Pepper Pike
Trail Running Calendar near Pepper Pike 2026-2027
Explore the top trail runs near Pepper Pike for 2026-2027! We've gathered 28 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
Looped hill endurance event on a 1.1 mile course with 140 ft gain per lap, offering multiple timed challenges and fundraising to support cancer patients.
A fundraising event at the Wolstein Center in Cleveland on August 29, 2026 featuring patient recognition, research updates, a silent auction and multiple participation categories.
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 events at Camp Manatoc in Peninsula, Ohio featuring a half marathon, 15k and 5k on mostly single-track technical trails with dogs allowed.
A Conquer the Castle preview run at AB Williams Memorial Woods on an unmarked 10+ mile loop with no aid stations and bathrooms at about 3.75 and 5 miles, registration required.
Trail race at Richfield Heritage Preserve with 50K, half marathon and 10K on a six mile loop through single track, fields and camp roads; organized by Fast Girls Running Company.
A community run/walk on September 19, 2026 at Stone Mad Pub in Cleveland featuring a chip timed 5K and a 1 mile walk, with age group awards, event T shirts, food, and a post race beer for those 21 and over.
A 5K and an 800 m kids run through the Orange City Schools campus on September 27, 2026, with proceeds benefiting the OHS Cross Country team.
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.
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.
A certificated 100 mile trail endurance run in Akron, Ohio with front and back 50 mile options along the Ohio & Erie Canalway Towpath.
A hill-climbing challenge at Brandywine Ski Resort on October 10, 2026 where runners repeat a 1 mile loop with 375 ft gain and finish on a steep 0.12 mile 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.
A community fundraiser in Cleveland Heights featuring a rugged trail run with water crossings and a neighborhood one mile walk to benefit EDWINS Leadership & Restaurant Institute.
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.
Outlast Cleveland is a 6 hour trail endurance challenge in Garrettsville, OH where runners complete a 5K every hour for six rounds. Finish all six to earn the OUTLAST medal and a place on the national leaderboard.
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.