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

4 to 7 nights
53 miles
Moderate to Demanding / Strenuous
2nd January to 24th December
Includes Dog-Friendly Tours

From £515 per person

Cleveland Way - Coast Section

The Heritage Coast Section of the Cleveland Way begins in the Victorian seaside town of Saltburn-by-the-Sea and follows the rugged cliffs to Filey. While the scenery throughout is beautiful, some of the best views can be seen from Boulby, the highest cliffs in England.

Locations of particular interest include Whitby, boasting amazing history, heritage and folklore, and the seaside resort of Scarborough, with its ancient castle providing panoramic views over the Yorkshire coastline. This walk, marked by picturesque fishing villages and with a wealth of maritime and literary history, is a fantastic part of the England Coast Path.

Available tours

Code Tour Duration Difficulty Price per person
CLEVWC1 From Saltburn-by-the-Sea to Filey 4 nights, 3 days walking Demanding / Strenuous £515
CLEVWC2 From Saltburn-by-the-Sea to Filey 5 nights, 4 days walking Demanding £635
CLEVWC3 From Saltburn-by-the-Sea to Filey 6 nights, 5 days walking Moderate £755
CLEVWC4 From Saltburn-by-the-Sea to Filey 7 nights, 6 days walking Moderate £875

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 - Coast Section

“One of the best holidays we have had. Accommodation, owners, directions and locations all perfect. Many thanks. We will be using Contours again.”
Mr Pickup, UK
“In an itinerary that is complex and involving the schedule we experienced, it was very satisfying to see the whole experience well organised and your pack and information worked extremely well... I would use your services again. Overall, every accommodation provider... had a great welcome and their staff were all very good, friendly, attentive and very personable. Covid procedures were in all cases well documented and executed. Some places were more rigorous than others but we were very pleased to comply and conform, it gave us a feeling of confidence in the accommodation.”
Mr Perry, UK
“The scenery was beautiful at every turn and the weather a huge bonus (t-shirt and shorts weather late September) Having our baggage transferred each day was great and the variety of B & Bs we stayed in was interesting. Each day's walking featured different highlights.”
Mrs Simpson, UK
“Staithes, Robin Hood's Bay, Scarborough and Filey all delightful, and Contours served us typically well with accommodation, seemless luggage transfers, and flexibility when needed.”
Mr Jarvie, UK
“Superb stretch of coastline and all the arrangements worked out well.”
Mr Simmons, UK
“Thoroughly enjoyed walking the Cleveland coast and lots of beautiful towns/villages.”
Mr Baker, UK
“The holiday arrangements worked very smoothly with the baggage transfer, route details and selected accommodations. I would highly recommend this company for your dog friendly walking holidays.”
Miss Wilkinson, UK
“A lovely coastal walk with accommodation and luggage transfer well organised.”
Mr Pearson, UK
“Stunningly beautiful walk, very enjoyable, would do it again.”
Ms Unwin, UK
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