Willoughby Hills
Trail Running Calendar near Willoughby Hills 2026-2027
Explore the top trail runs near Willoughby Hills for 2026-2027! We've gathered 20 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A 5K cross country race at Penitentiary Glen Reservation in Willoughby on August 18, 2026. The course mixes grass fields and crushed limestone trails, with separate races for male and female competitors and open entry for kids and adults.
Endurance race on one of Cleveland's steepest hills where runners complete as many laps as possible within 1, 3, 6, or 12 hour limits. All registrations and donations go directly to cancer patients through the Nelson Family Foundation.
September 2026
An evening trail event at Hemlock Nature Preserve on September 4, 2026 offering a 7-mile (about 11 km) run, ruck, or hike plus a 1-mile option, a twice crossed stream, live German music, biergarten, chip timing, awards, and post-race food.
Trail races at Richfield Heritage Preserve offering 50K, half marathon, and 10K on mixed single track, bridle trails, fields, and camp roads in mid September.
A five-event trail series in Cuyahoga Valley National Park with weekly themed Tuesday evening races from late September through October. Distances are 3 to 5 miles and the final event at Camp Butler is dog friendly.
October 2026
A community event at Forest Ridge Preserve featuring a chip timed 5K and a 1.5 mile self guided hike through the Chagrin River valley. Proceeds support the Moreland Hills Parks Commission and registrants by September 20 receive a commemorative shirt.
A charity event in Cleveland Heights featuring a 3.5 mile off-road trail with water crossings and a 1 mile neighborhood walk. Proceeds benefit EDWINS Leadership & Restaurant Institute and awards are given by age group.
Experience the peak of autumn foliage at the Chippewa Creek Challenge in the Brecksville Reservation. Run a half marathon trail course through the heart of the Cleveland Metroparks amidst vibrant fall colors.
Trail race at Ledge Lake Lodge in Hinckley Ohio offering 13, 26 and 52 mile options on one, two or four loops through the Cleveland Metroparks Hinkley Reservation. The course includes rocks, roots, fields and about 1,600 feet elevation per loop.
November 2026
Test your endurance at the North Chagrin Reservation with races ranging from a 5k to a 100k ultramarathon. Discover scenic forest trails featuring creek crossings and a unique knighting ceremony for long distance finishers.
Timed individual and relay races at South Mastick in Rocky River Reservation on November 7, 2026, featuring 3 hour and 6 hour timed events plus 4 mile races on a 2 mile loop, chip timing, and awards across multiple divisions.
A two-loop trail run of about 15k through North Chagrin Reservation, passing Squires Castle, Buttermilk Falls, and Oxbow Lagoon. It is the final race of the Dirty Trail Series and includes a year-end party with awards and prizes.
February 2027
March 2027
April 2027
A memorial 5K trail run through the wooded trails of Camp Manatoc in Peninsula, Ohio on April 18, 2027. Registration is open March 1 through December 31, 2026 with a $30 fee. Proceeds support camp financial assistance and participants receive a custo..
May 2027
Multiple timed ultramarathon options on a 2.92 mile gravel and trail loop near Richfield, Ohio. Part of the proceeds supports capital improvements at the Richfield Heritage Preserve.
October 2027
Multiple-distance Spartan obstacle weekend at Southington Off Road Park with Sprint, Super and Beast courses across rugged off-road trails.