Cleveland Way Challenge 2026

Name: Cleveland Way Challenge 2026
Start: 2026-04-03T07:30:00+01:00
End: 2026-04-06T18:30:00+01:00
Location: Cleveland Way National Trail

Schedule

Fri, 03 Apr, 2026 at 07:30 am to Mon, 06 Apr, 2026 at 06:30 pm

UTC+01:00

Location

Cleveland Way National Trail | Saltburn-by-the-sea, EN

Back for our third year! Take on the ultimate adventure - A 109-mile multi-day trek, the full length of the stunning Cleveland Way
Take on the Cleveland Way Challenge where you'll conquer 109 miles of stunning moorland and Coastline, passing some of the most beautiful scenery the UK has to offer!
Starting in Helmsley, you'll trek over 4-consecutive days from Helmsley to Filey. 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 available to hostel room/Shepherds hut)
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
New for 2026: Upgrade from camping to bunk, room or shepherds hut (Where available)*
New for 2026: Tents put up and taken down for you
New for 2026: Daily fresh towels for Enjoy participants and at request on Endeavour & Endure
*Additional costs may vary, please enquire
There are 3 entry categories
ENJOY – Adventure at a comfortable pace with generous cut-offs
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 trekkers that want to focus on the journey, not the load.
Fully supported by the Endurotrek team throughout with baggage transferred and tents put up/taken down each day
ENDEAVOUR – Push your limits
For those wishing to take on a serious challenge and embrace a degree of self-sufficiency.
Participants carry a minimum of 10kg, plus food and water, managing more of your own kit
Ideal for adventurous spirits looking to push themselves — with Endurotrek’s full support team by your side from start to finish. Addiotnal items baggage transfered
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. Carrying all kit and equipment
This is endurance trekking at its toughest. Every step earned, every mile carried, with Endurotrek support always close at hand.
Please NOTE: This is an arduous challenge and not for everybody. You'll be averaging a marathons distance a day, a good level of fitness and desire to push yourself will be required
Whats included in the challenges 🏕️ 🥾
* Expertly Coordinated Challenges: Conquer stunning UK national trails with seamless organisation every step of the journey.
* 3 Nights of Comfortable Camping: Relax at well-equipped campsites with hot showers to recharge for the next day’s trek.
* New for 2026: Upgrade from camping to bunk, room or shepherds hut (Where available)
* Hot breakfast & Daily Packed lunch
* Official Checkpoints: Stay energised with complimentary drinks and snacks at key points along the route.
* Dedicated Medical Support: Enjoy peace of mind with professional assistance on hand throughout the challenge.
* 3 Challenge Categories: Choose a weight that suits your fitness level, from Enjoy, Endeavour or Endure
* New for 2026: Tents put up and taken down
* New for 2026: Daily fresh towels for Enjoy participants
* Baggage Transfers: Walk freely—your kit will be transported to each stop for you if you choose
* Challenge Certificate: Celebrate your incredible achievement with a personalised keepsake of your trek.
www.endurotrek.co.uk