Walks in North Yorkshire - 5 of the Best

North Yorkshire encompasses an area of wild heather-covered moorland, historic settlements, fragrant pine forest and a striking coastline under constant bombardment from the North Sea. There are wide open vistas, sleepy villages and miles of coastline to enjoy. In the North York Moors National Park there are over 1,400 miles of walking path to explore with everything from challenging yomps across upland landscapes to gentler options which follow the green valleys.

Historic coastal towns and villages provide a maze of streets to explore and some exciting stories about times past. When the need for refreshment calls, Yorkshire delivers a range of local specialities to tantalise the taste buds from traditional Yorkshire puddings to locally brewed real ales. 

OUR TOP 5 WALKING ROUTES in North Yorkshire

All these routes can be done on our guided and self-guided walking holidays in North Yorkshire. Many other routes also available - three routes of different grade each day to choose from for maximum flexibility and choice. 

1. Grosmont to Whitby

Distance: 7.25 miles (11.6km)
Total ascent: 977 feet (296m)
Estimated walking time: 4 hours 25 minutes

The walk in a nutshell: A linear walk from Grosmont to Larpool Hall in Whitby which follows the tranquil Esk Valley through fields, woods and villages. The route is mostly on fairly level ground on easy terrain.

Don’t miss: Walking across the impressive 13-arch Victorian brick viaduct at the end of the walk.


The start point of the walk is in the village of Grosmont in the valley of the River Esk as it completes its journey to the sea. Grosmont has a rich railway heritage and is the northern terminus of the North York Moors Railway which operates heritage trains between here and Pickering. Grosmont station holds the engine sheds where the steam and diesel locomotives are maintained and restored; it’s a great place to take a peek to see the magnificent machines which revolutionised transport connections at the end of the 19th Century.

Setting off from Grosmont, the route crosses the River Esk, heading briefly north-west, to pick up the main Esk Valley Walk path, one of North Yorkshire’s long distance routes. The symbol for this walk is a salmon – a reminder that the River Esk is used by salmon to travel up from the sea to their spawning grounds. It is the only salmon river in Yorkshire. The path heads north-east over farmland and wooded areas towards the sea; the River Esk and railway line are never far away.

At the oddly named village of Sleights – the old Norse word for flat, level ground - the river has a salmon leap to enable the salmon to make their way up the river over the dam. They are most likely to be seen in the autumn months when they come to spawn but a few may be present at any time of year. 

From Sleights it is a short distance to the pretty village of Ruswarp on the edge of North York Moors National Park. Its main point of interest is its watermill which was originally built in 1752. In 1911 it was severely damaged by fire but was rebuilt and remained as a working mill until 1989. It has now been converted into luxury flats. From here, it is possible to carry on following the Esk Valley Walk into Whitby but our route turns south to go directly back to Larpool Hall via the impressive Larpool Viaduct.

The 120 ft high viaduct used to carry the railway line into Whitby but this was closed in 1965. It is now a walking route over the river and remaining railway line; its elevated position gives sweeping views back up the tree-lined valley and towards Whitby. The viaduct gets a mention in Bram Stoker’s ‘Dracula’ novel!

Having enjoyed the views, it’s a short walk to Larpool Hall to enjoy the Esk Valley from a sitting position, perhaps with a refreshing drink in hand.

2. Cloughton to Robin Hood's Bay

Distance: 10 miles (15.5 km)
Total ascent: 2,050 feet (620m)
Estimated walking time: 5 hours 10 minutes

The walk in a nutshell: A linear walk mainly along the coast from Cloughton up to Robin Hood’s Bay via Ravenscar. Most of the day will be spent enjoying glorious coastal views to the sound of the waves crashing on the beach below. 

Don’t miss: The views along the coast towards Robin Hood’s Bay from the high point at Ravenscar.


The walk starts from the small village of Cloughton which is about a mile from North Yorkshire’s stunning Heritage Coast. The route heads straight towards the sea to join the Cleveland Way – a 110 mile National Trail which runs along the coast and inland to the moors. The route takes us northwards alongside the dramatic and wild coast.

It will become immediately apparent that this is a coastline which is under attack! The geology of soft sandstone and shales means that the daily battering by the North Sea is eroding the cliffs at a rapid rate in many places. This constant erosion means that fresh material is regularly exposed, making it an exciting place for geologists. The rocks here contain the fossilised remains of the plants and animals that lived in the Jurassic period; the keen-eyed might find anything from ammonites to dinosaur footprints!

The first section of the route is through woodland before it reaches Hayburn Wyke (a wyke being the local name for a steep, wooded inlet by the sea). The area is a small nature reserve mainly noted for its ground flora, especially mosses and liverworts. There is a nice view of a rocky cove with its boulder-strewn beach and small waterfall. It’s a picturesque spot, well worth the short detour.

