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.

Trail running tours available

We also organise trail running holidays along this route. Find out more.

About this route

3 nights
23 miles
Moderate
2nd January to 24th December
Includes Dog-Friendly Tours

From £390 per person

Cleveland Way Short Break

This short break takes in the first stretch of the Cleveland Way along the southwestern edge of the North York Moors. Beginning at the market town of Helmsley, the trail traverses a mixture of wooded dales, open fields and cliff edges, visiting such interesting landmarks as the ruins of Rievaulx Abbey and Roulston Scar, where the head of the Kilburn White Horse can be reached.

After passing through Sutton Bank, the trail follows more clifftops and high moorlands filled with heather, before reaching the stone village of Osmotherley and admiring views over the Gormire Lake below.

The Cleveland Way Short Break

Enjoy a relaxing look at the Cleveland Way Short Break from Helmsley to Osmotherly, taking in fantastic views and wide open spaces. Filmed by Customer Services Supervisor Ben and his walking buddies.
Watch Now

Available tours

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

Short breaks

Code Tour Duration Difficulty Price per person
CLEVWSB From Helmsley to Osmotherley 3 nights, 2 days walking Moderate £390
Contours Walking Holidays Contours Cycling Holidays Contours Trail Running Holidays

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