Wilmington
Trail Running Calendar near Wilmington 2026-2027
Explore the top trail runs near Wilmington for 2026-2027! We've gathered 48 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Family-friendly Halloween 5K and untimed 1-mile at The Bates Motel in Glen Mills with costumes, a costume contest, and proceeds benefiting the local fire company.
A Halloween 5K trail run at Old Stone Cider with costumes encouraged, live music, vendors and a food drive benefiting the Chester County Food Bank.
November 2026
Experience an off-road race weekend at Yeager’s Farm & Market featuring 4 and 10 mile trail runs. Enjoy a local atmosphere with post-race beer and bagels and earn a unique long sleeve tech shirt.
A six-hour trail challenge in Coatesville where runners complete a timed 5K each hour, aiming to finish six laps for a medal and national ranking.
A chip-timed 5K and an untimed 1.4 mile walk with live music, contests, food, games, awards, and proceeds supporting an entrepreneurship endowment at UC Berkeley.
Trail runraiser in Brandywine Creek State Park with 5 mile and 10 mile routes, free registration and a suggested donation to local cycling and park groups.
A trail and gravel running event in Wissahickon Valley Park offering 10 km, 10 mile and half marathon options with chip timing, aid stations, limited field size, and a post-race party with live music and warm food.
A fundraising run on November 8 2026 at Cynwyd Heritage Trail in Bala Cynwyd offering a 5K and 1-mile fun runs to support pups in training.
A scenic 5K at Milburn Orchards in Elkton on November 8, 2026, across orchard and farm trails with a portion of proceeds donated to local organizations.
Trail festival at Independence Park on 11/15/2026 with multiple races, multi-hour events, live music, food trucks and a community walk.
A trail 5K at Autumn Lake Winery on Thanksgiving Day with timed results, awards for top three men and women, and proceeds benefiting All Mutts Matter Rescue.
A club race in Philadelphia featuring an approximately 5.6 miles hilly course with a grassy cross country segment and club team scoring.
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.
Experience a 5k trail race through the scenic woods of Haverford Reserve with post race refreshments and long sleeve shirts for pre registered participants.
An 8.4 miles Philadelphia race along the Schuylkill River with Racejoy live tracking, chip timed splits, and awards supporting Fairmount Park maintenance.
Experience a fast and flat end of year ultra at Cooper River Park. Run a paved 3.75 mile loop featuring views of the Philadelphia skyline and access to a fully stocked aid station throughout the day.
January 2027
April 2027
A reborn six day track ultrarunning event at Cooper River Park offering timed events from six hours up to 144 hours.
A trail marathon and half marathon in Wissahickon Valley Park on April 10, 2027, featuring technical single track trails and significant climbing. The event includes race day bib pickup, live accordion music and a post race pizza party.