Trail Running calendar near Annapolis 2025-2026

Join the Sierra Club Lancaster Polar Bear 5K trail run and hike on January 10 for a chilly, scenic outing with some hills at Lancaster County Central Park. Chip timed and dog friendly, the event raises funds for local environmental grants.

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 rugged trails at Killens Pond State Park in Felton Delaware during the Angela Ivory Memorial Trail Runs on January 24 and 25 2026. Distances include a 50k, 100 Miler and 24 Hour event; 50k is currently full.

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..

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 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 scenic single track around Saint Marys Lake and Salem Forest with 17K, 34K, and 50K options on a 10.5 mile loop. Limited to 100 runners, the friendly trail race finishes with warm food and pancakes.

Take on the Hashawha Hills 50K in Westminster MD, a scenic trail run of two equal loops through woods, meadows and rolling farmland. Expect runnable single track, gravel sections and a few stream crossings for a varied, fun ultramarathon.

Hit the trails at the Bigfoot Endurance 5 and 10 Mile on March 1, 2026 at Rockburn Branch Park, with solo and relay entries on easy to moderate terrain. Entry includes a long sleeve shirt and finisher medal and benefits Parkinsons research.

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.

Take on scenic forest trails at Conway Robinson State Forest with a 5k or two lap 10k, suitable for runners and walkers of all levels. Support the Lost Dog & Cat Rescue Foundation and earn a finisher coin plus a tech shirt.

Join the scenic Seneca Creek Greenway Trail in Gaithersburg MD on March 7, 2026 for a marathon or an extended 50K. Run single track parkland trails and choose to finish at the marathon or keep going to complete the 50K.

Take on runnable hills, mud and possible snow on the Ranger Trail at Codorus State Park with 8 Miler, 25K or 50K loop options. Presented by York Road Runners Club, the race benefits a local animal rescue and offers prizes and swag.

Tackle the HAT Run 50K, a scenic and challenging trail race in Havre de Grace on March 21, 2026. Expect varied terrain, nearly 4,400 feet of climbing and a few stream crossings that keep the adventure real.

Join Washed Clean on March 28 at Genesis Church in York for a fun trail run or walk that finishes with a foam celebration and a free kids fun run. Family friendly and charity focused, register early for a free t shirt and water bottle.

Hit the scenic B&A Trail in Severna Park on March 29, 2026 with marathon and half marathon options, the marathon a Boston qualifier. Enjoy a mostly flat rails to trails route, generous aid, a finisher medal and participant apparel.