Trail Running calendar near Gordonsville 2026-2027

Tackle the historic Old Dominion 100, a classic ultramarathon loop through Virginia's Massanutten Mountains. The challenging course mixes roads and trails with 14,000 feet of climbing. Earn a silver buckle by finishing within 24 hours in th..

Celebrate National Trails Day on a flat, scenic 5k course across the historic High Bridge. This event welcomes runners and walkers, with all proceeds supporting park programs. Every participant gets a hat, finishers earn a medal, and local..

Run through history on the secret training trails of the CIA's predecessor in Prince William Forest Park. This night event features a 50-mile, two-loop course with a 14.5-hour limit, or a single 25-mile option. Pacers are allowed for the se..

Event Overview The Fauquier Education Farm 5K and Fun Run is a fundraising event for the Fauquier Education Farm, a 501(c)(3) organization. The organization's mission is to advance agriculture through education and best practice farming. It..

A Backyard Ultra in Midlothian on June 13 and 14, 2026, with repeating 4.167 mile loops every hour. Proceeds support the Semper Fi Fund; the last runner standing wins cash and the Sword of Honor.

Run under the stars on an historic rail trail at High Bridge Trail State Park. Choose from a 50K, half marathon, or 5K, with hiker-friendly and new family options available. Prepare for a hot, cupless race where carrying water is mandatory.

Event Information The High Bridge Challenge involves completing a combination of distances from two separate running events: the Freight Train in May and the Night Train in June. Both events take place on the High Bridge Trail in High Bridg..

Experience a mud run featuring obstacles and trails in King George Virginia. With four mile and one mile options plus team challenges this event supports local community eye and hearing care services.

Experience the West Side Quarry trail race along the Rappahannock River in Fredericksburg. This 10k course features a steady climb and rolling hills with 426 feet of elevation gain for a dynamic running experience.

Experience a scenic run through the 868 Estate Vineyards in Purcellville. Choose between 5k and 10k distances or participate virtually for an afternoon of outdoor activity at a Virginia vineyard.

The Jarmans Invitational Marathon will take place in Crozet on Saturday 1 August 2026. You can run between 29 and 30 miles.

Experience a scenic out and back race on the mostly flat Dahlgren Railroad Heritage Trail. Choose between a half marathon or 50K distance and enjoy a well supported course featuring finishers medals and cash prizes.

Experience the scenic and historical landscape of Winchester Virginia with a 5k, 10k, or Half Marathon at Third Winchester Battlefield. Both runners and walkers are welcome to participate in person or virtually.

Experience the Leopold’s Preserve 5k and 10k in Broad Run Virginia. This Sippin Series event welcomes both runners and walkers for a scenic race through the preserve in collaboration with the Farm Brewery at Broad Run.

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.

Conquer rugged terrain and steep inclines at Dirt Farm Brewing in Bluemont. Choose between 5k and 10k distances through breathtaking landscapes and enjoy a post race beer at the finish line.

Experience a cross-country run through the scenic grounds of Albemarle CiderWorks in Virginia. Choose between 5k and 10k distances or participate virtually followed by post-race cider at the orchard.

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.

Run through the beautiful Fifty-Third Winery & Vineyard in Louisa, Virginia. This 5k and 10k event supports animal rescue and sanctuary efforts for local wildlife and farm animals.

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.