Trail Running calendar near Parsonsburg 2026-2027

We have found 12 Trailruns within 80 miles of Parsonsburg. See below where and when you can find the races.

A 10-mile trail run through the pine and laurel of Maryland's Pocomoke State Forest. This cupless race has a 3-hour cutoff and limited parking, so plan ahead. The course is marked with arrows and flags for navigation.

Experience a scenic trail run through the forests and fields of Rosaryville State Park. Choose from several distances on fast and smooth terrain located just off the Capital Beltway in Maryland.

Run along the paved B&A Trail in Maryland at this established event featuring a full and half marathon. Managed by the Annapolis Striders, it offers a well supported experience starting at Severna Park High School.

May 2026

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.

June 2026

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 on June 14, 2026 for a scenic run along the bay that supports the Dewey Beach Patrol. Chip timing, age group awards, and a festive post race party with food and beer make it a must for local runners.

September 2026

The Pemberton 24 is a unique 24-hour challenge in Maryland's Pemberton Park. Runners and teams attempt to complete as many hourly 5 km loops as possible, earning points for each one. It's a test of endurance with a supportive camp atmospher..

October 2026

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.

November 2026

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 returns for its 8th year on November 21, 2026. This 25-kilometer trail run features a mix of single track and horse trails with three fully stocked aid stations. The event proceeds rain or shine, offering awards and swag fo..

Join the 28th annual Milford Cross Country Booster Reindeer Stampede 5k this November in Milford, Delaware. This long running community event features a 5 km race for all participants.

February 2027

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