Trail Running calendar near Derwood 2025-2026

The Third Winchester Battlefield Half is a scenic running event held at Third Winchester Battlefield in Winchester, Virginia. It offers three race distances: 5k, 10k, and a half marathon, with the half marathon consisting of three loops on a mostly light gravel dirt trail featuring an out-and-back d..

The MD Heat Trail Race, held in Elkridge, Maryland at the Patapsco Pickall Area, offers challenging trail running options of 25K and 50K distances. The course features rolling single-track trails with over 2,000 feet of elevation gain, including technical rocky sections, two river crossings, and sce..

The Slopeside Slumber Party is a unique nighttime running event held at Roundtop Mountain Resort in Lewisberry, PA. Participants tackle a challenging ~1.5-mile loop featuring 600 feet of elevation gain, including a steep climb to York County's highest point and a thrilling, fully lit descent. The co..

The 2025 Gettysburg Brewfest & Trail 5K is a unique running event held in Gettysburg, Pennsylvania, at 890 Hanover Road. This 5K trail run combines fitness with fun, offering participants a race shirt (for early registrants) and a special event bottle opener medal. The race takes place near the hist..

The Miner's Lady 8 Hour Endurance Race is held in Harpers Ferry, West Virginia, where the Blue Ridge Mountains meet the Shenandoah River. This challenging event features an 8-hour timed run on a scenic 10K loop course with 850 feet of elevation gain. The trail includes crushed gravel, single track,..

The Tom LaMonica Memorial 5K Trail Run is held at the Genesee Valley Outdoor Learning Center in Parkton, Maryland. This challenging yet scenic 5K course winds through woods, trails, fields, and ponds on the center's 150-acre property. The event also features a 1-mile walk and team challenges for gro..

The ToM Opening Night VA is a cross country running event held at Morven Park in Leesburg, Virginia. Scheduled for late August, it serves as a kickoff to the high school cross country season. The event features a spectator-friendly course and includes an open race for friends and family, allowing pa..

The Inferno 10k is a challenging trail running event held at Dirt Farm Brewing in Bluemont, Virginia. The course features rugged forest terrain with technical sections including tree roots, rocks, and elevation changes, offering a demanding yet scenic experience. The 10k route is a loop run twice, w..

The Sasquatch Preservation Trail Run is a chip-timed 5K and 10K trail race held at South Branch Farms in Seven Valleys, Pennsylvania. Celebrating its 14th year, the event offers a scenic off-road course featuring varied terrain through farmland, woods, pastures, and streams, including a climb over t..

The Vineyard Vista 10k is a scenic running event held at Muse Vineyards in Woodstock, Virginia, along the North Fork of the Shenandoah River. The course features a mix of cross-country trails through vineyards, paved road sections, and trails around Seven Bends State Park. Runners can choose between..

Trails 4 Tails in Hanover, PA, is a trail running event held at scenic Codorus State Park, featuring a 5.72-mile loop course around Lake Marburg with single track trails and shoreline views. The event offers three race options: a 40 Mile Ultra (7 loops, ~4,200' elevation gain), a 40 Mile Relay (team..

The VHTRC Women's Half Marathon will take place in Fairfax Station on Saturday 13 September 2025. You can run between 7 and 13 miles.

The Tails on Trails 5K Run/Walk takes place at Cacapon State Park in Berkeley Springs, West Virginia. This early fall event features an easy 5K course along the Rock & Roll Trail, suitable for runners and walkers of all levels. The scenic trail highlights the natural beauty of the area, making it a..

The All Hollowed Out 5K is a race held in Carlisle, Pennsylvania, at 500 Kings Gap Road. Sponsored by the Friends of Kings Gap, the event supports the refurbishment of the carriage house at the historic Cameron Masland Mansion and other projects in the area. The course features a mix of terrain, wit..

The 12 Hour Adventure Trail Run, held at Prince William Forest Park near Triangle, VA, is an endurance trail running event featuring a 6.5-mile figure-eight loop course. The course, set on 100% trails including single track and fire roads, offers approximately 650 feet of elevation gain per loop wit..

The Valley View Hard Cider Challenge Half is a scenic and challenging running event held at Valley View Farm in Delaplane, Virginia. The race features a half marathon, 10k, and 5k distances, with courses combining cross country, trail, and hilly terrain. The half marathon is an out-and-back route co..

The Cancer Warriors 5k is an annual fundraising event held in Baltimore, MD, with the 9th edition scheduled for September 20, 2025. The race takes place on the scenic Ma & Pa Trail in Belair, featuring a straightforward out-and-back course that crosses streams and passes under Route 24, ending near..

The Final Countdown Tribute is a unique running event held at Amani Brewing in Martinsburg, WV. The race features a 1.33-mile loop on a smooth, well-maintained grass trail with gentle hills. Runners must complete each lap within a decreasing time limit, starting at 20 minutes and shortening by 20 se..

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 Laurel Ridge Community College 5K is a multi-surface, cross-country run/walk event held on the Middletown campus of Laurel Ridge Community College. The race starts and finishes outside the Student Union Building on Garland Snapp Drive. The course includes running in front of the school, a shorte..