Trail Running calendar near Annapolis 2026-2027

Teams and community meet at Burke Lake Park on June 6 2026 for a chip timed 5k run and a noncompetitive 2k fun walk, with awards, post-race food, and music.

Trail Trotters 5k & Fun Run is a community trail event at Promise Landing Farm in Upper Marlboro on June 7, 2026. The event features a 5k and a fun run; adult registration includes a T shirt and concessions with live music.

A night trail event in Prince William Forest Park offering a 50+ mile race made of two laps of a 25+ mile loop, plus 25M and 10M options. Aid stations are placed on course and crews are restricted to the Telegraph Road Pavilion.

A chip timed 5k at Corteau Vineyards in Mechanicsville, Maryland on June 13, 2026, featuring vineyard scenery, a t-shirt, collapsible wine glass, finisher medal that doubles as a wine stopper, and an on-site wine pour.

A community 5K and 1 mile Fun Run in Warrenton, VA that raises funds for Fauquier Education Farm, a 501(c)(3) that advances agricultural education and donates its harvest to local food banks.

A 5K road race in Dewey Beach on June 14, 2026 that benefits the Dewey Beach Patrol and is part of the Ten Sisters series. The event includes a competitive walking category, chip timing, tech shirts, and a post race party with food and beer..

A self-timed 4 miles run in Bel Air as part of the Harford County Running Club Dog Days of Summer Series. The course mixes trail and road, is not stroller friendly, and parking is at Prospect Mill Park.

A Juneteenth trail event in Germantown on June 19, 2026 offering 6K and 12K distances plus virtual options, with a hilly course around Button Farm and the Schaeffer Farm Trails and welcome to walkers.

A night trail relay in Paradise, PA where teams and solo runners try to complete as many loops as possible in about 3 hours and 24 minutes on a marked 2 mile course. Team batons, glow rings, headlamps and on site divisions are used.

A rugged out-and-back trail race near Frederick, MD, offering a 50K and a 25K Half Cat on rocky, shaded singletrack with stream crossings, three aid stations, and mandatory on-course hydration.

A 5 km and 10 km event along the Chesapeake and Ohio Canal path in Georgetown, Washington, DC on June 20, 2026. Walkers are welcome and registration fees vary by date with separate pricing for each distance.

A noncompetitive summer trail series in Lancaster County with three morning gatherings and one evening close. Participants pick their own distance, share breakfast and hydration at a Common tent, and may buy single-event or multi-event pass..

Experience a scenic 5 mile trail run through Lancaster County Central Park featuring grass paths and water crossings. Compete for age group awards and enjoy a post race prize raffle in a beautiful natural setting.

A free night training run in Salisbury, MD offering six hours of repeated 5K loops on marked trails. Space is limited to 50 runners and participants must provide their own hydration and fuel.

Kick off the Blue Crab Bolt series at Seneca Creek State Park with scenic 5K and 10K trail runs featuring lake views and singletrack paths. Enjoy professional race support, post-run breakfast burritos, and a festive atmosphere.

A mud-run fundraiser in King George, VA on June 27, 2026, featuring a 4-mile obstacle course and a 1-mile kids run, organized by the Dahlgren Lions Club with team awards by group size.

Trail runs at Rocky Ridge County Park on June 27, 2026 offering 50K, 33.3K, 16.7K and 10K on rocky, rolling trails with repeated loops. Registration deadlines apply and proceeds support a local charity.

MCRRC Cross Country on the Farm Trail 5K is a trail race at Agricultural History Farm Park in Derwood MD. Non member registration is available for a $20 fee and the event is part of the club's low key race series.

A free 5K fun run on July 4, 2026 organized by Great Falls TrailBlazers. The loop course goes through the woods, meets at the Great Falls Library, is open to all ages and is pet friendly.

A themed Forrest Gump fun run at Lakeside Loop in New Town Village, Owings Mills, offering a full 4.4-mile loop or a 1-mile out-and-back option. The event is free and participants are encouraged to wear the red hat, yellow top and red short..