Trail Running calendar near Frederick 2026-2027

Run the Muddy Shoes Farm Park Challenge at Agricultural History Farm Park on May 2, 2026, completing each lap in under one hour. Choose 3 hour, 6 hour, or 10 hour challenges or marathon and 25K; volunteers get event swag.

Run scenic singletrack along the Bull Run Occoquan Trail at the Fountainhead Half Marathon Plus and 10K Plus on May 3, 2026 in Fairfax Station, VA. In person and virtual entries benefit local charities for a rewarding spring trail challenge..

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

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.

Conestoga Crusher is a rugged trail run at Kelly's Run with creek crossings, steep climbs and the scenic Pinnacle Overlook. Choose 10K, 5K or the free RunPA kids Little Crusher and enjoy chip timing while supporting 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.

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.

Run scenic single track trails at the Blue Crab Bolt Trail Run at Seneca Creek State Park on June 27, 2026. Choose a 5K or 10K and enjoy woods, lake views and streams as the kick off to the Blue Crab Bolt series.

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.

A free Forrest Gump themed fun run on Lakeside Loop in Owings Mills offering a full 4.4 mile loop or a 1 mile out-and-back option, meeting at New Town Village Center with themed attire suggested.