Wilmington
Trail Running Calendar near Wilmington 2026-2027
Explore the top trail runs near Wilmington for 2026-2027! We've gathered 39 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Two day off road race weekend in Phoenixville PA with 4 mile and 10 mile runs, a Squatchy Challenge medal for both days, plus beer and bagels.
A 6 hour trail challenge in Coatesville where runners complete a 5K each hour; finishing all six laps earns a medal and combined times count toward local and world rankings.
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.
Donation-based 5- and 10-mile trail run/walk through Brandywine Creek State Park in Wilmington benefiting local cycling and park organizations.
A fundraising stair climb at Lincoln Financial Field on November 7, 2026 where participants climb 1,500 stairs to support the Cystic Fibrosis Foundation.
Public fitness event at the Rocky Steps where participants try to climb 72 steps in under 12 seconds and compete in an Orange Toss Sprint.
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 with races from 4 and 8 miles to 3 hour and 6 hour formats, plus a 2 mile walk, music, and vendors.
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 Thanksgiving morning Turkey Trot along the Schuylkill River, a 5 and 5/8 mile run from Malta Boat Club with club divisions and prizes chosen by finish order.
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.
Experience a 5k trail race through the scenic woods of Haverford Reserve with post race refreshments and long sleeve shirts for pre registered participants.
A backyard ultra in Conshohocken where runners repeat roughly 4.1 mile loops each hour until one remains, with proceeds supporting Team Foster's veterans and service dog work.
An 8.4 miles Philadelphia race along the Schuylkill River with Racejoy live tracking, chip timed splits, and awards supporting Fairmount Park maintenance.
Trail run at Blackrock Park with a chip timed 5K run in heats, a Little Tykes obstacle dash for ages 3 to 6, and proceeds benefiting Ridley United Soccer Club.
A 3.1 mile holiday fun run in Manayunk with festive attire, footwear demos, and a canned goods donation drive for North Light Community Center.
Eight hour loop race on a 3.75 mile paved course at Cooper River Park on December 13, 2026, with a single aid station and a cupless policy.