Trail Running Calendar Delaware 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.

Join the inaugural Wild & Rooted 5K at Mt. Cuba Center for a scenic trail through meadows, forests and rolling hills. Stay after for live music, guided nature tours, hay wagon rides and drinks amid restored native landscapes.

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.

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.