Cleveland Way Run

Cleveland Way Run

A trail running holiday through the North York Moors and along the Cleveland Heritage Coast, from Helmsley to Filey.

3 to 8 nights
42-111 miles
Easy / Moderate to Strenuous

From £400 per person

Find your holiday

About the trail

High open moorland and breezy coastal running await on the Cleveland Way, a trail running holiday of two distinct halves. From Helmsley, delve through the North York Moors National Park. Here the route hikes to its highest point at Roseberry Topping, but it’s suitably apologetic with smooth, pleasant trails and great views over purple moorland. Soon you’ll take on the North Yorkshire and Cleveland Heritage Coast, where you’ll spy sandy beaches from hilly cliff-top trails. Top up your reserves with a seaside fish and chips and press on to the route’s end in Filey. It’s a scenic, refreshing run with some challenging gradients.

Choose your route

  • This route includes dog friendly tour options Cleveland Way Run
  • This route includes dog friendly tour options Cleveland Way Short Running Break

Dog friendly tours available

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

Walking tours available

We also organise walking holidays along this route. Find out more.

About this route

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

From £400 per person

Cleveland Way Short Running Break

This fantastic short break explores the stunning Cleveland Heritage Coast section of the Cleveland Way National Trail, beginning in the Victorian seaside town of Saltburn-by-the-Sea and following the rugged cliffs down to Scarborough.

The Cleveland Way Short Running Break is a classic showcase of breath-taking coastal terrain, bounding along bracing clifftops, racing across sandy beaches and exploring a range of picturesque fishing villages and bustling seaside resorts. 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 heritage and folklore, and the seaside resort of Scarborough, with its ancient castle providing panoramic views over the Yorkshire coastline. This three-day run, filled with beautiful landscapes and a wealth of maritime and literary history, is a fantastic way to experience this short section of the Cleveland Way.

Available tours

Code Tour Duration Difficulty Price per person
R-CLEVWSB From Saltburn-by-the-Sea to Scarborough 3 nights, 2 days running Moderate £400