Trail Running calendar near Dewey Beach 2025-2026

Join the Horseshoe Crab Hustle on November 9 in Ocean View, DE for a scenic 10k or 1.5 mile fun walk on Fresh Pond trails, starting at Bethany Brewing. Stay for craft beer, live music and support the Delaware Center for the Inland Bays.

Experience hardwood forests, boardwalk bridges, and fall foliage at the Talaria Trail Run in Laurel, DE on November 15, 2025. Run a 4.5 mile loop or enjoy a 2 mile walk around Trap Pond State Park while supporting Legacy Academy.

Run Of The Mill is a grassroots 5 and 10 mile trail run at Brandywine Creek State Park on November 15. No frills, scenic meadows and punchy hills; bring a suggested day of donation to support local nonprofits.

Tuckahoe 25k in Queen Anne Maryland is a scenic trail run with runnable hills and rooty, muddy sections. Three aid stations and event swag await finishers on Saturday, November 22 for a fun, rugged autumn challenge.

Kick off Thanksgiving in Vineland with the South Vineland Thanksgiving Run, a fun 3 mile cross country style course at Anthony Campanella Park. Family friendly, competitive awards, proceeds support the Friends of Vineland Public Library.

Enjoy the Williamstown Badgers Turkey Trot 5K at Autumn Lake Winery on Thanksgiving morning, a family friendly trail run over dirt, grass and sand. Run for a cause with proceeds to Honor Flight NJ and timed results with awards.

Join the festive 27th Milford Reindeer Stampede at Killens Pond State Park on November 29, 2025 for a chip timed 5K run or competitive walkers only 5K. Enjoy a long sleeve tee and a cozy post race party with treats and photos.

Angela Ivory Memorial Trail Races at Killens Pond State Park on Jan 24 and 25 offer ultra distances including 50k, 100 mile and 24 hour events. The 50k is full with no wait list; enter another distance and drop in on race day if spots open.

The Algonquin 50K is a community driven nonprofit trail race at Pocomoke River State Park starting and finishing at Milburn Landing. Expect mostly flat sandy trails, well stocked aid stations, and a friendly low key ultrarunning atmosphere.

The The Ripper - Sunrise to Sunset will take place in Pocomoke City on Saturday 2 May 2026.

Join Race4Warriors in Lewes on May 9, 2026 for 5K, 10K or half marathon courses through Cape Henlopen, Fort Miles and Rehoboth Beach. Support Wounded Warriors and homeless vets while enjoying exhibits, live music and finisher medals.

Run the Vineyards at Bohemia Manor Farm on Aug 1 features scenic 5K and challenging 8K routes through vineyards, riverside views, and wooded trails. Finish with a souvenir wine glass, live music and a waterfront after party for all to enjoy..