Five walks to try on the Cleveland Way National Trail - Gorgeous Cottages
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Five walks to try on the Cleveland Way National Trail

Did you know that the Cleveland Way is one of seven National Trails in England? What’s more this stunning walking route celebrates its 50th birthday in 2019.

Enjoy a coastal walk in the North York Moors

Starting in the market town of Helmsley, the Cleveland Way passes through the North York Moors National Park with landmarks like the White Horse at Kilburn, the Wainstones and Roseberry Topping to spot along the route. It then heads along the clifftop paths of the gorgeous Yorkshire Coast – all the way from Saltburn to Filey.

5 of the best walks to try on the Cleveland Way

Image by Chris Parker

It’s 109 miles in total but there’s a selection of shorter routes to try along the way. Take a look at some of our favourites walks and start planning your next visit!

#01 Follow in the footsteps of Captain Cook

Roseberry Topping and the Bluebells by Colin Carter

Image by Colin Carter

Famous explorer Captain James Cook spent his childhood in the Cleveland Way village of Great Ayton and you can follow in his footsteps by walking from here up Roseberry Topping. This distinctive hill is a family favourite and there’s even a great dog-friendly pub at its base. You can combine the walk with a visit to Cook’s Monument which was erected on Easby Moor in 1827.

#02 Take a walk along the coast

Staithes is one of the villages along the Cleveland Way Coast Line

Much of the Cleveland Way National Trail is along the gorgeous Yorkshire coastline and there are plenty of lovely fishing villages (and towns) to call in along the way including Staithes, Sandsend and Runswick Bay.

Images of Yorkshire - Robin Hoods Bay

One of our favourites is Robin Hoods Bay and we love to walk along the Cleveland Way clifftops from Whitby.

#03 Enjoy the views from highest point

Urra Moor is the highest moor in the North York Moors (1454 feet above sea level) so you’ll get spectacular views from here. You can combine a walk to Urra Moor with a visit to the Wainstones – a dramatic rock formation which you can scramble up if feeling adventurous.

#04 Spot the Kilburn White Horse

Five walks to try on the Cleveland Way

The view from Sutton Bank in the North York Moors has got to be one of the finest around. It’s also home to the Sutton Bank National Park Centre which includes an adventure playground and gift shop so is a great walk for families with children to try.

It’s just a short walk from Sutton Bank to the Kilburn White Horse – one of the most famous landmarks in the North York Moors. This whopping turf cut figure is 314 feet by 228 feet and dates back to 1857!

#05 Visit a historic castle and abbey

The Cleveland Way starts in Helmsley and there’s several walks to try around here. We recommend heading to Helmsley Castle and walking along the Cleveland Way National Trail to nearby Rievaulx Abbey.

Things to do Helmsley

Both are National Trust sites that date back to the 12th century so there’s lots to explore and you’ll also pass the beautiful Helmsley Walled Garden along the way.

Where to stay

If you are planning to explore the Cleveland Way National Trail in 2019, Gorgeous Cottages have a range of holiday cottages throughout the North York Moors. For help and advice give us a call on 01642 263 249.

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