Trail Running calendar near Annapolis 2025-2026

Enjoy a scenic 13.1 mile run along the C&O Canal Towpath at the Founders Half Marathon in Potomac, part of the DCRR Snowball Series. Friendly on course support and post race snacks make this a welcoming community event.

Join the Anniversary Run 15K at Quiet Waters Park, a scenic trail race that wraps up the Annapolis Striders Championship Series. Finish at Sassafras Pavilion for awards, a lively community vibe, and volunteer opportunities.

Celebrate the season at the Holiday 4 Miler in mid December at Lake Accotink Park in Springfield. Run a scenic loop on paved and dirt trails along the CCT, with in person and virtual options.

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.

Run the Bigfoot Endurance 5 Miler or 10 Miler at Rockburn Branch Park on March 1, 2026, with a relay option and scenic trail loops. Proceeds support Parkinson's research and entry includes a long sleeve shirt, medal and two post race beers.

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.

Run a flat, out and back 5k or 10k along Brunswick's scenic gravel path and support Wear Blue: Run to Remember. Finishers get a medal, technical shirt and a beer, with virtual options available for out of town runners.