Wilmington
Trail Running Calendar near Wilmington 2026-2027
Explore the top trail runs near Wilmington for 2026-2027! We've gathered 51 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A vineyard-based event at William Heritage Winery featuring a chip-timed 5K, a kids 1 mile, and a 1 mile walk with awards, shirts, and finish-line refreshments.
A short yoga session followed by a chip timed 5K at Penns Woods Winery in Chadds Ford, featuring a vineyard course, race shirts, postrace music, and a wine option for 21 plus.
The Boxers' Trail 5K in Strawberry Mansion on September 19, 2026 offers run, walk, and youth options along a trail that passes forests, meadows, creeks, historic mansions and playgrounds. Proceeds support youth programs at Mander Playground.
Trail runs, a 2 mile walk and a kids race at Ramsey's Farm in Wilmington with proceeds supporting local Delaware charities.
A single day endurance walk at the Schuylkill Center with 7, 14, 21, or 28 mile loop options and optional weighted rucking inside a 10 hour finish window.
Teams of 6 to 13 run a 26 leg relay on a one mile trail loop at The Woodlands in Philadelphia, using custom batons and a torch carrying final 0.2 mile runner.
A community 5K and 1 mile kids run in West Grove PA on September 26 2026 supporting Avon Grove High School cross country with a three-loop grass course and race-day refreshments.
A dog friendly fundraising event at Bellevue State Park on September 27, 2026 featuring a scenic 5K and a one mile Mutt Mile, with race timing, awards for dogs and people, vendors, a costume contest, and merchandise.
October 2026
Experience a cross country 5K or a 1.5 mile walk through scenic woods and streams followed by live music and a bonfire to support land conservation.
Trail-based five mile race and two mile fun walk at Camp Innabah in Spring City, PA on October 3, 2026. Proceeds support summer camping programs and scholarships, with a pancake breakfast and awards for overall and age groups.
A non-profit, ninja warrior style obstacle course in Mullica Hill, NJ with an approximately 4 mile course and 12 tiered obstacles. Individual and team scoring uses tiered points and age rules require adult accompaniment for 10 to 14 year olds.
Trail races at Glenroy Preserve on October 4, 2026: 5 mile, 25K, and 50K loops with creek crossings, aid stations, and post-race food and beer.
A community trail day at McKaig Nature Center featuring a chip-timed 5K, a one-mile Monkey Rock Miler, a free kids race, a chili cook-off, event shirts for timely registrants, and awards across multiple age groups.
Cross country meet at Belmont Plateau in Philadelphia featuring men's 8,000 meter and women's 6,000 meter college/open races. Both courses are described as true cross country routes and include Flagpole, Parachute and Nursery Hills.
Test your endurance at Autumn Lake Winery with a unique hourly 5 km challenge. Choose from 6, 12, or 24 hour individual and relay events across trails and vineyards in Williamstown.
A community cross-country 5K in Haddonfield on October 17, 2026 with pre-race packet pickup, onsite registration options, entrant T-shirts, awards by overall and age groups, and accommodations for visually impaired participants.
Trail races at Parvin State Park offer a half marathon and a 6 hour lap event on a mostly trail lollipop loop. The event is cupless and uses an aid station at the start and finish.