Trail Running calendar near Amissville 2026-2027

Run the scenic Third Winchester Battlefield on April 25 with 5K, 10K and half marathon options plus a virtual race. Enjoy chip timing, a finisher medal and tech shirt while supporting Team Virginia and organ transplant awareness.

Run three scenic laps around Bluemont Station Brewery & Winery in Bluemont, VA on April 26, 2026, and enjoy chip timing, a finisher medal, shirt, and a complimentary beer or wine. Walkers and virtual runners welcome.

A 5K trail run and walk on private property near Amissville, Virginia, benefiting the Chefs For Kids Foundation. The mostly dirt course has gentle hills; registration includes a race T-shirt, bib, and post-race refreshments.

A trail running event at Agricultural History Farm Park in Derwood, Maryland, featuring timed lap challenges where each lap must finish in under an hour and also offering a marathon and 25K.

Trail races at Fountainhead Regional Park near Washington DC offer an 11ish kilometer route and a 13.5ish mile half marathon over rocky, rooty trails with streams and steep climbs. Multiple aid stations provide water and Gatorade.

Run 100 mile through the rocky Massanutten Mountains in Fort Valley, Virginia, tackling rugged climbs and trails. With a 36 hour cutoff and volunteer staffed aid stations, this classic ultramarathon tests endurance and grit.

Run scenic out and back courses along the C&O Canal towpath in Potomac on May 16, 2026, with 5k, 10k and half marathon distances. Enjoy chip timing, a tech shirt and finisher coin, support the EOD Warrior Foundation, or take part virtually.

Supported hikes on the C&O Canal and the Appalachian Trail raise funds for Micah's Backpack and the Refugee Welcome Network. Options include 5K, 10K and longer challenge distances with route support and a post hike lunch.

Join the Night Raider at the Winery at Bull Run on May 22, 2026 for a festive evening 5k or 10k through scenic Manassas Battlefield trails. Enjoy chip timed results, a finisher medal, a technical shirt and a complimentary glass of wine.

Enjoy a scenic 5K on trails across a 100 acre organic farm by the Cacapon River in Wardensville. This family friendly fundraiser benefits local volunteer fire and rescue and the Youth Giving Committee, with food and leashed dogs welcome.

A May fundraising series on the C&O Canal and Appalachian Trail supporting HARC programs, with distances from 5K to a 20-mile challenge, on-trail support, and a post-hike celebration lunch.

A non competitive, fully supported hike on the C&O Canal towpath with 5 K and 10 K options, snacks and a post-walk lunch. Prizes recognize top fundraisers and fundraising participants enter a prize drawing.

Tackle 100 miles through the Massanutten Mountains and Shenandoah Valley from Fort Valley, Virginia. This scenic loop blends trails and road, climbs about 14,000 feet and serves as a true endurance test with a 24 hour silver buckle cutoff.

Run a flat, fast five mile out and back along the shaded C&O Canal Towpath in Williamsport, MD on June 6, 2026. Enjoy chip timing, tech shirt options and age group awards in a friendly community race.

Tackle the OSS/CIA 50 Mile Night Run in Prince William Forest Park with 50, 25 or 10 mile options under the stars. Enjoy single track trails, stocked aid stations and a scenic loop run twice for the 50 mile.

A chip-timed 5k at Corteau Vineyards on June 13, 2026, featuring a two-lap cross-country style course through the vineyards, age-group awards, race swag and a wine pour. Virtual participation and packet shipping are available.

Trail 5K and 10K at Seneca Creek State Park in Gaithersburg, MD featuring singletrack trails, lake views, aid stations, post race food, and a charity partner Interfaith Works.

Get muddy and fast at MCRRC XC on the Farm, a fun 5k cross country at Agricultural History Farm Park in Derwood on June 28, 2026. Open to all ages with affordable registration and a relaxed club atmosphere.

Run through rolling vines at 868 Estate Vineyards in Hillsboro with a scenic but hilly 5k or 10k course that tests and rewards. Finishers get a medal, tech shirt and a glass of vineyard wine, and a virtual option is available.

Trail races at Schaeffer Farms on July 25, 2026 offer a 5K and a longer 10K++ course that begin and end at Button Farm Living History Center. Courses feature single-track, stream crossings, log ramps and some rocky, rooty sections.