Cleveland Way

Cleveland Way

A self-guided walk around the North York Moors National Park and the Cleveland Heritage Coast.

3 to 11 nights
23-111 miles
Moderate to Strenuous

From £390 per person

Find your holiday

About the trail

Take a self-guided walking holiday along the Cleveland Way, a walk of stunning contrasts. Beginning in the old market town of Helmsley, the Cleveland Way traverses the western escarpment of the North York Moors to the coast at Saltburn-by-the-Sea, before following the Cleveland Heritage Coast to the Victorian town of Filey.

While walking through the Moors, the trail traverses woodland, green dales and heather moorland. This section is packed with historic interest, including the iconic White Horse of Kilburn. The coastal section then follows high cliffs, sandy bays and wooded wykes. Picturesque fishing villages pepper the trail, as well as the famous port of Whitby. Overall, the Cleveland Way is an incredible walking trail filled with intrigue and beauty.

We offer multiple holiday options along this trail. If you wish to experience the entire trail, simply select the first option from the list below.

Choose your route

  • This route includes dog friendly tour options Cleveland Way
  • This route includes dog friendly tour options Cleveland Way - Moors Section
  • This route includes dog friendly tour options Cleveland Way - Coast Section
  • This route includes dog friendly tour options Cleveland Way Short Break

Dog friendly tours available

Dogs are welcome on select routes along this trail. Look for the pawprint icon when choosing your holiday.

About this route

6 nights
58 miles
Moderate
2nd January to 24th December
Includes Dog-Friendly Tours

From £735 per person

Cleveland Way - Moors Section

The North York Moors section of the Cleveland Way begins in Helmsley and takes in the UK’s largest expanse of heather moorland on route to Saltburn-by-the-Sea. The historic landmarks of Helmsley Castle and the ruins of Rievaulx Abbey are just some of the amazing sights nestled among beautiful surroundings here.

The breath-taking viewpoints of Sutton Bank and Roseberry Topping are worth pausing at to admire the views, while the many quaint settlements along the way offer warm welcomes and insightful history to explore at your leisure.

Available tours

Code Tour Duration Difficulty Price per person
CLEVWM From Helmsley to Saltburn-by-the-Sea 6 nights, 5 days walking Moderate £735

Short breaks

Code Tour Duration Difficulty Price per person
CLEVWSB From Helmsley to Osmotherley 3 nights, 2 days walking Moderate £390

Customer reviews from the Cleveland Way - Moors Section

“5 similar distance walking days, with extensive views throughout, blessed for the most part by dry, sunny weather. Well organised, as always. We've been using Contours every year since 2010!”
Mr Parkinson, UK
“For most of the walk I just had sheep and Grouse for company. It was isolated and beautiful.”
Mrs Davies, UK
“I found the walk very interesting particularly the views across to the Pennines. I found the selection of B&B's very good and would certainly recommend your company to others.”
Mr Wood, UK
“Beautiful scenery. Certainly an undulating walk, strenuous in parts. Very helpful to have roughly equal distances each day. A very interesting five-day walk in beautiful countryside.”
Mr Donnelly, UK
“A brilliant walk arranged by yourselves of course and helped by perfect walking weather, all the accommodations were good. Once again thanks for a great holiday and let us know when we need to book for next April.”
Mr Bottomley, UK
“I appreciated the efforts made to cut down the daily mileage- my husband managed well and thoroughly enjoyed the holiday.”
Ms Angus, UK
Find your holiday