Trail Running calendar near Fruitland 2025-2026

Run the 16th annual Rosaryville Veterans Day Trail Race at Rosaryville State Park with 50K and 20K routes through woods and meadows on rolling single track trails. Limited to 250 runners with aid stations and awards.

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.

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.

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.

Explore a scenic loop around Saint Marys Lake and Salem Forest with 17K, 34K and 50K options on mostly single track trails and about 500 ft of climb per lap. Limited to 100 runners, with pancakes served at the finish.

Challenge yourself on the scenic B&A Trail in Severna Park with marathon or half marathon options on March 29, 2026. Enjoy USATF certified courses, friendly aid stations and a commemorative finisher medal.

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.