Trail Running calendar near Winchester 2025-2026

Rosaryville Veterans Day Trail Race, held in Rosaryville State Park in Upper Marlboro, Maryland, offers 50K and 20K trail distances on wooded perimeter single-track trails. The course features rolling hills with about 2,600 feet of elevation gain, mostly through deep woods and meadows, with scenic v..

The Barrel Oak Turkey Trot is a pre-Thanksgiving running event held at Barrel Oak Winery in Delaplane, Virginia. It features two race distances: a 3k and a 6k, with the 6k consisting of two laps around a cross-country course that winds through vineyards, gravel roads, and hilly terrain. The event we..

Fall Backyard Burn at Hemlock Overlook is part of EX2 Adventures’ Fall Backyard Burn Trail Running Series. Held at Hemlock Overlook, Clifton, Virginia, the event offers 5-mile and 10-mile trail courses. Elevation gains are about 600 feet for the 5M and 1,200 feet for the 10M.The courses traverse Bul..

Freeze Your Gizzard 5K and 1 Mile is held at Ida Lee Park in Leesburg, Virginia. Celebrating 23 years of running, this cross-country event offers a 5K through Ida Lee Park’s 138 acres and a 1-Mile Fun Run, starting and finishing near the park’s Gazebo. The course features uneven terrain and steep hi..

Fall Backyard Burn at Laurel Hill Park in Lorton, Virginia, takes runners through 1,600 acres of the former Lorton Reformatory grounds. The course starts and finishes under the old guard towers at the Workhouse Arts Center, winding mostly on forested and open meadow singletrack of dirt and crushed s..

The Winery at Bull Run Turkey Trot offers a scenic trail 5k and 10k through the Manassas National Battlefield Park, starting and finishing near The Winery at Bull Run in Centreville, VA. The course is a cross-country style route across battlefield trails, including dirt paths, a boardwalk, and grave..

The 21st Annual Catonsville High School XC Turkey Trot, held in Catonsville, Maryland, is a cherished community event celebrating health, wellness, and family. It features a cross country-style 1 Mile Family Fun Run and a 5K race, both chip timed. The event fosters a spirited atmosphere with awards..

The Lake Anna Turkey Trot Half is a scenic and challenging running event held at Lake Anna State Park in Spotsylvania, Virginia. It features three race distances: a 5k trail run, a 10k that is half trail and half paved road, and a half marathon with a similar mixed course. Walkers are welcome, and t..

Devil Dog Ultras is a trail ultramarathon in Prince William Forest Park, VA. It offers 100-mile, 100K, and 50K loops on trails with roots and rocks, plus fire roads. The first loop is 23 miles; subsequent loops are 19.5 miles.The 50K is one loop plus a 9-mile extension; the 100M runs five loops and..

Fall Backyard Burn Trail Run - Fountainhead is a trail-running event at Fountainhead Regional Park in Fairfax Station, VA. The race offers two distances: a 5-mile loop and a 10.5-mile course, with elevation gains around 450 feet and 1000 feet, respectively. The 5-mile loop is a classic EX2 single lo..

Located at Rockburn Branch Park in Elkridge, Maryland, the Mid-Maryland Trail Festival 50k is a 31-mile ultramarathon built from six loops of about 5.18 miles through wooded trail terrain. The event also offers a 50k relay, allowing teams of up to six runners to share the distance with exchanges aft..

Froggy Hollow 5 & 9 presented by Altra is a Charm City Run signature trail ultra held at Little Bennett Campground in Clarksburg, Maryland, inside Little Bennett Regional Park. The event includes 5-Hour Challenge, 5-Hour Relay, 9-Hour Challenge, 9-Hour Relay, and More Than a 4-Miler, all based on a..

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

Paradise Springs 5k & 10k is a trail race at Paradise Springs Winery in Clifton, VA, offering a technical Hemlock Overlook Park course by the river. The 10k is two laps of the 5k route, with substantial elevation changes and a rocky section. Runners receive a finisher medal, technical shirt, a glass..

The Winter Conway Robinson 10k is a trail running event held at Conway Robinson State Forest Park in Gainesville, Virginia. The race features a scenic loop course through forest trails with some technical terrain and minor hills, with the 10k consisting of two laps of the 5k route. Walkers are welco..

No Man's 50K is a women-only trail running endurance event held in Triangle, Virginia, featuring 25K and 50K distances. The course consists of two loops of approximately 15 miles each, designed as a great first-time ultramarathon route. Runners experience a mix of terrain with about 70% single track..

The Dark Side 8 Hour Ultra is an eight-hour trail race at Little Bennett Park in Montgomery County, Maryland, near Clarksburg. The course is a 5.5-mile loop run mostly on single-track trails, starting at the Little Bennett Campground Pavilion. Runners may complete as many laps as they wish within th..

The Twisted Oak 8k is a cross-country running event held at Twisted Oak Farm Brewery in White Post, Virginia. The course features scenic views around the brewery property with minimal hills, where the 8k race consists of two laps. Participants enjoy a challenging yet beautiful run and receive a fini..

Capital Backyard Ultra is a Last Runner Standing race held at Meadowood Special Recreation Management Area, 10702 Harley Rd., Lorton, Virginia, near Washington, DC. The course is a 4.167-mile loop that runners complete in succession, with the field reduced until only one remains, who must finish one..

Bull Run Run 50 Miler is a 50-mile trail race held in Clifton, Virginia, at Hemlock Overlook Regional Park. The course runs through forested, rolling terrain generally paralleling the Occoquan River and Bull Run during Virginia’s spring bloom. A Civil War theme honors battles that occurred in the ar..