Trail Running calendar near Washington 2026-2027

A turtle themed 5K at Hopkins Farm Brewery in Havre De Grace raising funds and awareness for the Susquehannock Wildlife Society. The trail race includes wooden participant medals, costume prizes, and an after party with live music.

A memorial running event at Piney Run Park near Sykesville offering 50K, 25K, a 5-mile loop, and an open 8-hour lap challenge with stocked aid stations.

A cross country 5K at Red Shedman Farm Brewery on the Linganore Winecellars grounds, with a technical quarter zip and one pour for finishers and on-site picnic and tasting options.

A 100 mile race along the C&O Canal towpath near Knoxville MD with a 40 mile loop plus two 30 mile loops, multiple aid stations, and a Camp Manidokan start.

A last person standing endurance race in York, PA where runners repeat hourly loops until one remains. Entries include a designated parking and crew area, an event shirt, and a certified distance card.

A trail running event at the Agricultural History Farm Park in Derwood, Maryland, featuring lap based 3, 6, and 10 hour Challenges and a conventionally timed marathon and 25K. Volunteers receive the same finishers' swag.

Trail Demon presents scenic, technical trail races of 5 km and 10 km near Foggy Bottom Road in Bluemont, VA on May 1, 2027, with virtual entry options.

Marathon and half marathon on the C&O Canal Towpath at Fletcher's Cove in Washington DC on May 1, 2027, featuring a mostly crushed gravel out and back course with river views.

The SCA 5K is a cross country 5 kilometer race on natural terrain held within Shalom Dutchfest. It offers multiple age divisions with medals, ribbons, and cash prizes, and early registrants receive a complimentary t shirt.

Shenandoah Sky in Bentonville, Virginia on May 15, 2027 offers a Mountain 25K with 1700+ feet of climbing, an 8 Mile trail race, and an untimed 8 Mile hike through river, valley, and forest single track.

Massanutten Mountain Trails 100 is a 100 mile trail ultramarathon in Virginia’s Massanutten Mountains with over 18,000 ft of ascent and a 36 hour cutoff.

Scenic loop 5K and 10K at Sky Meadows Turners Pond in Delaplane VA with views of fields and streams; virtual options and walkers are welcome.

A 24 hour Backyard ultra on Mason Neck with a 4.167 mile loop, 100 mile limit, single aid station, and a field capped at 100 runners.

Backyard-style ultra in Knoxville MD with repeating 4.167 mile laps every hour until one remains, plus a concurrent 1 mile Mortals edition.

A night-time trail event in Prince William Forest Park featuring a 25+ mile loop run twice for 50 miles, with staffed aid stations and park-specific crew and pacer rules.