Trail Running calendar near Delaplane 2026-2027

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.

This 5k offers a scenic cross-country loop around the Bluemont Station Brewery & Winery property. Runners receive a technical shirt, finisher medal, and a post-race beverage. The event supports the I AM ALS charity and features a virtual pa..

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.

Perfect Day 50K in Massanutten is a 50 kilometer event on May 2, 2026, at Massanutten Western Slope near Keezletown, Virginia. It offers individual entries and team options for two or three people with a listed price of $99 per person.

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.

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.

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.

Race through history on the trails of Manassas National Battlefield at dusk. The Night Raider offers 5k and 10k distances starting and finishing at the Winery at Bull Run. Runners receive a medal, tech shirt, and a post race 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 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.

Run a scenic but technical loop trail at Sky Meadows. The event features a 5k and 10k, with finisher medals and chip timing. Points count towards multiple race series, and walkers are welcome.

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.

A 45th annual five-mile out-and-back on the C&O Canal Towpath in Williamsport, MD, on June 6, 2026. Chip timing, a technical race shirt, and age-group and overall awards are part of the event.