Delaware
Delaware Trail Running Calendar 2026-2027
Explore the best trail runs in Delaware for 2026-2027! Our updated list features 16 exciting trail runs across the region. Find your next trail run in Delaware below and join the trail community at these great events!
October 2026
A farm-based 5K run and walk at Hopkins Farm in Lewes on October 10, 2026, with chip timing, awards, participant shirts, and fundraising for ag education.
Trail running festival at Lums Pond State Park on October 17, 2026 with 12 km and 24 km races, a 12-hour solo challenge, and a 4-person relay on fast lakeside single-track.
Trail races at Mt. Cuba Center on October 17, 2026 offering 5K and 10K courses through meadows, forests and ponds with garden access and post race activities.
A community 5K on Gravel Hill Road in Georgetown, DE supporting the Delaware Aerospace Education Foundation with chip timing, shirts, refreshments, and age-group awards.
Trail runs, family walks and a kids color run at Camp Barnes with races, awards, live bluegrass and a community post-race meal supporting Mariners Bethel youth ministries.
November 2026
An evening farm event in Lincoln, DE featuring a 5K run and 1 Mile walk with horses, Latin music, awards, and post-event food and vendors.
Donation-based trail event at Brandywine Creek State Park offering 5- and 10-mile distances, with proceeds supporting three Delaware cycling and park nonprofits.
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
Ultrarunning on a roughly 3.1 mile dirt loop at Killen's Pond State Park offering 50k, 24 hour and 100 mile options with basic pavilion 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.