Cleveland Way

Cleveland Way

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 £320 per person

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.

Dog friendly tours available

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

"Along the Trail" by Sam Cockerham (2021)
"At the finish line" by Sam Cockerham (2021)