The Cleveland Way | 109 miles | 4 Day Challenge | Easter Weekend

Challenge yourself to this endurance trek along the stunning Cleveland Way, covering 109 miles over 4 days.

Day 1: Helmsley to Osmotherley

Day 2: Osmotherley to Saltburn

Day 3: Saltburn to Robin Hoods Bay

Day 4: Robin Hoods Bay to Filey

Over the course of 4 days, you'll push your limits, soak in breathtaking views, and create lifelong memories. Whether you're a season trekker or relative novice, this event is suitable for all fitness levels.

Choose Your Challenge

On an Endurotrek challenge everyone takes on the same route — but how you take it on is up to you.
Select your level of challenge and make the journey your own.
Whichever category you choose, you’ll have the full support of the Endurotrek team every step of the way.

ENJOY – Adventure at your own pace

For those who want to soak up the views, enjoy the camaraderie, and experience the trek without the full weight of the kit.
Your main baggage is transferred by our team, leaving you to carry just your day essentials — food, water, and clothing.

Perfect for first-time trekkers or those who want to focus on the journey, not the load.
Fully supported by the Endurotrek crew throughout.

ENDEAVOUR – Test your limits

For those ready to take on a moderate challenge and embrace a degree of self-sufficiency.
Participants carry a minimum of 10kg, plus food and water, managing more of their own kit while still benefiting from some logistical support.

Ideal for adventurous spirits looking to push themselves — with Endurotrek’s full support team by your side from start to finish.

ENDURE – The ultimate test

For those who crave the full expedition experience — physical, mental, and emotional.
Participants carry a minimum of 15kg, plus food and water, taking on the trek in full self-sufficient style.

This is endurance trekking at its purest — every step earned, every mile carried, with Endurotrek support always close when needed.