Trail Running calendar near Leonardtown 2025-2026

Kick off the New Year with a no frills 5K or 8K along the Capital Trail in Williamsburg. Low cost entry supports CRR scholarship funds and the friendly post race vibe includes coffee and doughnuts.

Tackle a scenic 10 mile trail run at York River State Park featuring technical single track, fire roads and a downhill finish. Proceeds benefit AWARE and you can meet owls onsite while enjoying coffee and snacks after the run.

Run scenic trails at Harwoods Mill Park in Yorktown, VA on January 17, 2026 with a Half Marathon or 5K option. Limited fields, aid stations, and post race shirts make this a chilly January favorite for trail lovers.

Run scenic trails at Leesylvania State Park on January 17, 2026 and support Food for Others with 5k and 10k distances. Enjoy a mixed trail and pavement course, in person or virtually, with finisher medal and tech shirt for early registrants..

Take on scenic trails at Killens Pond State Park in Felton Delaware with the Angela Ivory Memorial Trail Runs, offering 100 mile, 50k and 24 hour race options. A communal, challenging winter weekend where some distances fill quickly.

Challenge yourself on scenic singletrack at Rockburn Branch Park in the Mid Maryland Trail Festival, featuring a 50K and a 50K relay. Run six loops or join a team of 2 to 6 with options to run fewer loops and aid stations on course.

Take on a fast, flat half marathon along the Dahlgren Railroad Heritage Trail in King George, Virginia on January 31, 2026. All finishers earn a custom medal and the race supports Friends of the Dahlgren Railroad Heritage Trail.

Run scenic, tame trails along the Little and Middle Patuxent Rivers in Columbia, MD during a fun January race weekend. Choose 5K, 10K or half marathon distances and earn finisher medals, a long sleeve shirt and knit gloves.

Brave wooded trails at Prince William Forest Park on Feb 1, 2026 with distances from 5k to 50k, featuring technical hills, roots and scenic views. Support Semper K9 and earn medals, tech shirts and chip timing in this winter trail challenge..

The Delmarva Ultra Challenge is a 100K trail test in Pocomoke run as two 50K efforts, one night and one morning. A surprise night course and limited spots make this a gritty, tactical event for experienced ultrarunners.

Join the 18th annual ICY 8 at scenic Lake Anna State Park on Feb 7 for 8 hour adventure trail runs, a Half Marathon Plus in a figure 8 format, or a challenging 8 miler. Mostly single and double track trails promise a fun, rugged day outdoor..

Community driven 50K trail race through Pocomoke River State Park, featuring mostly flat single track and scenic river views. Volunteer run with stocked aid stations and a handmade ceramic mug for every finisher.

Test your limits on this timed trail ultra at Little Bennett Campground with 5 and 9 hour solo and relay options on a scenic 4.4 mile loop. Enjoy aid stations, Altra demos and a post race chili while supporting Montgomery Parks Foundation.

Run a scenic trail 5k or 10k at The Winery at Bull Run with chip timed results, a finisher medal, tech shirt and a complimentary glass of wine. Proceeds support the Manassas Battlefield Trust.

Run a hilly trail 5k or 10k at Wilderness Run in Spotsylvania VA on Feb 14, 2026 and support Semper Fi and America's Fund. Chip timing, finisher medal, tech shirt and a post race beer or wine; virtual option available.

Run a scenic 5K through forest trails at Wicomico Demonstration Forest in Parsonsburg, MD on February 21, 2026. Proceeds benefit 4STEPS therapeutic riding programs, making this debut trail race a great way to support riders and enjoy nature..

Take on scenic river trails at the Paradise Springs 5k and 10k in Clifton VA on February 28, 2026, featuring challenging rocky sections and plenty of elevation. Finish at Paradise Springs Winery with a finisher medal, tech shirt and a compl..

Run a scenic 10.5 mile loop around Saint Marys Lake and into Salem Forest in Leonardtown, MD with 17K, 34K, and 50K options. Enjoy mostly single track trails, a field limited to 100 runners, and pancakes at the finish.

Join the Bigfoot Endurance Trail Race at Rockburn Branch Park in Elkridge on March 1, 2026 with 5 mile, 10 mile and two person relay options on scenic trails. Get a long sleeve shirt, finisher medal, post race beers and support Parkinson's..

No Man's 50K is a women only trail running challenge in Triangle, VA with 50K and 25K on scenic single track and forest roads. Two loop courses, full aid stations, and a welcoming vibe make this a must for endurance runners.