Trail Running calendar near Mount Airy 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.

The Run the Rock | Leesburg will take place in Ashburn on Saturday 25 April 2026. You can run 5 kilometers.

An annual 5K at Marymount University on April 25, 2026, run on the Bluemont and Custis Trails with a post-race gathering, a virtual option, chip timing, and guaranteed shirts for early registrants.

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.

A multi distance trail event in Waterford VA on May 9, 2026 that runs through historic village streets, vineyards, trails and unpaved roads. Proceeds support the Waterford Foundation and 5K and 10K finishers receive a shirt and medal.

A trail event at Cromwell Valley Park on May 9, 2026 featuring 25k, 12.5k and 5k courses. The event supports local conservation groups and includes family activities and an Explore Passport for young participants.

The Johnnycake Jolt Series will take place in Milford 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.

A spring road-and-trail event at Carderock Recreation Area with 5k, 10k and half-marathon out-and-back routes on the C&O Canal towpath, chip timing, finisher's coin, technical shirt, water stations, and a virtual option.

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 Milford 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.

The Johnnycake Jolt Series will take place in Milford 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.

The Crooked Run Valley 10k will take place in Delaplane on Sunday 31 May 2026. You can run between 5 and 10 kilometers.