finishing at Fletcher's Cove in Washington DC with aid stations and finisher medals.

Evenstar Ultras is a timed trail event at Shenandoah River State Park with 3, 6, 12 and 24 hour options on a 3.48 mile loop. Frequent returns to the main aid station reduce the need to carry heavy gear.

Scenic road and trail running in Prince William Forest Park with 5K, 10K, half marathon and virtual options for runners and walkers.

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 with 5 km and 10 km courses, kids races, spectator access, and lodging discounts across two days in October 2026.

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 5 km and 10 km races plus several virtual entry options at Conway Robinson State Forest on October 25, 2026; 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.

Scenic 5 km and 10 km races through Burke Lake Park on October 31, 2026, with in-person and virtual entry options; walkers and strollers are welcome.

Trail race in Little Orleans MD on November 1, 2026 offering 50K and 25K courses through Green Ridge State Forest with multiple aid stations.

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.

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 5 km and 10 km races at Burke Lake Park on November 7, 2026, with walkers welcome and virtual entries offering medal and shirt options.

Trail ultramarathon at Sherando Lake VA on Nov 7 2026 offering 40, 20 and 10 mile courses across singletrack and mountain ridgelines with staffed aid stations.