Trail Running calendar near Stuarts Draft 2025-2026

The Mountain Masochist Trail Run (MMTR) is a renowned ultramarathon held in Montebello, Virginia, featuring distances of 100K, 50 miles, and 50K. Celebrated as one of the best trail races in the Eastern U.S., the course starts and finishes at Montebello Campground, traversing scenic Blue Ridge Mount..

The Harvest Hustle 10k and 5k is a trail running event held at Walnut Creek Park near Charlottesville. The race features a challenging cross-country course with elevation changes, rocks, and roots, offering a scenic and adventurous experience for participants. Runners receive a finisher’s medal, a t..

The Lake Anna Turkey Trot Half is a scenic and challenging race held at Lake Anna State Park, featuring a half marathon, 10k, and 5k courses. The half marathon is an out-and-back trail race with a 3-hour and 15-minute time limit, while the 10k and 5k courses combine trail and paved roads. Participan..

The Freight Train 100k/50k is a winter ultramarathon held in Farmville, Virginia, featuring race options of 100 kilometers, 50 kilometers, a half marathon, and a half marathon hike. The course follows a relatively flat rail trail with less than 1,500 feet of elevation gain for the 100k, making it a..

The Freight Train Ultra Marathon is held at High Bridge Trail State Park in Farmville, Virginia. It offers three distances: a half marathon, 50k, and 100k, all on a flat rail trail with under 1000 feet of elevation gain. The course features scenic stretches including the iconic High Bridge, with aid..

The Tinsel Trot 10k in Louisa, VA, is a festive cross-country running event held at Southern Revere Cellars. The course loops around the winery property, with the 10k consisting of four laps and the 5k two laps, featuring gentle terrain without major hills. Participants receive a technical event shi..

The ICY-8 Spotsylvania Courthouse is an endurance trail running event held at Lake Anna State Park in Spotsylvania, Virginia. Featuring an 8-hour adventure trail run and a new half marathon+ option, the event offers a figure-8 course composed of three loops: an 8.0-mile long loop, a 4.7-mile loop, a..

The Holiday Lake 50K, held in Appomattox, Virginia, is a well-established ultra trail race founded in 1996. It features a scenic loop course around Holiday Lake, combining country roads and trails, making it ideal for first-time ultra runners as well as seasoned athletes. The event also includes 10K..

The RRRC Bear Creek 10 Mile Trail Run is a scenic trail race held at Bear Creek Lake State Park in Cumberland, Virginia, about 45 minutes west of Richmond. The event features a challenging 10-mile loop course through the piedmont hills of Cumberland State Forest and the state park, primarily on sing..

The Terrapin Mountain race, held in Sedalia, Virginia, is a popular spring trail running event featuring a 50k and a half-marathon. For over 17 years, it has attracted runners to the scenic and challenging trails around Terrapin Mountain, White Oak Ridge, Goff Mountain, and Hunting Creek. Participan..

The James River Trail Runs, held at James River State Park in Gladstone, Virginia, offer a variety of challenging trail race distances including a 10 miler, 50K, 50 mile relay, and 50 mile solo, with a new 10 mile night race added. The course consists of a 10-mile loop featuring rugged single and do..

The Massanutten Mountain Trails (MMT) 100 Mile Run is a challenging ultramarathon held in the Massanutten Mountains within Virginia’s Shenandoah Valley. Starting and finishing at Caroline Furnace Lutheran Camp in Fort Valley, VA, the rugged course features rocky trails and steep mountain climbs tota..

The Old Dominion 100 Endurance Run, held in Fort Valley, Virginia, is a challenging 100-mile race featuring a diverse course that includes pavement, gravel roads, single-track trails, ATV trails, logging roads, rocks, streams, and mud. This unique event tests runners' versatility across multiple ter..