Returning to the Cleveland Way, it’s then left behind for a time with the route heading slightly inland to follow the path of the woods and across farmland. Re-joining the Cleveland Way at Petard point, the trees now left behind, there are sweeping views across the sea and along the coastline in front to enjoy. It’s not unusual to see seals bobbing in the waves below; there is a seal colony just along the coast.

The ground starts to rise and there is a steady walk uphill for several miles until reaching Ravenscar – sometimes referred to as the ‘town that never was’. The settlement is set in a dramatic clifftop location which made it the ideal place for a signal station for the Romans in the 3rd Century. In late Victorian times there were grand plans to expand it to create a seaside resort called ‘Peak’ to rival Scarborough and Whitby. Some roads were built and a handful of fine houses, but the resort never took off, probably due to the long, steep walk down to its rocky beach. The development was abandoned when the developer went bankrupt; today the clifftop hotel is one of the few remaining buildings from this unsuccessful venture. George III was exiled to the house that became the hotel during his periods of madness.

From Ravenscar the route continues along the Cleveland Way with fabulous views towards Robin Hood’s Bay from the elevated position. From here its mostly downhill all the way.

The next point of interest is Boggle Hole, a narrow inlet where the small river of Mill Beck reaches the sea - once used by smugglers. A Boggle (also known as a boggart which Harry Potter fans will be familiar with!), is a hobgoblin – mischievous little people who were purported to live in caves along the coast and in remote parts of the moors.

If the tide is out, it’s possible to walk along the beach to Robin Hood’s Bay to indulge in a spot of beachcombing. If you are lucky you may find a fossil or even some Whitby jet – ancient wood that has become fossilised to form a dark black gemstone which is used to make jewellery and was favoured by Queen Victoria when she was in mourning for Prince Albert.

The walk ends at Robin Hood’s Bay – a small, pretty, historic village made up of tiny fishermen’s cottages which cling to the cliffs. Its harbour once supported a small fleet of fishing vessels but declined in the 1920s with the advent of larger boats which were more economical to run but were too big to use Robin Hood Bay’s tiny harbour. The village takes its name from a Robin Hood – but almost certainly not the one who is associated with Sherwood Forest! Today, many walkers know Robin Hood’s Bay as the end point for Wainwright’s famous 192-mile Coast to Coast Walk.

The village has both tearooms and pubs where you can enjoy some refreshments and reflect on a rewarding coastal walk.

3. Hole of Horcum

Distance: 9.5 miles (15.5 km)
Total ascent: 950 ft (280m)
Estimated Walking Time: 4 hours 50 minutes

The walk in a nutshell: An undulating, linear walk from the ‘Hole of Horcum’ viewpoint across Levisham Moor to the villages of Levisham and Pickering. 

Don’t miss: The splendid views across the Hole of Horcum – a huge, natural amphitheatre carved out of the landscape. In the summer months, the view is enhanced by carpets of purple heather flowers.


The Hole of Horcum has long been a place where travellers have stopped in their tracks to behold the far-reaching views across the brooding moorland scenery. The hole is some 400ft deep and half a mile wide across. It’s a place to drink in the open panoramas and enjoy the sight of rolling grassland and forest which stretch as far as the eye can see. 

Legend has it that the Hole of Horcum was formed when a man who had turned into a giant called Wade, grabbed a fistful of earth to throw at his wife during an argument. He missed and the giant clod of earth formed Blakey Topping, two miles to the east. A more scientific explanation is that it has formed over thousands of years by a process known as spring-sapping. This is where groundwater outflow undermines the slopes above leading them to collapse in landslides which effectively scoop the material away to increase the size of the valley. The process is still continuing today.

Once you’ve had your fill of the views, it’s time to head off round the rim before going down into the ‘Hole’ a little to follow a ridge. There are marvellous views across the wilds of Levisham Moor, an open area of grassland punctuated with large swathes of heather and bracken. The terrain is quite easy – flat and generally firm under foot. 

The walk continues southwards then westwards passing Dundale Pond before reaching a stretch of farmland prior to heading south to reaching the sleepy village of Levisham. Its relatively isolated position means that there is hardly any traffic here. Coupled with the surrounding beautiful scenery, this makes Levisham an idyllic spot. 

Leaving the village, the route follows a track southwards with views down to the railway below – look out for steam trains from the North Yorkshire Moors Railway puffing their way along the valley. Crossing the railway, the path heads up a short but fairly steep wooded hillside and then out onto farmland to eventually reach the town of Pickering. 

Situated at the crossroads of the Whitby to Malton and Ripon to Scarborough roads, Pickering was once an important coaching stop. Naturally, there are a number of medieval inns in the town to provide rest and refreshment to weary travellers!

