Trail Running calendar near Montebello 2025-2026

The Conquer The Cove Marathon Trail Race, held annually at Sherwood Archers in Roanoke, Virginia, offers challenging 25k and marathon distances through Carvins Cove Natural Reserve, the second largest municipal park in the U.S. Covering approximately 12,700 acres with around 40 miles of trails, the..

The Old Dominion 100 Mile Endurance Run is a challenging ultramarathon held in Fort Valley, Virginia, featuring a measured loop course through the Massanutten Mountains and Shenandoah River Valley. The race covers 100 miles with 14 significant climbs totaling 14,000 feet of elevation gain. Participa..

The National Trails Day 5K in Rice, Virginia, is a celebration of outdoor activity and community spirit, taking place at High Bridge Trail State Park. This event features a scenic out-and-back course across the historic High Bridge, designed for both runners and walkers. Participants can enjoy the c..

The Night Train 50K and Half Marathon is an annual nighttime trail running event held at High Bridge Trail State Park in Farmville, Virginia. The race features three distances: a 50K, a half marathon, and a sunset 5K, all following a historic rail trail through scenic countryside and small towns. Th..

The Jackson River Scenic Trail Marathon, Half Marathon, 10k, and 5k is a vibrant running event taking place in Covington, Virginia. The USATF certified course starts and ends at the Intervale Trail Head, following a scenic route along the Jackson River. Participants can enjoy a smooth, mostly flat t..

The High Bridge Challenge in Farmville, Virginia, offers runners a unique opportunity to complete two races on the scenic High Bridge Trail State Park. Participants can choose from combo distances ranging from 26k to 150k, combining the Night Train race in June and the Freight Train race in December..

The 53rd Winery 5k & 10k is a scenic cross-country race held at 53rd Winery in Louisa, Virginia. Participants can choose between a 5k or 10k course, which loops around vineyards and winery grounds. The event features chip-timed races, finisher medals, technical shirts, and a complimentary glass of w..

The Jarmans Invitational Marathon, held annually in Crozet, Virginia, is a challenging 30-mile race featuring a grueling course with 7,610 feet of elevation gain and loss. Runners tackle a steep gravel road, Jarmans Gap, five times, each lap involving a 2.9-mile climb and descent. The course is know..

The Merrie Mill Farm & Vineyard 10k is a scenic cross-country race held at Merrie Mill Farm & Vineyard in Keswick, Virginia. The course features a mix of flat gravel, dirt, and paved roads with some notable hills, offering one lap for the 5k and two laps for the 10k. Walkers are welcome, and a virtu..

The Orchard Dash 10k is a cross-country trail race held at Albemarle CiderWorks in North Garden, Virginia. The event features both 5k and 10k routes, with the 10k consisting of two laps on a hilly course. Participants receive a finisher’s medal, a technical event shirt, and a glass of cider from Alb..

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 Vineyard Vista 10k and 5k is a scenic running event held at Muse Vineyards in Woodstock, VA. Participants can enjoy a course that combines cross-country around vineyards, paved road sections, and trail segments through Seven Bends State Park. The event benefits Friends of Seven Bends State Park..

The Grindstone Running Festival by UTMB is a premier trail running event held in Natural Chimneys Park, Virginia, just west of the Shenandoah Valley. Set amid the George Washington and Jefferson National Forests, the festival offers stunning fall foliage, mountain views, and challenging terrain. Run..

The Pawpaw 10 Miler and 5 Miler take place at Powhatan State Park in Powhatan, Virginia, celebrating the park's 10th anniversary alongside the annual Pawpaw Festival. The event offers a 10-mile race and a shorter 5-mile option, featuring scenic routes along the James River, open fields, shaded singl..

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 loops once around the winery property, including a mix of flat gravel, dirt, paved roads, and some notable hills. A 1-mile race option is also available.Participants rec..

The Rehab Rover Canicross and Trail Race is an exciting event taking place in Gordonsville, Virginia, featuring a 10K, 5K, a casual dog-friendly 5K, and a virtual 5K option. Scheduled for October 4, 2025, this race promotes the bond between participants and their dogs as they navigate scenic trails..

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..

The West Virginia Trilogy is a three-day trail running event held in the Monongahela National Forest, near Spruce Knob and Seneca Rocks National Recreation Area in Circleville, WV. Taking place over Columbus Day weekend, the Trilogy features a challenging series of races along the Eastern Continenta..

The Piedmont 8 Hour is a trail running event held at Powhatan State Park in Powhatan, Virginia. Celebrating its 10th year, the race features a 2.7-mile loop with about 60 feet of elevation change, winding through open meadows and pine forests with scenic fall foliage. The course is mostly runnable w..

The Into the Darkness Night Trail Run is a unique 4-mile race held in Explore Park, Roanoke Valley, featuring a mix of IMBA-designed trails and gravel roads. Participants navigate the course illuminated by reflective markers and glow sticks, making it a family-friendly event. A headlamp or flashligh..