Trail Running calendar near Lewes 2025-2026

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 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.

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.

Frosty Looper is an 8 hour timed run at Cooper River Park near Philly around a fast 3.75 mile loop with skyline views. Run as many laps as you can, enjoy aid station food and vegan options, bring a reusable cup, and take custom race swag.

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.

Tackle the HAT Run 50K in Havre de Grace, Maryland, a scenic trail challenge with rolling single track, open fields and nearly 4,400 feet of climbing. Expect stream crossings and a rewarding day on rugged, looped trails.

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.

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.

Hit the scenic B&A Trail in Severna Park for a marathon or half marathon on March 29, 2026. Enjoy wooded waterfront trails and a lively finish at Severna Park High School hosted by the Annapolis Striders.

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..