Trail Running calendar near Williamsport 2026-2027

A trail 5K at Claude Moore Park in Sterling, VA on October 3, 2026, featuring forest and leaf-covered trails and serving as the fourth race in the Run Your PRCS Parks timed series. In-person and several virtual entry options are available.

The 20th annual Cumberland Valley TrailFest in Shippensburg features a half marathon, 5k, hikes, a 25 mile bike ride and a 1 mile fun run on the Cumberland Valley Rail Trail. Proceeds benefit the Cumberland Valley Rails-to-Trails Council.

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.

Run or walk the trails at Pohick Bay Regional Park on October 4, 2026, with in-person 5K and 10K options plus several virtual entry choices and tiered registration fees.

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 at Laurel Hill Park in Lorton, VA on October 17, 2026 offers 5K, 10K and half marathon distances with in person and virtual options and tiered entry fees; walkers are welcome.

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 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.

An in-person 5 km and 10 km event at Bluemont Park in Arlington on October 17, 2026, with flat courses and walker-friendly access. Virtual entries are available with several medal and shirt 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-supported trail race of about 5.25 miles at Gunpowder State Park featuring a steep opening climb, varied downhills and scenic single track. It is the shortest event in the BRRC trail series and offers race day registration.

Trail ultramarathon at Patapsco Valley State Park offering 50k and 25k distances with in person and virtual options. Participants receive a Brooks event shirt, on-course aid stations, and a hand-thrown mug or finishers medal.

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 themed, untimed trail event at Camp Anderson on October 24, 2026 where runners wear flag belts and navigate zombie zones. The event features runner and zombie roles, costume encouragement, awards, and proceeds benefiting local organizatio..

Trail races at Conway Robinson State Forest on October 25, 2026, offering 5 km and 10 km trail distances plus virtual options with medal and shirt choices; 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.

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..