Trail Running calendar near Derwood 2025-2026

The ToM Opening Night VA is a cross-country kickoff hosted by Trials of Miles at Morven Park in Leesburg, Virginia. The event features a 5K cross-country race, with an open race for friends and family priced at $20. It’s designed to be spectator-friendly, offering a festival-like atmosphere on cours..

The High Rock Mountain Running Challenge is a Cascade, Maryland race starting and finishing at Pen Mar Park (14600 Pen Mar Rd). The course covers about 3.8 miles, including roughly 1.8 miles of ascent to High Rock Overlook before a descent back to the park for the finish. The route offers a pictures..

The Inferno 5k & 10k at Dirt Farm Brewing in Bluemont, Virginia, challenges runners with a forest-trail course behind the brewery. The 5k is a single loop; the 10k doubles back on the same path, featuring tree roots, rocks, and elevation changes that test footing and lungs. Expect steep climbs, rapi..

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..

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..

Vineyard Vista 5k & 10k takes place at Muse Vineyards in Woodstock, Virginia. The course blends vineyard cross‑country with a paved road segment and trail loop around Seven Bends State Park; the 5k is a single loop and the 10k uses two loops. The event offers a winery atmosphere, with participants e..

Athletic Equation will host its 18th Annual 12-Hour Adventure Trail Run at Prince William Forest Park, a 17,000+ acre, 40-mile trail reserve near Triangle, VA. The event covers 30 kilometers on a 6.5-mile looped figure-eight trail course, run for up to 12 hours with a two-person relay. The 100% trai..

The Creation House 5K Rugged Trail Run is a 5K trail race held in Littlestown, Pennsylvania (165 Christ Church Rd). It supports Creation House, a program designed to keep homeless families together as they rebuild their lives. The course is described as a beautiful, rugged nature run through farmlan..

Valley View Hard Cider Challenge Half, hosted by Bishops Events, takes place at Valley View Farm in Delaplane, Virginia. The event offers 5k, 10k, and Half-Marathon distances on knotty courses that blend cross-country, trail, and hills. The 5k and 10k are out-and-back once, while the Half is out-and..

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 Bull Run Reunion Run 2025 is a 3-mile cross country race held in Parkton, Maryland, at Hereford High School. Scheduled for September 20, 2025, this event is part of the Bull Run Cross Country Invitational and is open to all ages. The Reunion Run is the seventh race of the day, offering participa..

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 Cancer Warriors 5k is held in Belair, Maryland, on the Ma & Pa Trail. The in-person event features a simple out-and-back 5k course starting at the Ma & Pa Trail Head near Independent Brewery, with a second stream crossing, a fork near Route 24, and a turnaround near Tollgate Road before returnin..

Laural Ridge Community College 5K is a multi-surface cross-country style race/walk held on the Middletown Campus in Middletown, Virginia. The start and finish are outside the Student Union Building on Garland Snapp Drive. The 5K course includes a shorter lap around the back fields, a second lap arou..

9K for Semper K9 is a community running and walking event in Fredericksburg, Virginia, held at Old Mill Park along Canal Path by the Rappahannock River. The program includes a 9K race and a Kids .9 Mile Fun Run, welcoming runners, walkers, families. The course runs along canal paths in downtown Fred..

St. Anselm's Family 5k is a family-friendly fundraising race in Washington, DC, held at 4501 South Dakota Ave NE. The event covers a 5k distance on a double-loop trail course, suitable for runners and walkers alike.It benefits a memorial scholarship fund at St. Anselm's Abbey School, supporting stud..

The Kellie Thompson Shiley 5k and Family Fun Run is an annual event held at the Terrapin Nature Trail in Stevensville, Maryland, on the scenic Eastern Shore. It features a 5K trail run/walk and a 1-mile fun run for children aged 10 and under. The race honors Kellie Thompson Shiley’s competitive spir..