This 14.5-mile section of the Cleveland Way from Kildale to Saltburn starts off in the countryside and ends up by the sea in Saltburn so it is an ideal route to try if you fancy experiencing both the North York Moors and Yorkshire Coast in one walk with a couple of amazing viewpoints along the way.
The length of this route, along with a couple of steep climbs, make this a challenging walk, although it is easy to split it down into more manageable chunks and tackle each section separately.
You can also cover Captain Cook’s Monument to Roseberry Topping in a 7.5-mile circular walking trail which starts and ends in the village of Great Ayton and includes some glorious North York Moors scenery.
Captain Cook’s Monument and Roseberry Topping
Kildale is the starting part for this walk and the peaceful moorland village is home to the lovely St Cuthbert’s Church and a small railway station where you can catch a train through the scenic Esk Valley to the seaside town of Whitby.
Famous Yorkshire explorer, Captain James Cook was born in the nearby village of Great Ayton in 1728 and you’ll start this walk by climbing up Easby Moor to an early 19th-century monolith erected in his honour. There are great views across the North York Moors from Captain Cook’s Monument so it’s worth lingering here to make the most of them.
Great Ayton is also well worth calling in on if you get the time - the River Leven flows gently through the village and the riverside high street includes a selection of shops, pubs and cafes to visit including the excellent Suggitt’s ice cream parlour where you can stop for a treat. There are also two separate village greens where you can enjoy a summer picnic before visiting the Captain Cook Schoolroom Museum to learn more about the sea captain’s early life in Great Ayton.
Walk a few miles further along the Cleveland Way, and the next point of interest is Roseberry Topping, a well-loved peak that’s known as Yorkshire’s Matterhorn due to its distinctive shape that some say resembles a witch’s hat. The hill is just 1,049 feet high so the summit can be reached fairly easily with a 360-degree vista to enjoy from the top. Roseberry Topping is set within beautiful bluebell woods and this part of the Cleveland Way also features the distinctive heather-clad moorland that the North York Moors is famous for. A good place to stop for a rest before tackling the second part of this walk is the King’s Head Inn which lies at the base of Roseberry Topping.
Guisborough Forest, Skelton Beck and Saltburn
In the second section of the walk, you’ll catch your first glimpse of the sea as the Cleveland Way crosses through moorland towards Guisborough Forest. This section of woodland is located high above the market town of Guisborough - the forest is home to an array of wildlife and there are some lovely trails that you can follow through the trees.
This is the pathway to the coast now and after passing by a disused quarry, the landscape mixes between sheltered glades, farmland and villages with some pretty buttercup meadows along the way.
Skelton is one of the last villages you’ll pass through before reaching the coast and the village is home to a distinctive railway viaduct, Skelton Castle country house and Skelton Beck, a stream with attractive stepping stones that ebbs and flows along a woodland valley and down to the sea at Saltburn.
Follow along the path of the stream into Rigg Wood and you’ll reach Saltburn’s lovely Valley Gardens which run parallel to the beck. The Victorian pleasure grounds include colourful flower borders, a maze of walking trails and a miniature railway. There’s also a tearoom where you can relax with a cuppa and cake after completing this section of the Cleveland Way.
Saltburn marks the start of the clifftop coastal section of the Cleveland Way and this elegant seaside town has lots of reminders of its Victorian heyday including a funicular railway - the oldest water balanced cliff lift in the country. This will whisk you from the cliff path down to the beach, sea and historic pier below.
Each July, the town hosts the Saltburn Food Festival with over 100 pop-up stalls selling their tasty wares in Milton Street with live music and special cooking demonstrations. Saltburn is home to an eclectic range of bars and restaurants including:
- Alessi’s - an Italian restaurant and bar
- The Seaview Restaurant - a top choice for freshly caught seafood
- The Sitting Room - a vintage-style tearoom and cocktail bar
- Shanti Cafe - a vegetarian bistro that serves homemade vegan ice cream
- The Ship Inn - a traditional pub with views out to sea
Where to stay
Located close to Great Ayton and the Yorkshire market town of Stokesley, Kirby School Cottage is a beautifully converted holiday home that’s just right for couples and small families. There’s a pretty country garden with a large lawned area and secluded secret seating area that’s accessed through a garden arch.
This elegant cottage is right in the heart of Great Ayton and has open-plan living spaces, French doors that lead into a walled garden and a large master bedroom that features an original fireplace - the perfect place to rest and relax after a challenging Cleveland Way walk.
This three-bedroom cottage is an ideal base for families or groups of friends looking to tackle the Cleveland Way on a walking holiday. Soak in the countryside views from the indulgent outdoor hot tub, whip up a meal in the open-plan kitchen / diner and play some pool and darts in a special games room.
If you're an avid walker and this has piqued your interest, why not browse our full collection of North York Moors holiday cottages and find the perfect place to relax after hiking along this stunning stretch.