Trail Running calendar near Warrenton 2026-2027

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.

Leopold’s Preserve 5k & 10k in Broad Run, VA on August 23, 2026 features 5 km and 10 km distances, welcomes walkers, and offers virtual entry options with medal and shirt choices.

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 race at Dirt Farm Brewing in Bluemont VA offering 5 km and 10 km routes plus virtual options. The courses run on rugged, winding trails with steep climbs and descents through rural landscapes.

The Muddy Dash - Maryland will take place in Wicomico Shores on Saturday 29 August 2026.

A community running event at Albemarle CiderWorks on August 30, 2026 offering 5K and 10K courses plus virtual entries. The course is listed as new for 2025 and cider will be available after the race.

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.

Opening Night 2026 at Morven Park in Leesburg, VA opens the cross country season with races for middle and high school divisions, a spectator friendly course, music and food. Course updates and awards info will be announced in May 2026.

A 5K and 10K held at Fifty-Third Winery & Vineyard in Louisa, Virginia on September 5, 2026 with in-person and virtual options. Proceeds support Hooves & Paws Animal Rescue and its sanctuary work.

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.

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 multi-distance trail running festival in the Shenandoah Valley offering 100M, 100K, 50K and 21K races on technical mountain terrain with UTMB World Series and Western States qualification.

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 event at Seven Bends State Park with a roughly 10 mile mixed terrain loop and distances from 10 mile to 100 mile plus a Last Man Standing Ruck. The event uses sequential cutoffs, has specific pacer rules, and aid station drop procedur..

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 at Sherando Park on September 26, 2026 features a mixed-surface four-mile trail race, an untimed one-mile out-and-back on a paved path, and a new 5.3 mile mountain bike time trial, with proceeds to the I’m Just Me Movement.

A 33.3 mile single loop trail run in the George Washington National Forest featuring a climb of Big Schloss with 360 degree views and three aid stations. Entry is limited to 60 runners and opens August 3, 2026.