Chesapeake City
Trail Running Calendar near Chesapeake City 2026-2027
Explore the top trail runs near Chesapeake City for 2026-2027! We've gathered 19 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Donation-based 5- and 10-mile trail run/walk through Brandywine Creek State Park in Wilmington benefiting local cycling and park organizations.
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.
A self timed 5k from Made Me Mine in Abingdon with walking option, stroller friendly course and parking at Constant Friendship Shopping Center.
A 5 km on the Mason-Dixon Trail in Darlington with two multi-loop challenge options and self-timed results, free registration.
A self-timed 5 miles loop in Bel Air that starts and finishes at Southampton Middle School and follows part of the Bel Air Town Run Course.
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.
A club 5 km run and walk on the new section of the Ma and Pa Trail from North Avenue Trailhead in Bel Air with self-timing and on-site merchandise.
A community New Year's Eve event in Bel Air offering a self-timed 5K at Cedar Lane Park with a family countdown and a sparkling cider toast after the run.
January 2027
March 2027
HAT Run 50K is a trail ultramarathon in Susquehanna State Park with nearly 4,300 feet of climbing, two 14 mile loops and four stream crossings.
April 2027
A turtle themed 5K at Hopkins Farm Brewery in Havre De Grace raising funds and awareness for the Susquehannock Wildlife Society. The trail race includes wooden participant medals, costume prizes, and an after party with live music.
May 2027
A morning 5K held as part of the Fair Hill Scottish Games on May 15, 2027, in Elkton, MD, with on-field entries accepted, an entry fee that includes admission, and cash prizes plus trophies for top finishers.
A 20-mile single-loop hike at Fair Hill NRMA on May 22, 2027, with aid stations, a finisher medal, and roughly 1,600 ft of elevation gain.
A chip-timed 5K at Harvest Ridge Winery in Marydel DE with vineyards, a wooded trail, age group awards and a complimentary glass of wine for finishers over 21.
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.
August 2027
Trail races at Bohemia Manor Farm Winery with 5K and 8K courses through vineyards, riverfront and woods, chip timing, awards and a waterfront after party.
October 2027
Trail races at Glenroy Preserve on October 3, 2027 offering 5 mile, 25K and 50K loops on mixed, technical terrain with multiple creek crossings and four aid stations.