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 run and walk at Brandywine Creek State Park with marked 5 and 10 mile courses; proceeds benefit local youth cycling and park groups.
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 ultraruns at Killen's Pond State Park offering a 3.1-mile loop with 50K, 24-hour, and 100-mile options; limited, self-supported entries and basic facilities.
May 2027
A multi-distance event in Lewes, Delaware with 5K, 10K and half marathon options plus race walk and heavy march categories. The weekend includes an educational exhibit, vendors and live music while supporting wounded warriors and homeless veterans.
5K at Harvest Ridge Winery crossing MD and DE through vineyards, wooded trail and country road, with live music, a food truck and complimentary wine and keepsakes.
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.