Trail Running calendar near Charlottesville 2026-2027

Run the Bull Run Run 50 Miler on April 4, 2026 in Clifton Virginia, a 50 mile trail through rolling forest and spring bluebells along the Bull Run Occoquan Trail. Civil War themed course, riverside views and a 13 hour cutoff.

Enjoy a scenic three loop 5k through Molon Lave Winery in Warrenton on April 4, 2026. Walkers and virtual runners welcome and finishers receive a winery glass, medal and tech shirt for a festive post race celebration.

Relaxed 14 mile point to point run along the scenic Dahlgren Railroad Heritage Trail in Virginia with gentle elevation. Quirky aid stations serve pie, s'mores and pretzels and finishers receive practical swag while supporting local charitie..

Tackle the rugged Mineshaft 10k in Buchanan VA on April 4, 2026, featuring a scenic trail course with a steep climb, rocky sections and a flowing downhill finish. Limited to 100 runners with shuttle start and virtual option available.

The Happy Camper Trail Race will take place in Bedford on Saturday 4 April 2026. You can run between 5 and 10 kilometers.

Tackle rugged single and double track trails at James River State Park on April 11, 2026. Run 10 mile loops in 10 mile, 50k or 50 mile races with big climbs, river views and a 16 hour cutoff for an epic trail challenge.

Run through scenic vineyard trails at Southern Revere Cellars on April 18, 2026 with 5k and 10k options and a virtual race. Enjoy a postrace glass of wine or beer while supporting Hooves & Paws Animal Rescue.

Run scenic vineyard loops at Mountain & Vine in Faber with 3k, 6k or 9k over hilly terrain. Enjoy a finisher medal, tech shirt and a glass of wine while supporting the Nelson County volunteer fire department.

Run Fest at Panorama Farms is an inaugural spring trail festival on private farm trails near Charlottesville with a 4 mile, a family 1 mile and a 4 person relay. Enjoy an after party with local beer, food and music while supporting the UVA..

Run 3k or 6k through Barrel Oak Winery vineyards in Delaplane VA on April 19, 2026 for a rolling cross country experience. Enjoy a glass of wine, a medal and tech shirt while supporting Semper Fi and America's Fund; virtual and pet friendly..

Brave the winter trails of the Blue Ridge at Hellgate 100K++, a 66.6 mile mountain course in Natural Bridge Station, Virginia. Finish within 18 hours for a shot at the 2027 Western States lottery.

Join the Freight Train Ultra on May 9 in Farmville, VA for a half marathon, 50k or 100k along the scenic High Bridge Trail. Enjoy a fast, mostly flat rail trail, handcrafted finisher ornaments, pottery awards and support for crews and pacer..

Run 100 mile through the rocky Massanutten Mountains in Fort Valley, Virginia, tackling rugged climbs and trails. With a 36 hour cutoff and volunteer staffed aid stations, this classic ultramarathon tests endurance and grit.

Run a scenic, flat 5k along the Virginia Capital Trail by the James River at Rocketts Landing in Richmond. Choose in person or virtual entry, enjoy chip timing, a tech race shirt and finisher medal, with live results posted after the race.

Enjoy a scenic 5K on trails across a 100 acre organic farm by the Cacapon River in Wardensville. This family friendly fundraiser benefits local volunteer fire and rescue and the Youth Giving Committee, with food and leashed dogs welcome.

Celebrate Memorial Day with a 10K run or 2 Mile walk in Lynchburg, Virginia to support families affected by Type 1 and Type 2 diabetes. The chip timed 10K awards finisher medals and offers shirts for early registration.

Tackle 100 miles through the Massanutten Mountains and Shenandoah Valley from Fort Valley, Virginia. This scenic loop blends trails and road, climbs about 14,000 feet and serves as a true endurance test with a 24 hour silver buckle cutoff.

Tackle the OSS/CIA 50 Mile Night Run in Prince William Forest Park with 50, 25 or 10 mile options under the stars. Enjoy single track trails, stocked aid stations and a scenic loop run twice for the 50 mile.

Night Train returns June 20, 2026 in Farmville, Virginia for moonlit runs along the High Bridge Trail State Park. Choose 50K, half, 5K or a Family 5K and enjoy a flat rail trail, finisher awards and fireflies lighting the way.

Take on the High Bridge Challenge on June 20, 2026 and link two Virginia Adventures races along the scenic High Bridge Trail near Farmville. Choose a combo from 26k to 150k and earn a special award for completing both races.