Trail Running calendar near Winchester 2026-2027

Riverside 8k and 16k in Potomac on February 28, 2027, with courses along the Potomac River and the C&O Canal path running north; nearby waterfalls and virtual participation options are available, and walkers are welcome.

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.

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.

A Last Runner Standing backyard ultra in Lorton, VA on March 20, 2027, using a 4.167 mile (6.7056 km) hourly loop with a limited 65-runner field, chef-supported aid, and entry by Ultrasignup waitlist.

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.

Run to Remember in Sykesville uses a 5.25 mile loop at Piney Run Park for 50K, 25K, a 5 miler and an 8 hour challenge. Fees include park entrance, a custom ice bandana and a commemorative mug.

A single-day endurance walk at Massanutten, VA on April 17, 2027 offering 7, 14, 21 or 28 mile options with a ten hour cutoff. Participants may ruck with 10, 20 or 35 pound vests and choose an advanced ridgeline route when conditions allow.

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 ultramarathon on the C&O Canal towpath in Knoxville, MD with start and finish at Camp Manidokan. The course is one 40 mile loop plus two 30 mile loops, with multiple aid stations and extensive riverside scenery.

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 5k & 10k in Bluemont VA features scenic, hilly trail courses with technical terrain around the property; runners can enter in-person 5 km or 10 km races or choose virtual options with medal or shirt.

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 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.