Trail Running calendar near Derwood 2026-2027

An evening three hour loop event at Roundtop Mountain Resort in Lewisberry, PA featuring a 1.5 mile loop with 600 feet of elevation gain and a separate kids race of about one mile. Pogs are awarded per lap and top finishers receive slammers..

A 7K trail race at the Woodstock Equestrian Center with a hilly course that circles fields and runs through wooded single track, presented as a 1969 throwback with 60s music and period attire encouraged.

A memorial 5K trail run at Genesee Valley Outdoor Learning Center in Parkton, MD, with a 5K, 1-mile walk, kids dash, team entries, and an In Spirit donation option. Proceeds support a scholarship fund and a post-race festival offers food an..

A 5K and 10K event at Leopold’s Preserve in Broad Run on August 23, 2026, offering in-person and virtual options and included in the Sippin Series with the Farm Brewery at Broad Run.

Experience an engaging 8 mile trail race through the winding singletrack of Fredericksburg. Navigate rolling hills and punchy climbs in this focused event supported by the local running community.

Trail-style 5K and 10K at Dirt Farm Brewing in Bluemont, VA on August 29, 2026, featuring rugged terrain, steep climbs, and virtual entry options with medals and shirts.

Muddy Dash Mechanicsville is a 5K mud run at Budds Creek Motocross Park with obstacles, mud pits and slides plus a festival style after party with music, food and beer. Registration options include standard and VIP packages.

An out-and-back 3.8 mile run at Pen Mar Park with about 1.8 miles of ascent to High Rock Overlook. Held August 30, 2026, with registration deadlines and a higher fee on race day.

Experience a cross country race through Nottoway Park followed by a community picnic. This event features a three mile course and a kids fun run to celebrate the end of the summer season.

A clockwise 71-mile circuit of the orange-blazed Massanutten Trail around Fort Valley, VA, with 13,500 ft of elevation change, scheduled aid stations, strict qualifications and enforced cut-offs; GPX and aid charts are provided.

A 10 mile trail race in Fredericksburg, VA that follows the Rappahannock River, moves through rolling hills, and finishes with a sustained climb. Top three men and top three women receive gift certificates.

Experience the 15th annual Sasquatch Preservation Trail Run in Seven Valleys. Choose between the 5K or 10K courses and explore the natural landscapes preserved by the Farm and Natural Lands Trust.

Run a scenic off road trail through a 1000 acre farm bordering the Rappahannock River. Enjoy a post race celebration at the brewery with live music craft beer and a souvenir pint glass.

A charity 5K at Cacapon State Park supporting the Humane Society of Morgan County, with running, walking, and virtual options. The course follows a high school cross country route through woods and past the upper lake, with a post race pup..

Trails 4 Tails at Codorus State Park offers a 40 mile ultra, a team relay and a 25K on a looped trail course that mixes pavement, fields, singletrack and shoreline, with aid stations, camping and a race day picnic nearby.

The Final Countdown Tribute at Amani Brewing in Martinsburg WV uses a 1.33 mile loop where allowed lap time shortens each circuit, eliminating runners until one remains.

Trail ultramarathons at Seven Bends State Park run on a roughly 10 mile mixed terrain loop, with distances from 10 miles to 100 miles plus a Last Man Standing Ruck. Cutoffs apply and specified pacer and aid station rules govern the event.

Three trail distances near Pine Grove Furnace State Park in Gardners, PA, featuring rocky single track, ridgelines, and multiple aid stations with varied nutrition options. Courses use trails in the northern Michaux State Forest.

An in-person event on September 26, 2026 in Brunswick, MD featuring a trail-based 5K and timed 3-hour and 6-hour challenges on a 5 mile loop. Proceeds support Brunswick High School Track and Field equipment.

Trails 4 Miles is an annual event at Sherando Park with a mixed-surface four mile trail race, an untimed one mile fun run on the paved path, and a new mountain bike time trial. Proceeds support the I'm Just Me Movement.