Trail Running calendar near Middletown 2025-2026

The Tails on Trails 5K Run/Walk takes place at Cacapon State Park in Berkeley Springs, West Virginia. This early fall event features an easy 5K course along the Rock & Roll Trail, suitable for runners and walkers of all levels. The scenic trail highlights the natural beauty of the area, making it a..

The Vineyard Vista 10k is a scenic running event held at Muse Vineyards in Woodstock, Virginia, along the North Fork of the Shenandoah River. The course features a mix of cross-country trails through vineyards, paved road sections, and trails around Seven Bends State Park. Runners can choose between..

The 12 Hour Adventure Trail Run, held at Prince William Forest Park near Triangle, VA, is an endurance trail running event featuring a 6.5-mile figure-eight loop course. The course, set on 100% trails including single track and fire roads, offers approximately 650 feet of elevation gain per loop wit..

The Valley View Hard Cider Challenge Half is a scenic and challenging running event held at Valley View Farm in Delaplane, Virginia. The race features a half marathon, 10k, and 5k distances, with courses combining cross country, trail, and hilly terrain. The half marathon is an out-and-back route co..

The Grindstone Running Festival by UTMB is a premier trail running event held in the scenic Shenandoah Valley, Virginia, featuring challenging courses through the George Washington and Jefferson National Forests. Set against stunning fall foliage and mountain views, the festival offers four race dis..

The Final Countdown Tribute is a unique running event held at Amani Brewing in Martinsburg, WV. The race features a 1.33-mile loop on a smooth, well-maintained grass trail with gentle hills. Runners must complete each lap within a decreasing time limit, starting at 20 minutes and shortening by 20 se..

The Woodstock Warrior is an endurance trail running event held at Seven Bends State Park in Woodstock, Virginia. It features a challenging 10-mile loop course with mixed terrain, including gravel roads, two-track dirt roads, and single-track trails, with approximately 1,800 feet of elevation gain pe..

The Laurel Ridge Community College 5K is a multi-surface, cross-country run/walk event held on the Middletown campus of Laurel Ridge Community College. The race starts and finishes outside the Student Union Building on Garland Snapp Drive. The course includes running in front of the school, a shorte..

The Brandy Station Battlefield 10k is a trail running event held at Brandy Station Battlefield in Virginia. The course combines cross country terrain with gravel dirt roads, featuring slight elevation gains but no major climbs. Runners can choose between 5k and 10k distances, with the 10k route bein..

The Lake & Leaf Shuffle is a trail running event held at Deep Creek Lake State Park in Swanton, Maryland, typically scheduled in late September to coincide with peak fall foliage. Participants can choose between a 6-mile single loop or a 12-mile double loop on scenic trails, offering a challenging a..

The River's Edge Endurance Challenge, held in Brunswick, Maryland, is a multi-event running competition featuring a 5K (3.1 miles) race, a 3-hour endurance race, and a 6-hour endurance challenge. The event takes place primarily on the scenic River's Edge Trail system, with about one mile on school p..

The Fox Trot 5k in Keswick is a scenic cross-country race held at Merrie Mill Farm & Vineyard. The event features a 5k course that includes a mix of flat gravel, dirt, paved roads, and some notable hills, offering a varied terrain for runners. Participants also have the option to run a 1-mile distan..

The Run to the Taproom - Creekside Farm Brewery 5K & 8K is a scenic running event held at Creekside Farm Brewery in King George, Virginia. Participants can choose between a 5K or 8K race along well-maintained, non-technical dirt trails that wind through a 1,000-acre farm bordering the Rappahannock R..

The West Virginia Trilogy is a challenging three-day stage race held in Circleville, WV, on Spruce Knob, the state's highest peak, within the Monongahela National Forest. The event features three distances: a 50-kilometer run on day one, a 50-mile run on day two, and a 13.1-mile half marathon on day..

The Full Distance 10k is a scenic trail running event held at Locust Shade Park in Triangle, Virginia. The course features a mix of trails and pavement, with about 40% paved and some hills, consisting of four loops for the 10k distance. This chip-timed race welcomes both runners and walkers and is p..

The Trails 4 Miles is an annual trail running event held at Sherando Park in Stephens City, Virginia. The main race is a challenging 4-mile course featuring mixed surfaces, including paved paths and wooded trails through the scenic Sherando Park Mountain Bike Trails. Runners experience beautiful fal..

The Rick O'Donnell Memorial Ultra Challenge is an annual trail running event held in Mount Airy, Maryland, hosted by the Frederick Steeplechasers Running Club. The event features three race options: a 5-mile trail run, a 4-hour challenge, and an 8-hour ultra challenge, offering various ways for runn..

The Rocky Gap Trail Run, hosted by EX2 Adventures at Rocky Gap State Park in Flintstone, Maryland, offers challenging 25K and 50K ultra-distance trail races, including relay options for teams of 2 or 3. The course features three distinct loops ranging from 4.4 to 6.5 miles, with varied terrain inclu..

The Wilderness Run 10k is a scenic cross-country trail race held at Wilderness Run Vineyard in Spotsylvania, Virginia, situated on historic Civil War battlefields. The course features rolling hills, with the 10k consisting of two laps of the 5k out-and-back route. Participants enjoy a vibrant atmosp..

The Bivanna Trail Extravaganza is a trail running event held in Charlottesville, Virginia, featuring multiple race distances on the scenic Rivanna Trail. Participants can choose from a 40-mile full loop, a 20-mile half loop (Demibivanna), a 10-mile quarter loop (Hemidemibivanna), or a 40-mile biking..