Trail Running calendar near Dewey Beach 2026-2027

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.

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..

Join the Winter Thaw Out Series: four relaxed 5k trail runs on Elephant Swamp Trail near Monroeville NJ. Enjoy a series medal, age group awards, hot chocolate after each race, and a discount when you sign up for all four.

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.

On May 9, 2026 Race4Warriors in Lewes, DE features USATF certified 5K, 10K and half marathon courses through Cape Henlopen State Park. Events include run, race-walk and a heavy march with a 15 lb pack plus an exhibit 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.

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.

Run the Vineyards at Bohemia Manor Farm offers scenic 5K and 8K courses through vineyards, waterfront and wooded trails, chip timed with live results. Finish with refreshments, a souvenir wine glass and an after party on the river.

Celebrate Labor Day at William Heritage Winery with a chip timed 5K on scenic vineyard paths plus one mile and kids races for all ages. Finishers 21 and over get a souvenir glass and a complimentary wine while supporting HEADstrong.

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.

Run the Vineyards at White Horse Winery features 10K, 5K and 1 mile on a flat scenic vineyard course supporting the HEADstrong Foundation. Enjoy a tech tee, souvenir wine glass, live music, wood fired pizza and a glass of wine.

Scenic lake loop trail runs at Lums Pond State Park offer everything from a single lap 12 KM to a 24 KM and 12 hour solo or 4 person relay. Aid stations and race day bib pickup make it a relaxed fall challenge.

Run the mostly flat, fast lollipop loop at Parvin State Park in the Hot Mess Trail Races, offering a Half Marathon or a 6 hour lap event. This cupless race asks runners to carry their own cup and pack out trash.

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.

Run a festive 5K trail through Autumn Lake Winery on Thanksgiving Day in Williamstown, NJ, with trails, grassy and sandy stretches and no time limit. Family and dog friendly, with proceeds benefiting Lucky Paws Animal Assistance.

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.

A winter trail event at Fair Hill offering 25K and 50K (two-loop) courses, stocked aid stations, and a heated activity hall at Edward L. Walls Activity Hall, with a maximum field of 600 runners.