Trail Running calendar near Lewes 2025-2026

Join the EKR Leftover Run on November 1 at Elk Township Recreational Park for a friendly timed 5k along the scenic Elephant Swamp Trail. Enjoy unique leftover swag and competitive age group awards in a fun, low key community race.

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.

Talaria Trail Run is a fall trail event held at Trap Pond State Park in Laurel, Delaware. It features a 4.5-mile Race and a 2-mile Walk. The course follows the Bob Trail—a 4.5-mile loop around the 90-acre Trap Pond—winding through hardwood..

Run Of The Mill 5/10-miler walk/run trail runraiser takes place at Brandywine Creek State Park in Wilmington, Delaware (Hawk Watch Parking Lot, 41 Adams Dam Road, 19807). Participants choose a 5-mile or 10-mile marked course through Delawar..

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.

Challenge yourself at Frosty Looper, an 8 hour timed race around scenic Cooper River Park on December 14, 2025. Mostly flat paved loops with a few hills, aid at the start and finish, and every finisher receives a custom race item.

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.

Run or stroll Matzah Miles on a scenic family friendly trail in Medford with a timed 5 km, one mile family walk and Kids 50 Yard Dash. Enjoy music and matzah treats while supporting inclusion through Open Hearts Open Doors.

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 offers 5K and 8K courses through vineyard, river and wooded trails, with chip timing and scenic views. Finish with a souvenir wine glass and waterfront after party with live music and food trucks.