Trail Running calendar near Middletown 2026-2027

In-person 8k and 16k races along the Potomac River and C&O Canal path in Potomac, MD, with virtual options and post-race waterfall views.

An annual eight hour timed trail event on a 5.5 mile loop at Little Bennett Park in Clarksburg, MD with mostly single-track trails.

A women only trail endurance event in Triangle VA offering 25K and 50K courses with two loops, stocked aid stations, and a nine hour cutoff.

The Elizabeth Furnace 50 km is a technical mountain trail race in the Massanutten range covering 30.5 miles and about 6,400 feet of ascent. Aid is limited with staffed stations near 10 and 22 miles so runners must carry personal supplies.

St. Patrick's Half & Marathon on March 14, 2027 in Georgetown features scenic courses along the Chesapeake & Ohio Canal and a Boston qualifying full marathon.

Test your limits in Lorton at this elite backyard marathon featuring dedicated day and night loops. With a limited field of 65 runners and a chef supported aid station, it is the perfect venue for a personal best.

A 14 mile untimed point to point trail run along the Dahlgren Railroad Heritage Trail that starts at one Sheetz and finishes at another. The event features unusual aid station snacks and practical finisher swag.

A 50 mile trail race near Clifton, Virginia on April 4, 2027, run over forested, rolling terrain in spring. Entry opens October 1, 2026; the race has a 13-hour limit and a $125 entry fee.

A timed mountain trek at Wisp Resort offering 7, 14, 21, and 28 mile loop options with a 10 hour limit; well marked trails, optional weighted vests for bonus swag, and finishers receive a shirt, patch, and medal.

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 single-day endurance walk at Massanutten offering 7, 14, 21, and 28 mile options, optional ruck weights, and a choice of western slope or advanced ridgeline terrain.

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 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.

Flat marathon and half marathon along the C&O Canal Towpath at Fletcher's Cove in Washington, DC. The mostly crushed gravel out and back course offers shaded river views, aid stations, and monetary prizes for top finishers.

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.

A 100 mile trail ultramarathon in the Massanutten Mountains featuring rocky trails, over 18,000 feet of climbing, a 36 hour cutoff, and on course support and training runs.

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.