Trail Running calendar near Herndon 2026-2027

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 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.

Autumn races at Laurel Hill Park on October 17, 2026 offering 5K, 10K, a half marathon and virtual options with varied entry 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.

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.

Fall Run for the Wounded on Oct 18, 2026 features 5K, 10K and a half marathon through Prince William Forest Park with in-person and virtual options.

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.

A donation-funded *5.25 mile* trail race at Gunpowder State Park on October 18, 2026, featuring a steep early climb, downhill sections, and single-track trail. No registration fee and race day registration is available.

A trail event in Patapsco Valley State Park offering in-person and virtual 50k and 25k options, finishers awards including a hand-thrown mug, five aid stations, and a virtual completion window from Oct 24 to Nov 24, 2026.

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.

Trail run at Conway Robinson State Forest in Gainesville, VA offering 5 km and 10 km distances plus virtual options with medals and shirts.

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.

The 5th Annual Mackyard Ultra is an ultramarathon hosted by the Baltimore Road Runners Club at Shawan Downs in Cockeysville on October 31, 2026. Entry is $20 and the field is limited to 100 runners with pre registration on RunSignUp planned..

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.

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.

A scenic trail 5k and 10k at Burke Lake Park on November 7, 2026, offering in-person and virtual options with medals and shirts available.

Run Through the Grapevine is an 8K cross country race at Linganore Winery in Mount Airy, Maryland on November 8, 2026. The course runs through vineyard rows and adjacent hop yards, and all finishers receive one free winery tasting.