Trail Running calendar near Salisbury 2026-2027

Take on scenic trails at Killens Pond State Park in Felton Delaware with the Angela Ivory Memorial Trail Runs, offering 100 mile, 50k and 24 hour race options. A communal, challenging winter weekend where some distances fill quickly.

Delmarva Ultra Challenge 100K in Pocomoke MD pairs an overnight 50K with a morning 50K on the Algonquin course. Combine times across both runs for a rewarding and mysterious two day trail test.

Run a scenic 50K at Milburn Landing in Pocomoke River State Park, Maryland, mostly on trail with sandy sections and winter weather possible. Community supported aid stations, an 8 hour cutoff, and handmade mugs for finishers.

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..

Discover scenic trails around Saint Marys Lake near Leonardtown, MD with 17K, 34K or 50K on one to three laps through Salem Forest. Limited to 100 runners, this intimate event has rugged single track, lake views and on course aid.

Run a 10 mile trail through the Hudson Tarr tract of Pocomoke State Forest in Pocomoke Maryland on March 15, 2026. Expect creek crossings, a single aid station, limited parking, and a rugged backcountry vibe for adventurous trail runners.

Run through the woods and open fields of Rosaryville State Park with half marathon, 10K and 5K trail options plus virtual entries for March 28, 2026. Enjoy twisty but smooth, mostly flat trails hosted by EX2 Adventures.

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.

Race4Warriors on May 9 2026 in Lewes DE offers 5K, 10K and half marathon with Run, Race Walk or a Heavy March through Cape Henlopen State Park and Fort Miles. Finishers get a medallion and a lively post race party with bands and vendors.

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.

Annapolis Striders unites runners in Annapolis, MD with road and trail races from 1 mile to ultramarathon and training programs for beginners to marathoners. Enjoy community races and a lively event calendar year round.

Push your limits at the Pemberton 24, a 24 hour running challenge at Pemberton Park in Salisbury MD on September 18 to 19, 2026. Run hourly 5K loops solo or with a four person team, rest at your camp, and chase points and nightly bonuses.

Annapolis Striders unites runners in Annapolis, MD with road and trail races from 1 mile to ultramarathon and training programs for beginners to marathoners. Enjoy community races and a lively event calendar year round.

Run a rugged 25k through scenic single track and horse trails in Queen Anne, Maryland on November 21, 2026. Expect runnable hills, muddy rooty sections, three stocked aid stations, and a lively race vibe with swag and awards.

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.