The Cleveland Way Challenge

The Cleveland Way Challenge

The Cleveland Way is a multi-day trekking event organized by Endurotrek that follows a 109-mile route through North Yorkshire. The full journey begins in Helmsley and concludes at Filey Beach. The course is divided into four distinct stages: Helmsley to Osmotherley, Osmotherley to Saltburn, Saltburn to Robin Hoods Bay, and finally Robin Hoods Bay to Filey.

Participants can choose from several distance and duration options:

• 109 miles (Four Day Challenge)
• 58 miles (2 Day inland section)
• 51 miles (2 Day Coastal section)
• 25 miles (1 day of challenge)

The event is designed as a non-competitive challenge rather than a race. It features three different categories based on self-sufficiency and pack weight. The Enjoy category includes baggage transfers so participants carry only daily essentials. The Endeavour category requires a minimum pack weight of 10 kg, while the Endure category requires a minimum of 15 kg for a full expedition experience.

The registration includes three nights of camping at equipped sites with hot showers, though upgrades to bunk barns or hostels are available. The organizers provide official checkpoints with drinks and snacks, medical support, and baggage transfers for specific categories. All finishers receive a challenge certificate. Transport via bus is available to Helmsley from York, Malton, or Scarborough, and a mini-bus service from the finish in Filey back to the start is available upon request. Visit the organization's website for the most recent information.