Trail Running calendar near Keezletown 2025-2026

The Barrel Oak 6k is a challenging running event set in the scenic Barrel Oak Winery, featuring a cross-country route that includes gravel roads and hills. Participants can enjoy a fun atmosphere, with options for both runners and walkers, as well as leashed pets. The event supports the Semper Fi an..

The Old Dominion 100 Mile Endurance Run is a challenging ultramarathon held annually in Virginia, featuring a diverse course that includes various terrains such as pavement, gravel roads, and single-track trails. Established in 1979, this event emphasizes tradition and community, being entirely volu..

The Crooked Run Valley 10k is a scenic running event taking place in Sky Meadows, Delaplane, VA. Scheduled for June 8, participants can also opt for a 5k distance. The race features a challenging trail with roots and rocks, and runners will receive a finisher's medal, a technical event shirt, and ch..

The Jackson River Scenic Trail Marathon, Half Marathon, 10k, and 5k is a vibrant running event taking place in Covington, Virginia. Set along a USATF certified course, the race features a smooth, crushed gravel surface that is mostly flat with some gentle hills, winding through picturesque landscape..

The Highlands Sky 40 Mile Trail Run is a premier ultra-marathon event held in the scenic landscapes of West Virginia, specifically through the Monongahela National Forest and Canaan Valley State Park. Scheduled for June 14, 2025, this challenging race showcases the rugged beauty of the Roaring Plain..

The Canaan Valley Trail Run, scheduled for June 21, 2025, in Canaan Valley State Park, offers a scenic and exciting experience for runners of all levels. Participants can choose between a 5.9-mile single loop or an 11.8-mile double loop on the Promised Land Trail. Each runner will receive a finisher..

The Winery 10k is part of the 53rd Winery's annual running event, which also includes a 5k race. This event takes place at the scenic 53rd Winery in Louisa, Virginia, and features a cross-country course around the vineyards. Participants can enjoy a chip-timed race, receive a finisher's medal, a tec..

Leopold's Preserve 10k is a trail running event taking place at Leopold's Preserve in Haymarket, Virginia. Participants can enjoy a scenic course that features a mix of dirt paths and natural terrain. The event is part of a series where points are accumulated towards year-long competitions.Runners r..

The 868 Estate Vineyards 10k is a scenic running event taking place at the picturesque 868 Estate Vineyards. Participants can choose between a 5k and 10k distance, with both races contributing points towards various year-long series. Runners will receive a glass of wine, a finisher medal, a technica..

The Jarmans Invitational Marathon, held in Crozet, Virginia, is a unique and challenging 30-mile race that takes place on the first or second Saturday of August. The course features a steep gravel road with significant elevation gain, requiring runners to complete multiple laps. Participants can exp..

The Merrie Mill Farm & Vineyard 10k is a scenic running event taking place at the picturesque Merrie Mill Farm & Vineyard. Participants can enjoy a challenging course that includes notable hills, flat gravel, and paved roads. The event welcomes both runners and walkers, with a virtual race option av..

The Third Winchester Battlefield Half is a running event that includes a half marathon, 10k, and 5k, set in a scenic trail environment. Participants can enjoy a chip-timed race with finisher medals and technical event shirts. The event supports Operation Enduring Warrior, a nonprofit dedicated to ai..

The Orchard Dash 10k, taking place at Albemarle CiderWorks, offers runners a unique cross-country experience with a challenging course featuring hills. Participants can enjoy a post-race glass of cider, a finisher's medal, and a technical event shirt. The event supports Albemarle CiderWorks and incl..

The Inferno 10k is an exciting running event set in a challenging forest trail behind Dirt Farm Brewing in Bluemont, VA. Participants will navigate steep inclines, technical spots, and breathtaking landscapes, making for an exhilarating experience. Runners will receive a finisher medal, a technical..

The Odyssey Trail Running Rampage is an exciting trail running event taking place at Douthat State Park in Millboro, Virginia. Scheduled for September 6, 2025, the event features four race distances: a 50K Ultra, a Marathon, a Half Marathon, and a Six-Miler. Participants will experience challenging..

The Valley View Hard Cider Challenge Half is a running event held at Valley View Farm, featuring challenging courses that combine cross country, trail, and hilly terrain. Participants can choose from a half marathon, 10k, or 5k, with points awarded towards various year-long series. Runners receive a..

The Grindstone Running Festival by UTMB is an exciting trail running event set in the picturesque Shenandoah Valley, featuring courses through the stunning George Washington and Jefferson National Forest. Scheduled for September 19-21, 2025, the festival offers a range of distances including 100M, 1..

The Pawpaw 10 Miler and 5 Miler is an exciting running event taking place at Powhatan State Park, Virginia, as part of the annual Pawpaw Festival. This year marks the third edition of the race, which celebrates the park's 10th anniversary. Participants can choose between a scenic 10-mile course and..

The Brandy Station Battlefield 10k is a scenic running event taking place at the historic Brandy Station Battlefield. Participants can enjoy a combination of cross-country and gravel dirt road courses, featuring slight elevation gains. Runners receive a finisher's medal, a technical event shirt, and..

The Greenbrier River Trail Marathon is an annual running event held in West Virginia, featuring a full marathon (26.2 miles) and a half-marathon (13.1 miles). The marathon course is a scenic, point-to-point route that starts at Cass Scenic Railroad State Park and finishes at Stillwell Park in Marlin..