Trail Running calendar near Montebello 2025-2026

Grindstone Running Festival by UTMB is a trail ultramarathon event held at Natural Chimneys Park near the Shenandoah Valley in Virginia. The festival offers four distances—100M, 100K, 50K, and 21K—tracing routes through the George Washington and Jefferson National Forest with steep climbs, ridges, v..

Pawpaw 10 Miler and 5 Miler take place at Powhatan State Park in Powhatan, Virginia, pairing a park-centered trail race with the Pawpaw Festival. The events offer a 10-mile main course and a 5-mile option (plus hiker variants) that wind along the James River: riverfront flats, open fields, and shady..

The Woodstock Warrior is a challenging trail running event held at Seven Bends State Park in Woodstock, Virginia. It features a roughly 10-mile loop course with mixed terrain including gravel roads, two-track dirt roads, and single-track trails, with about 1800 feet of elevation gain per loop. The r..

The Nasty 9 Trail Run takes place in Lexington, Virginia, within the scenic 600-acre Brushy Hills watershed in the Shenandoah Valley. This competitive trail race offers two distances: a challenging 9-mile course featuring over 2,000 feet of vertical gain, and a shorter 3-4 mile course with about 500..

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 includes a mix of flat gravel, dirt, paved roads, and some notable hills, offering a varied terrain for runners. Participants also have the option to run a 1-mile distan..

Set along the scenic Greenbrier River Trail in Pocahontas County, West Virginia, the Greenbrier River Trail Marathon and its companion half-marathon offer a flat, fast, rail-trail experience. The 26.2-mile marathon is a point-to-point race starting at Cass Scenic Railroad State Park and finishing at..

The West Virginia Trilogy is a three-day stage race on and around Spruce Knob, on the Eastern Continental Divide. It takes place over Columbus Day weekend, October 10–12, 2025, and is hosted by the West Virginia Mountain Trail Runners with race headquarters at the Spruce Knob Mountain Center’s 400-..

Piedmont 8 Hour takes place at Powhatan State Park in Powhatan, Virginia. The event offers an 8-hour format with 2.7-mile loops, each gaining about 60 feet of elevation. The course blends open meadow running with pine forests, delivering scenic fall foliage and plenty of birdlife.Runners receive aid..

The Deep Hollow Half Marathon & 5K Trail Race takes place at Hydaway Outdoor Center in Lynchburg, Virginia. It offers a Half Marathon (13.1 miles) on primarily single-track trail with some forest roads, and a 5K (3.1 miles) out-and-back on a forest road. The event is the premier trail race in the Li..

The Bivanna Trail Extravaganza is a trail running event held in Charlottesville, Virginia, featuring multiple race distances on the scenic Rivanna Trail. Participants can choose from a 40-mile full loop, a 20-mile half loop (Demibivanna), a 10-mile quarter loop (Hemidemibivanna), or a 40-mile biking..

The Heart of Virginia Council Glow Trail Run 5K is a unique nighttime trail running event held at Camp Brady Saunders in Maidens, Virginia. This family-friendly race welcomes participants of all ages and is open to everyone, not just Scouts. The course features a 5K trail illuminated with glow-in-th..

Andy’s Backyard Ultra is a last-person-standing ultramarathon held at Teventrails in Earlysville, Virginia, about 14 miles northwest of Charlottesville. The event uses the Backyard Ultra format: competitors must complete a 4.17-mile lap within one hour, and laps continue hourly until only one runner..

Run the Chessie is a USATF-sanctioned trail running festival in Lexington, Virginia, with events on the Chessie Nature Trail along the Maury River. The lineup includes a marathon, half marathon, 10K, 5K, and a 26.2 Relay. The trail is a smooth gravel-grass surface with gentle grades, running entirel..

Into the Darkness Night Trail Run is the Roanoke Valley’s night-time trail race, returning for its 19th edition on October 25, 2025. The event starts and finishes at Explore Park, Roanoke, VA, with a new course this year. Runners cover about 3.6 miles, beginning with a 0.25-mile asphalt section befo..

The Crozet Trails Crew 5K/10K Trail Run + Family Fun Run is a fundraiser in Crozet, Virginia hosted by the Crozet Trails Crew. The course starts and ends at Crozet Park, following rustic trails east of the park with roots, rocks, and ruts. Distances include Trail 5K, Trail 10K, and a Family Fun Run;..

Shenandoah Zombie Run is a 5K running event held at Camp Shenandoah in Swoope, Virginia. The course weaves through Camp Shenandoah’s hills and woods along Little North Mountain, offering forest trails as runners dodge zombies. Each participant wears a belt with three flags, representing lives to pro..

Mountain Masochist Trail Run is a long-standing mountain ultratrail in Montebello, Virginia, offering 100K, 50M, and 50K distances. The course begins and ends at Montebello Campground and, in recent iterations, is run in reverse toward the Mount Pleasant Loop, using a mix of old and new trails. Runn..

Ultra Race Of Champions is a mountain trail event held at Sherando Lake Recreation Area in the Blue Ridge Mountains of Virginia. Runners can choose from 40 miles, 20 miles, or 10 miles, with all races starting and finishing at the same venue. The course features dirt, single-track trails and jeep ro..

GEER, the Great Eastern Endurance Run, returns after a 15-year hiatus to Sherando Lake in Lyndhurst, Virginia, offering 40-, 20-, and 10-mile options. The course unfolds in the Blue Ridge mountains with predominantly single-track trails and remote forest roads, featuring climbs to Bald Mountain, rug..

Harvest Hustle 10k at Walnut Creek Park in North Garden, VA, offers a cross-country trail race with a 5k option as well. The course weaves through park woods with elevation changes, rocks and roots. The 10k features three water stations at roughly miles 2.1, 3.1, and 5.2; the 5k has a water stop at..