Trail Running calendar near Salisbury 2026-2027

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 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 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 timed six-hour endurance event at Quiet Waters Park in Annapolis with solo and three-person relay formats. The course is about 4.25 miles per loop, with aid stations on the route and awards by overall and age-group distance.

An 8K cross-country race at Anne Arundel Community College on August 2, 2026, part of the Annapolis Striders Championship and Maryland/DC RRCA Grand Prix Series, with pre-registration fees and race day registration available.

Looped ultramarathons at Killen's Pond State Park near Felton, DE, with 50 mile, 50K, and 12-hour options on a shaded 3.1 mile dirt loop. The event is self-supported, manually timed, and limited to 30 entrants per race.

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.

The Muddy Dash - Maryland will take place in Wicomico Shores on Saturday 29 August 2026.

A 24-hour event at Pemberton Park where individuals and four-person teams run repeated 5K loops, earning points per finish and for placing, with bonus points for late-night miles and a big bonus for completing all 24.

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 at Rosaryville State Park near Upper Marlboro, MD. Courses run on a 9.5 mile perimeter trail through woods and meadows with aid stations, drop bags, and a strict no-headphones policy.

A 25K trail race in Queen Anne Maryland on November 21 2026 featuring mostly single track, runnable hills, three stocked aid stations, awards for top finishers, and no rain date.

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.

A multi-distance event in Lewes, Delaware with 5K, 10K and half marathon options plus race walk and heavy march categories. The weekend includes an educational exhibit, vendors and live music while supporting wounded warriors and homeless v..