Trail Running calendar near Parsonsburg 2026-2027

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.

Say My Name 5k and 1 mile Walk in Lewes raises funds for Rylie’s Smile Foundation while participants run or walk the Cape Henlopen State Park Trail. The event includes a virtual 5K option, commemorative signage, post-event awards, and race..

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..

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 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 six hour endurance run and a three person relay at Quiet Waters Park in Annapolis. Loops are about 4.25 miles with two aid stations on course, awards by category, and a branded sport duffel premium.

Looped trail ultras at Killen's Pond State Park near Felton, DE with 50 mile, 50 kilometer and 12 hour options on a roughly 3.1 mile mostly dirt loop. The format is self supported with water provided and manual lap timing.

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.

Muddy Dash Mechanicsville is a 5K mud run at Budds Creek Motocross Park with obstacles, mud pits and slides plus a festival style after party with music, food and beer. Registration options include standard and VIP packages.

A 24 hour event at Pemberton Park in Salisbury, MD where individuals and four person teams run repeated 5K loops. Scoring is point based with bonuses for night runs, placing points, and awards for top individuals and teams.

Community trail event at Camp Barnes in Frankford, Delaware offering 6.2 and 3.1 mile runs, 1 to 3 mile family walks, and a Kiddie Color Run. Post race lunch and live bluegrass music support Mariners Bethel youth ministries.

An endurance running event in Woodbine NJ offering 6-, 12- and 24-hour individual races plus 12- and 24-hour relays. The course uses 5.5-mile dirt laps with few roots and the venue provides camping, cabins, showers and a sauna.

A fall trail event at Trap Pond State Park featuring a 4.5 mile loop on the Bob Trail and a 2 mile walk. Participant fees support Legacy Academy.

Trail races of **50K** and **20K** loop Rosaryville State Park single track in Upper Marlboro, MD, with two aid stations, a drop bag area, participant limit, and post race food and festivities.

A trail 25k in Queen Anne, Maryland on November 21, 2026. Mostly single track with runnable hills, three aid stations, food options, and awards for the top three men and women.

A cross country style 3 miles race at Anthony Campanella Park in Vineland, NJ, welcoming runners and walkers of varying ages. Awards for top overall finishers and multiple age groups; online registration with several payment options.

A late November 2026 community 5k at Killens Pond State Park offering a 5k run walk and a competitive walking 5k with chip timing, age group awards, long sleeve shirts, and a post race refreshment selection.

A trail 5K on February 20, 2027 at the Wicomico Ranger Station in Parsonsburg, MD that raises funds for 4STEPS therapeutic riding programs, with age/gender prizes in Amazon gift cards and a $32 registration fee.