Chesapeake City
Trail Running Calendar near Chesapeake City 2026-2027
Explore the top trail runs near Chesapeake City for 2026-2027! We've gathered 25 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A 5K walk and run on October 18, 2026 at the Ma and Pa Trail Williams St trailhead in Bel Air, MD; registration $20 from Sept 26 to Oct 15 and finishers receive a Husky medal.
A marked 5K trail race on October 25, 2026 in Kirkwood, Pennsylvania across grass fields, horse trails and dirt roads with timed divisions, ribbons, and a t-shirt option.
A Harford County Running Club Sunday run in Havre de Grace with a self timed, stroller friendly 4 mile road course and optional extra mileage around a hay field.
A Halloween 5K and family festival at Old Stone Cider with a food drive, live music, vendors, costume contests, and fundraising for the Chester County Food Bank.
November 2026
Enjoy a 5k run or walk from the lighthouse at Concord Point Park as part of the Harford County Running Club Sunday Run Series.
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 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
A spring trail 50K at Susquehanna State Park with two identical loops, about 4,300 feet of climbing and several stream crossings, supported by aid stations and volunteers.
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.