Trail Running calendar near Parsonsburg 2026-2027

A 100K trail event in Pocomoke, MD combining two consecutive 50K runs with combined times deciding overall winners. The first 50K is held at an undisclosed location revealed shortly before the run.

The Algonquin 50K is a community run trail ultramarathon at Pocomoke River State Park covering roughly 50 kilometers on mostly flat single track and horse paths. Aid stations appear every 5 to 6 miles and an 8 hour cutoff is enforced.

Looped trail races at Killen's Pond State Park offering 50K, 24 hour and 100 mile options on an about 3.1 mile dirt loop with low technical difficulty and limited support.

Celebrate Valentine’s Day with a fun and friendly 5K at Kinder Farm Park in Millersville on Feb 14, 2026. Enjoy a mostly flat loop with gentle hills, chip timing, and awards for top finishers in a welcoming community race.

Hit the forest trails in Parsonsburg for the 4STEPS Therapeutic Riding 5K on Saturday, February 21, 2026. Enjoy a scenic first time 5K through Wicomico Demonstration Forest while supporting therapeutic riding programs for riders with specia..

Trail races near Leonardtown, MD on an ~10.5 mile loop around a 250 acre lake, offered as 17K, 34K, or 50K with two aid stations and a 100 runner limit.

A 10 mile trail race in Pocomoke State Forest on March 15, 2026. The event is cupless with one aid station, limited parking, and packet pickup available the day before.

Trail races at Rosaryville State Park in Upper Marlboro MD on March 28, 2026 include half marathon, 10K and 5K plus virtual options. Courses run through hardwood forests, fields and equestrian trails with multiple aid stations.

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.

USATF-certified 5K, 10K and half marathon events in Lewes, Delaware with Run, race-walk, or Heavy March (15 lb pack) options, a historical exhibit, and a post-race vendor and music area supporting Wounded Warriors and homeless veterans.

A chip-timed 5k at Corteau Vineyards on June 13, 2026, featuring a two-lap cross-country style course through the vineyards, age-group awards, race swag and a wine pour. Virtual participation and packet shipping are available.

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.

Endless Summer 6 hour Run is a timed six hour event at Greenbury Point Nature Center in Annapolis on July 18, 2026. It is listed on the Annapolis Striders race calendar.

A 24-hour event at Pemberton Park where a new 5K starts every hour. Solo and four-person team divisions race for points rather than chip times, with placing points, night bonuses, and awards for top finishers.

Rosaryville Veteran’s Day on November 14, 2026 holds two races at Rosaryville State Park in Upper Marlboro, Maryland, with a 50K and a 20K. Event details and registration are listed via UltraSignup.

The Talaria Trail Run will take place in Laurel on Saturday 14 November 2026. You can run 5 miles.

The 8th annual Tuckahoe 25k is a trail race in Queen Anne, Maryland covering approximately 25k (15.5 miles) on mostly single track and horse trails. Three aid stations support runners and awards go to the top three men and top three women.

Celebrate the season at Milford Reindeer Stampede 5k at Killens Pond State Park on November 28 with a scenic run or competitive walk. Enjoy a long sleeve race shirt, post race treats and chip timing in this family friendly holiday event.