Willoughby
Trail Running Calendar near Willoughby 2026-2027
Explore the top trail runs near Willoughby 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.
September 2026
A five-event trail series in Cuyahoga Valley National Park from late September through October, featuring short courses, participant swag, and a secret twist at each event.
October 2026
Run or hike through Forest Ridge Preserve on October 3 to support Moreland Hills parks; proceeds fund trail and park improvements.
Two hour night event at Geauga Park District where participants run, jog, or walk as many 0.85 mile laps as possible to earn a Space Race medal and planet ribbon.
Five weekly trail races in Cuyahoga Valley National Park from Sept 29 to Oct 27, 2026, each 3 to 5 miles at a different location with series swag and a surprise twist.
A timed hill-climb event at Brandywine Ski Resort on October 10, 2026 where runners tackle repeated 1 mile loops with steep elevation and a short final climb.
A course preview for Conquer the Castle at AB Williams Memorial Woods in Mayfield on October 10, 2026, featuring an unmarked loop of about 10 miles with no aid stations.
Five weekly trail races in Cuyahoga Valley National Park from Sept 29 to Oct 27, 2026, each 3 to 5 miles at a different location with series swag and a surprise twist.
A charity trail run and neighborhood 1-mile fun walk at EDWINS in Cleveland Heights benefiting EDWINS Leadership & Restaurant Institute, with awards by age group.
Five weekly trail races in Cuyahoga Valley National Park from Sept 29 to Oct 27, 2026, each 3 to 5 miles at a different location with series swag and a surprise twist.
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 trail event at Ledge Lake Lodge with 13, 26, or 52 mile loop options through Hinckley Reservation, rocky and rooty terrain and a 16 hour cutoff for the double.
Five weekly trail races in Cuyahoga Valley National Park from Sept 29 to Oct 27, 2026, each 3 to 5 miles at a different location with series swag and a surprise twist.
November 2026
Fall trail race at North Chagrin Reservation on Nov 7, 2026 with looped distances from 5K to 100K, ruck divisions, chip timing, and an optional hill climb at Squire's Castle.
Timed runs and relays on a 2 mile loop at South Mastick in Rocky River Reservation, including 6 hour and 3 hour time events plus 4 mile races.
A two-loop trail running event at North Chagrin Reservation in Willoughby Hills, Ohio, the Dirty Dirty 15K is the final race of the Dirty Trail Series, passing Squires Castle, Buttermilk Falls and Oxbow Lagoon and ending with a series party.
February 2027
Trail races on 02/20/2027 at North Chagrin Reservation with 15K and 8K options plus a heated shelter and hot chocolate bar.
March 2027
Trail races at Brecksville Reservation from Meadows Picnic Area, offering a 10K (hikers welcome) and a half marathon.
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
A 24 hour trail endurance event on a 1 mile loop through woodland and rock formations near Kirtland, Ohio, with a 100 mile race option and timed entries.