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  • Hickory Fox Trail, Mayfield, Ohio, 44143, United States
    OpenStreetMap Google Maps
    Distance: 3.8 km from Willoughby Hills
    Sat, Jul 11, 2026 at 9:30 AM

    Miles for Migraine will host its 9th annual 2-mile Walk, 5K Run and Relax Ohio event on Saturday July 11th at North Chagrin Reservation in Willoughby Hills. This event is a fundraiser for Migraine & Headache Awareness, Treatment & Research. It's more than a walk/run - come connect with your local migraine & headache community, listen to our speakers & visit sponsors in the festival area.

    The 5K run is professionally timed. The Walk and the Relax events are free, but donations are encouraged. All walk and run finishers receive a finisher medal.

    Dress up in your best purple flair for a chance at a fun prize!

    Funds raised will benefit Miles for Migraine free programs & services as well as the Cleveland Clinic and UH Cleveland Headache Centers to support local migraine research and fellowship training programs.

    See full details
    2 Miles5kRunVirtualWalk via RaceRoster
  • 34041 Stevens Blvd, Eastlake, Ohio, 44095, United States
    OpenStreetMap Google Maps
    Distance: 8.1 km from Willoughby Hills
    Sun, Aug 02, 2026 at 9:00 AM

    Date: August 2, 2026

    Time: 9:00AM

    Location: Eastlake North High School - 34041 Stevens Blvd, Eastlake Ohio 44095

    The Woody Williams Foundation is a charitable 501c(3) organization that pursues specific endeavors and goals through the vision of Medal of Honor Recipient Hershel "Woody" Williams. The Foundation encourages, with the assistance of the American public and community leaders, establishing permanent Gold Star Families Memorial Monuments in communities throughout the United States, conducting Gold Star Families Outreach across the country, and providing Living Legacy scholarships.

    See full details
    1 Miles5kRun via RunSignup
  • Distance: 8.6 km from Willoughby Hills
    Sun, Sep 13, 2026 at 10:15 AM

    Over the past 13 years, the Downtown Willoughby 5k has donated $238,000 to Make-A-Wish Ohio, Kentucky and Indiana. Let's keep it rolling toward $250k next September while you run or walk in beautiful DTW 5k and celebrate with your friends and community after the race.

    5kRunWalk via RunSignup
  • Distance: 6 km from Willoughby Hills
    Sun, Oct 04, 2026 at 10:00 AM

    Come out and feel the excitement surrounding our Ursuline Arrows campus!

    From our cross country and track & field team to you, we welcome you to run through Pepper Pike, the Ursuline College campus and Merici Crossings.

    Arrows Nation will be rooting for you through gradual inclines and road racing as you run to support our XC/T&F program. Immediately following the race, join in on our Ursuline Fall Festival in the main quad for food trucks, music and fun.

    All proceeds go towards the student-athlete experience both in and out of the classroom and races. We greatly appreciate your generosity!

    The UC 5K is an official 2026 Cleveland Road Race Series event. Learn More at RoadRaceSeries.com

    Race Information

    Date: Sunday, October 4, 2026

    Location: Ursuline College - Stano Athletic Center (2550 Lander Rd Pepper Pike, OH 44124)

    Race Morning Packet Pickup: 8:30 am - 9:45 am

    5K and 1-Mile Start: 10:00 am

    Post Race Celebration: 11:00 am

    Fees (5K and 1-Mile)

    • $35 - through race morning

    • Students, faculty, alumni and friends receive $5 off with the Ursuline College discount code.

    • If paying by cash or check, a paper form must be printed and mailed to Hermes Sports at the bottom of the page the Wednesday before race day.

    What's Included

    • A Chip Timed 5K and Race Bib

    • A UC Race Shirt *shirt sizes guaranteed if registered by 9/15

    • A Raffle Ticket

    • Post Race Refreshments

    • Awards for the Top Male Female and Team Finishers

    Make a Team

    • Find at least 2 friends and create your own team for the UC 5K!

    • This 3+ person Team will race for the Top Team Award by taking the lowest 3 combined finisher times in the 5K.

    • During online registration, the team captain will CREATE a team name and team members will JOIN that team when they register.

    • Learn More: HERE

    See full details
    1 Miles3.1 Miles5kRunWalk via RunSignup
  • Distance: 5.3 km from Willoughby Hills
    Sat, Nov 07, 2026 at 5:00 AM

    Knights, ruckers, and trail champions — prepare to take to the trails once again for the 2026 Conquer the Castle Trail Race at North Chagrin Reservation in Cleveland, Ohio!

    Join us on Saturday, November 7, 2026, for a day of epic trail racing through the stunning fall colors of the Cleveland Metroparks. Whether you’re running, hiking, or rucking, there’s a challenge for every adventurer.

    Choose from multiple distances, from the 5K, 10 Mile, and 20 Mile, to the endurance-testing 50K and 100K ultramarathons, plus ruck options for those ready to test their strength and stamina.

    Experience one of Ohio’s premier fall trail races, where every climb, creek crossing, and castle challenge brings you closer to conquering the course — and earning your place among the legends. ⚔️🍂

    Registration Includes

    • Custom unisex race shirt included for all participants or upgrade to a hoodie!

    • Custom Finisher Medal

    • Race Bib

    • Chip Timed Run

    • Stocked aid stations

    • Post-race snacks

    • Awards: Top 3 Female & Male finishers for 100K, 50K, 20 Mile (morning & afternoon), 20 Mile Ruck, 10 Mile, 10 Mile Ruck, & 5K

    100K Finishers will receive a belt buckle

    • Be Knighted (this is for the 100K, 50K, 20 Mile (morning & afternoon), 20 Mile Ruck, 10 Mile, & 10 Mile Ruck)

    Schedule

    Friday, November 6th

    • 4-6:30 PM | Early Packet pick-up | 2nd Sole, 18636 Detroit Avenue, Lakewood, Ohio 44107

    Saturday, November 7th | Forest Picnic Area, North Chagrin Reservation

    • 4:00 AM | Early send off for 100k and 50k runners*

    • 4:00 AM | Packet pick up (Will be open throughout the day)

    • 5:00 AM | 100k starts

    • 6:00 AM | 50k starts

    • 7:00 AM | 20 Mile & 20 Mile Ruck starts

    • 8:00 AM | 10 Mile & 10 Mile Ruck starts

    • 9:00 AM | 5k starts

    • 1:00 PM | 20 Mile afternoon start

    • 3:00 PM | 10 Mile afternoon start

    • 6:00 PM | must start last loop for 100k

    • 9:00 PM | race closes/timing crew packs up.

    *Starting in the 4:00 AM Early Send Off voids you from Age Group and Overall Awards, but not the race or listing in results.

    **Awards for Age Groups and Overall will be handed out throughout the day.

    Participants who start a loop (loops) after 3:00 PM must have a headlamp or another source of light to help guide them on the trail.

    Important race locations

    • Start/Finish | Forest Picnic Area

    • Event parking | AB Williams Memorial Woods & North Chagrin Nature Center

    • 5 Mile Aid Station | Squire's Castle Shelter

    Review the Refund Policy & and Bib Transfer policies

    See full details
    3.1 Miles10.3 Miles20.6 Miles20.69 Miles50k100kRunTrailUltra via RunSignup
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