Delaware
Delaware Trail Running Calendar 2026-2027
Explore the best trail runs in Delaware for 2026-2027! Our updated list features 11 exciting trail runs across the region. Find your next trail run in Delaware below and join the trail community at these great events!
November 2026
An evening 5K and 1 mile walk on a farm in Lincoln DE featuring horses, Latin music, cultural activities, food and vendors.
Donation based trail event at Brandywine Creek State Park offering 5 and 10 mile routes, marked course open four hours, with proceeds benefiting local cycling and park organizations.
A 10K run and a 1.5 mile non-competitive walk at Bethany Brewing Company with trails in Fresh Pond State Park to benefit the Delaware Center for the Inland Bays.
A community 5k run/walk and a separate competitive walking 5k at Killens Pond State Park on November 28, 2026. The event supports Milford High School Cross Country and features chip timing, awards, shirts, and post race refreshments.
Open 5K cross country championship at Brandywine Creek State Park on November 28, 2026, with registration fees and proceeds supporting a local high school shoe program.
December 2026
A 5K cross-country run at Sharp Farm in Middletown on Dec 5, 2026, across fields, forest edges and wide trails with proceeds supporting Delaware Wild Lands.
January 2027
Trail event at Killen's Pond State Park near Felton DE offering 50K, 24 hour and 100 mile options on a mostly dirt 3.1 mile loop.
May 2027
Multi distance races at Cape Henlopen State Park honoring Middle East veterans with competition, an educational exhibit, and a celebration with vendors and live music.
A chip-timed 5K at Harvest Ridge Winery in Marydel DE with vineyards, a wooded trail, age group awards and a complimentary glass of wine for finishers over 21.
June 2027
Five consecutive race days June 2–6, 2027 across DE MD PA NJ and NY offering marathon, half, 50K, 10K and 5K with daily aid stations and collectible medals.
October 2027
Trail running at Lums Pond State Park on 10/03/2027, offering a half marathon and a 10K over mostly flat single track and wide trails.