Trail Running calendar near Derwood 2026-2027

In-person 5K and 10K races at Leopold’s Preserve in Broad Run on August 23, 2026, with virtual entry options and registration tiers. The event is part of the Sippin Series in conjunction with the Farm Brewery at Broad Run; walkers welcome.

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.

A self-timed 5 miles on a packed rail trail in Darlington, Maryland, held as part of the Harford County Running Club Dog Days of Summer Series. The course is stroller friendly with parking at Fisherman's Log and free registration.

A trail event at Dirt Farm Brewing in Bluemont offering 5K and 10K courses over rugged, hilly terrain on August 29, 2026. Virtual entries are available with medal and shirt options.

A family-friendly 5K mud run on August 29, 2026 at Budds Creek Motocross Park featuring obstacles, mud pits, a pre event warm up, and an after party with music and food. Value and VIP registration options are available.

A community trail festival at Furnace Run Park in Shippensburg on August 29, 2026, featuring a one loop 5 kilometer race and a 1 mile event with chip timing and varied trail surfaces. Proceeds benefit Friends of Shippensburg Community Parks..

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 self-timed loop-trail event in Havre de Grace on 08/30/2026 with a listed distance of 3 miles. Runners have 90 minutes to complete as many loops as they like; parking is at Steppingstone Farm Museum.

Opening Night on September 4, 2026 at Morven Park in Leesburg, VA is a cross country meet for middle and high school teams. The event features a fast, spectator friendly course with music and food for a festival atmosphere.

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 four-part community trail series with three morning gatherings and a final sunset event in Marietta and Lancaster County. Participants choose their own distance, share food and hydration, and may register per event or buy a multi event pa..

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.

Tails on Trails 5K Run/Walk is the second annual 3.1 miles run, walk, and virtual event at Cacapon State Park on September 12, 2026. The wooded cross country course passes the upper lake and ends with awards and a free pup swim.

A women only trail running event at Fountainhead Regional Park on September 13, 2025 offering a half marathon and a 10k plus option. The event includes organized training runs and a course video; entry is closed.

Trails 4 Tails at Codorus State Park near Hanover, PA offers a 40 mile ultra, a 40 mile team relay, and a 25K on multi-loop trail courses with varied terrain and fully stocked aid stations.

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.

A looped trail event at Seven Bends State Park featuring roughly 10 mile loops on mixed terrain and multiple distances from 10 mile to 100 mile plus a Last Man Standing Ruck. Cutoffs, pacer rules, and awards vary by distance.