Trail Running calendar near Parsonsburg 2026-2027

Experience USATF certified courses through Cape Henlopen State Park and historic Fort Miles. Choose between running, walking, or a heavy march to support veterans in this scenic Delaware event.

Test your resilience in this 24 hour endurance challenge in Annapolis. Set your own mileage goals to honor military heroes while enjoying provided meals and a community trail running environment.

Trail Trotters 5K & Fun Run at Promise Landing Farm in Upper Marlboro offers a farm-trail 5K and a fun run to support the farm's riders and programs. The event includes free parking, a shirt deadline of May 16, no pets, and refunds up to se..

Combine a 5k run or walk with vineyard scenery at Corteau Vineyards. Registration includes a wine glass, medal, and a wine pour, with age group awards for top finishers. Leashed dogs are welcome on this cross-country style course.

Join the 24th Dewey Beach Patrol 5k in Delaware for a series road race ending with a post-race party on the bay. This chip-timed event offers categories for both runners and competitive walkers.

An informal, self-supported ultramarathon at Killen's Pond State Park with 50-mile, 50K, and 12-hour options on a shaded 3.1-mile dirt loop, manual lap counting, water provided, and strict storm safety rules.

Test your endurance at the Wildwood Navy Seal Challenge with ocean swimming and beach running. Navigate sand and water obstacles in individual or team categories on the New Jersey shore.

A 24-hour event in Salisbury where individuals and four-person teams run hourly 5K loops on Pemberton Park trails. Points-based scoring, an aid station at start/finish, and awards for top individuals and teams.

Experience a scenic trail run through the Assawoman Wildlife Refuge at the 23rd annual Mariners Bethel event featuring various distances and a post race bluegrass celebration.

The Talaria Trail Run is a fall event at Trap Pond State Park in Delaware. It features a 4.5-mile race on the scenic Bob Trail and a 2-mile walk. Participation supports Legacy Academy.

The Tuckahoe 25k in Queen Anne, MD on November 21, 2026 is a 25 kilometer trail race featuring mostly single track, runnable hills, and some muddy sections. Three stocked aid stations support runners and awards go to the top three men and w..

Join the 28th annual Reindeer Stampede 5k at Killens Pond State Park for a run or competitive walk. This established event supports local cross country and features festive awards and a post race party with seasonal treats.

Support therapeutic riding programs while running through the beautiful forested trails of the Wicomico Demonstration Forest in this inaugural 5k trail race.