Circular and Linear Walks

A coastal view from the Cleveland Way

Circular and Linear Walks

This  circular walk takes in the majestic heights of Roseberry Topping.  An iconic feature, seen for miles from much of North Yorkshire and Cleveland, its distinct form gives it the nickname of the Yorkshire Matterhorn. It was also voted the 6th most Romantic place in the World to propose in the World Travel Awards!

This is the land where the famous explorer Captain Cook grew up and you will see reminders of him in many places, not least at Captain Cooks Monument on Easby Moor.  There are some real delights to this walk as it wanders through woodlands and across heather moorland.

  • Distance:  7.3 miles (11.7km)
  • Duration:  allow 5 hours including breaks
  • Difficulty:  This is a strenuous walk with some steep climbs

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It might only be a shade under 3 miles, but this is a real adventure walk for all the family, with some awe-inspiring views into the bargain.  There's a striking panorama of Middlesbrough, the Cleveland plain, Roseberry Topping and Cook's Mounument, and you'll get amazing views both on the outward leg and then - after a stiff, stepped climb - on the return section that follows the Cleveland Way National Trail across Cringle Moor.  The start of the trail is in the privately owned Lord Stones Country Park, where there's access to the ancient stone that gives the walk its name - as well as parking, a cafe-restaurant and local produce shop.

* Distance:   2.75 miles (4.4km)

* Duration:   2 hours

* Difficulty:   Moderate - its a short walk but it does include a big up and down

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Part of the Try a Trail series, here is a perfect walk for a weekend.  It follows the northern escarpment of the Cleveland Way from Kildale through to the sea at Saltburn.  The recommended overnight stop is at Guisborough. There are many highlights to the route, including Captain Cooks Monument, Roseberry Topping, Gisborough Priory and the delightful seaside settlement of Saltburn by the Sea.  There are also great rail connections to both ends at Kildale and Saltburn via Middlesbrough.

  • Distance:  16.6 miles (26.7km)
  • Duration:  Two day walk - Day 1 about 5 hours and Day 2 also about 5 hours
  • Difficulty:  This is a moderate walk

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This is a fantastic two day walk taking in the jewels of the North Yorkshire Coast.  Take a weekend to explore this superb section of the Cleveland Way starting from Whitby and travelling  to Scarborough, with an overnight stop at the enchanting village of Robin Hood's Bay.  There are endless highlights to this route, the cliff scenery, Whitby Abbey, Ravenscar and the rocky cove of Hayburn Wyke to name but a few.

  • Distance:  20.8 miles (33.5km)
  • Duration:  Two days - Day 1 about 5 hours, Day 2 about 8 hours
  • Difficulty:  Moderate - there are plenty of ups and downs along this walk

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Explore handsome Osmotherley and its surroundings on a 3¼ -mile circular walk that touches every aspect of the village’s rich religious past. The village itself has both medieval church and 18th-century Methodist chapel, while following field and woodland paths to the northwest leads to the impressive ruins of Mount Grace Priory – the best-preserved Carthusian remains in the country. Returning to Osmotherley along a section of the Cleveland Way National Trail, there’s the option of calling in at The Lady Chapel, a place of Catholic pilgrimage for over 600 years – beautifully set on a hillside with sweeping views over Bilsdale, Teesside and the Pennines. Osmotherley is a noted walking centre – on the Cleveland Way and at the start of the Lyke Wake Walk – so there’s no shortage of places to rest up afterwards, including three pubs for a population of just a few hundred!

  • Distance:  3 1/4 miles
  • Duration:   3 hours
  • Difficulty:     a moderate walk, with a drop to reach Mount Grace Priory and the return climb back

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This short circular walk  is a great way to appreciate the moorland fringe of the North York Moors National Park. Starting from Square Corner it descends on an attractive stone slab path to reach the delightful village of Osmotherley. This picture postcard village has been welcoming holiday makers and day trippers for over a hundred years and has good facilities with several pubs and cafes.  Further on the walk climbs back onto the moors, taking in a length of the historic Hambleton Drove Road.

  • Distance: 4.8 miles (7.8km)
  • Duration: allow 3 to 3 1/2 hours including breaks
  • Difficulty:  Moderate

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This is a circular walk on an attractive coastal section of the Cleveland Way at Ravenscar.  Ravenscar is a great spot to visit, with a unique history - it is known as the "Town that never was" and outstanding views across the coast to Robin Hoods Bay. It also houses the National Trust Visitor Centre, where there is plenty of good advice and drinks and light snacks are available, as well as the Ravenscar Tea Rooms and Raven Hall Hotel

This is a  walk of great contrasts. Firstly the dramatic cliff top experience, then a chance to walk on the old railway line between Scarborough and Whitby before culminating in a visit to the fascinating site of the Peak Alum Works.

  • Distance:  6 miles (9.5km)
  • Duration:  allow 3 1/2 to 4 hours including breaks
  • Difficulty:  this is a fairly easy walk

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Enjoy the National Park in a nutshell on this 11-mile walk through some of the North York Moors’ most characteristic landscapes. From the craggy heights of Ravenscar the route runs across Howdale Moor for some classic moorland scenery before dropping down to the old Scarborough-to-Whitby railway line and along to the famous smugglers’ haunt of Robin Hood’s Bay. Both here and at nearby Boggle Hole you can indulge in a spot of rock-pooling and fossil-hunting, before returning along an exhilarating clifftop stretch of the Cleveland Way National Trail, via the old alum works industrial site. That’s a powerful combination of the best National Park experiences in one big day out.

  • Distance: 11 miles (17.7km)
  • Duration:  6 1/2 hours
  • Difficulty:  This is a strenuous walk

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This 6 mile circular walk to Maw Wyke follows the cliffs north of Robin Hood's Bay and passes Ness Point, one of the most treacherous headlands along this coastline. Looking at the jagged rocks, it's not hard to imagine small fishing boats being tossed about at the mercy of the sea.  The stiff breezes, wheeling seabirds and clifftop panoramas are left behind on the return along the Cinder Track, the line of the old railway between Whitby and Scarborough, where occasional benches, hedgerows and wildflower patches offer a gentle approach to the age-old fishing village of Robin Hood's Bay.

  • Distance    6 miles (9.8Km)
  • Duration     4 hours
  • Difficulty      Moderate - it is generally easy going, but there is one steep climb to get from the Cleveland Way to the Cinder Track

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Get some sea air on this 4-mile circular walk, starting at the atmospheric old fishing village of Staithes, with its harbourside cottages, cobbled streets and winding alleys. Leave the sheltered harbour and follow the Cleveland Way National Trail for the first half of the walk, tramping across the high cliffs to Port Mulgrave and enjoying wonderful coastal views. The return is across fields and through woodland, via the small hamlet of Dalehouse.

  • Distance: 4 miles (6.4km)
  • Duration:  2 1/2 hours
  • Difficulty:  A moderate walk, wit a steep climb from Staithes Harbour to the cliff top and a descent and ascent in the woods.

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Where to stay, great days out & lots to do!