Trail Running calendar near Frederick 2026-2027

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 timed trail event at Agricultural History Farm Park in Derwood, Maryland on May 2, 2026. Runners repeat a 5 mile out and back lap under one hour for 3, 6, or 10 hours; a marathon and 25K are also offered.

Trail races at Fountainhead Regional Park include an 11ish km 10K course and a 13.5 mile half marathon with multiple aid stations offering water and Gatorade. The event includes virtual options and supports the charity Homestretch.

Join the Johnnycake Jolt Series: four 10K trail runs in Patapsco Valley State Park's Pickall Area from May 6 to May 27, 2026. Enjoy scenic singletrack, official timing, and local festival vibes across four spring weekends.

The Historic Waterford Trail Run/Walk will take place in Waterford on Saturday 9 May 2026. You can run between 5 and 10 kilometers.

The Johnnycake Jolt Series will take place in Windsor Mill on Wednesday 13 May 2026. You can run between 10 and 40 kilometers.

A 100 mile trail ultramarathon in the Massanutten Mountains with rocky terrain, short steep climbs totaling over 18,000 feet of ascent and a 36 hour cutoff. The event features well stocked aid stations, marked trails and lodging options.

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.

Trail races at Kelly's Run Nature Preserve in Holtwood, PA on May 16, 2026 featuring 10K and 5K courses plus a free kids race. Events are chip timed, include aid stations, marked courses, and support the Lancaster Conservancy.

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.

The Johnnycake Jolt Series will take place in Windsor Mill on Wednesday 20 May 2026. You can run between 10 and 40 kilometers.

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.

The Johnnycake Jolt Series will take place in Windsor Mill on Wednesday 27 May 2026. You can run between 10 and 40 kilometers.

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 measured *100-mile* loop through the Massanutten Mountains and Shenandoah River Valley with varied terrain, 14,000 feet of gain and 14 climbs. The volunteer-run event offers a 24 hour cutoff for the silver buckle.

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.

The Awesum Possum Lake Trail Adventure will take place in Carlisle on Saturday 6 June 2026. You can run between 4 and 6 miles.

A night-focused trail event at Prince William Forest Park offering a 50 mile race plus 25 mile and 10 mile options. The 50 mile uses a 25+ mile loop run twice and features staffed aid stations and specific crew and pacer rules.