Cleveland Way
Self-guided walking holidays along the Cleveland Way. Accommodation, luggage transfer and custom holiday pack included.
Cleveland Way
https://www.contours.co.uk/cleveland-way
A self-guided walk around the North York Moors National Park and the Cleveland Heritage Coast.
From £433 per person
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.
Dogs are welcome on select routes along this trail. Look for the pawprint icon when choosing your holiday.
We also organise trail running holidays along this route. Find out more.
From £867 per person
The Cleveland Way spans 111 miles, from Helmsley to Filey. This self-guided walking holiday explores the entirety of the National Trail, from the tranquil beauty of the North York Moors National Park to the bustling fishing ports of the Cleveland Heritage Coast.
There is plenty of spectacular scenery and amazing history to discover along this 109-mile walking trail, with something new to take in at every turn. As the landscape changes from heather-clad moors and green dales to sandy beaches and breezy clifftops, the walk visits a range of old market towns and fishing villages, each boasting their own unique character and warm welcome.
| Code | Tour | Duration | Price per person | |
|---|---|---|---|---|
| CLEVW1 | From Helmsley to Filey | 5 days walking | £867 | |
| CLEVW2 | From Helmsley to Filey | 7 days walking | £1147 | |
| CLEVW3 | From Helmsley to Filey | 9 days walking | £1421 | |
| CLEVW4 | From Helmsley to Filey | 10 days walking | £1558 |
| Code | Tour | Duration | Price per person | |
|---|---|---|---|---|
| CLEVWSB | From Helmsley to Osmotherley | 2 days walking | £433 |
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“Wonderful contrasts of landscapes, and similar to our previous trips, luggage transfers worked well, variety of accommodations appreciated, and a good time had by us.”Ms Miller, USA
“Everything went to plan, even the weather!”Mr Newton, UK
“The variety of landscapes on the Cleveland Way was really nice. The luggage transportation was flawless and the variety of lodging hosts and facilities was terrific. Well done!”Mr McCoy, USA
“Brilliant holiday in every way.”Mr Clipson, UK
“Excellent choice of stays.”Mr Hallatt, UK
“Thanks for the excellent arrangements. Wonderful walk - lucky with weather - no rain! Hope to be fit enough for another trail!”Mrs Gambier, UK
“This was the best long distance trail to date that I have had the pleasure of walking. The scenery was amazing – countryside, moorland and coast all in one package. Challenging in places but doable.”Mr Wilson, UK
“Good weather, lovely scenery and paths, niggles in taxi arrangements but overall a lovely holiday. Lovely gentle rolling wolds, very well signed, quiet.”Dr Chatfield, UK
“Wonderful scenery, great variety of terrain, interesting towns and villages on the way. Accommodation varied but overall good.”Mrs Wood, UK
Dog friendly