Cleveland Way Challenge | 109 miles | 4 days

Back for our Third year!

Take on the Cleveland Way Challenge where you'll conquer 109 miles of stunning moorland and Coastline, passing some of the most stunning scenery the UK has to offer!

Starting in Helmsley, this in-person event is perfect for adventurers and nature lovers alike. Get ready to immerse yourself in breathtaking views and push your limits on this epic journey

You'll need resilience in bucket loads and stamina to keep going on this multi-day challenge. Camping in the great outdoors each evening (Campsites with hot showers and amenities)*
*Upgrade to shepherds huts, bunk and hostel, where available

Challenge options

4 days Full challenge - 109 miles 18-21 April (Helmsley to Filey)

2 Day inland section - 58 miles 18-19 April (Helmsley to Saltburn)

2 Day Coastal section - 51 miles 20-21 April (Saltburn to Filey)

1 Day - section of your choice

Choose Your Challenge
At Endurotrek, 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.