Having been a settlement since the Bronze Age, Pickering has a rich history. Some of this history is explained in the Beck Isle Museum of Rural Life which is well worth a visit. There is also a Norman church which has some rare and valuable paintings which date back to Norman times and the ruins of a 13th Century castle. There will be time to explore before meeting the vehicle for the return journey to Whitby.

4. Robin Hood's Bay to Whitby

Distance: 8.6 miles (13.8km)
Total ascent: 1,818 feet (551m)
Estimated walking time: 5 hours 25 minutes

The walk in a nutshell: A point-to-point coastal walk from the quaint fishing village of Robin Hood’s Bay back to Larpool Hall in Whitby.

Don’t miss: The beach below Whitby's East Cliff is a good spot to look for fossils, and Whitby jet. Shops in both Whitby and Robin Hood’s Bay sell beautiful jewellery crafted from this gemstone which is actually fossilised ancient wood from trees which were alive in prehistoric times. 


The walk starts in Robin Hood’s Bay, a small fishing village which clings somewhat precariously to sea-ravaged cliffs. The village has a maze of narrow streets which weave past stone cottages that were once homes for a small but hardy fishing community. The number of dwellings here has varied greatly over the years; some 200 have been lost to the sea in times past.

Robin Hood’s Bay was notorious in the 18th Century as being a centre for smuggling activity which was often more lucrative than fishing. It is said that the use of secret passages and connected cellars and lofts meant that goods could travel from the bottom of the village to the top without ever leaving the houses. There will be time to explore this interesting settlement and its small beach before setting off on the walk. The small museum details the history of the village and is well worth a visit. 

Robin Hood’s Bay marks the end point of Wainwright’s famous 192-mile Coast to Coast Walk but this walk is somewhat shorter and in a different direction. Initially the route heads in a north-easterly direction along the Cleveland Way to round the headland before swinging north-west. The views along the coast reveal a wild land of soaring cliffs, wave-cut platforms and hidden bays. There are no more settlements until Whitby. Look out for seals who are often sighted swimming just off shore.

The path passes a lighthouse at Whitestone Point – a reminder that this coast can be treacherous to shipping which strays too close to the shore. Continuing north-west the path finally reaches Whitby, passing one of its most iconic buildings – Whitby Abbey. Perched high above the town, the haunting ruins of what was once a very grand building can be seen for miles around. It’s not surprising that they provided inspiration for Bram Stoker when he wrote his classic book ‘Dracula’ in 1897.

A large part of the ruins that remain are the shell of the 13th Century church of the Benedictine Abbey but the site dates back much further than this. In the 7th Century a monastery was founded here by Hild and became one of the most important religious centres in the Anglo-Saxon world. It was here that the method of calculating the date of Easter was decided – a decision that still holds true today.

Shortly after the abbey are the famous 199 steps which connect it to Whitby town. The streets are packed with shops selling jewellery made from Whitby jet which is found on the beaches in the area, especially after winter storms. The gemstone is deep black and is where the phrase ‘jet black’ originates. It became particularly popular in Victorian times when Queen Victoria wore it during her many years of mourning for Prince Albert. 

The final part of the route weaves through Whitby along the harbour on the banks of the River Esk. Like all harbours, it’s the hub of the town and a great place for watching the world go by. Leaving the town centre you arrive back at Larpool Hall for some well-earned refreshments.

5. Roseberry Topping

Distance: 8.5 miles (14km)
Total ascent: 1,300 feet (400m)
Estimated walking time: 5 hours, 5 minutes

The walk in a nutshell: A point-to-point walk along the escarpment of the North York Moors from Pinchinthorpe to Great Ayton via the viewpoint at Roseberry Topping – dubbed ‘the Yorkshire Matterhorn’. The area was well known by Captain James Cook who spent his childhood here.

Don’t miss: Climbing to the top of Roseberry Topping (320m) for far-reaching views of the North York Moors from its distinctively-shaped top. 


The walk starts from Pinchinthorpe Visitor Centre near Guisborough heading south-east with a small stretch of woodland rising to the right. The path then swings south-west through Hutton Lowcross Woods beneath Hanging Stone – a sandstone outcrop which juts out from the ground above.

The woods give way to Roseberry Common, an open area of moorland punctuated by dry stone walls. Its most notable feature is Roseberry Topping, a strikingly-shaped hill which dominates the landscape. It’s a steep climb to reach the summit (320m) but well worth the effort. The carpet of the North York Moors stretches out for miles around; in August the heather is in flower, turning the landscape into wonderful patches of purple and green. It is said that the young James Cook walked here often and may have been inspired to explore by being able to see land far off in the distance.

Looking south, you can see Airy Holme Farm where Captain James Cook lived from the age of seven for about nine years. His father was a farm worker and when James was older he worked the land here too. One of the greatest explorers of his age came from humble beginnings.

Descending Roseberry Topping by a different route you reach and area which was once used for mining ironstone. Iron was a valuable commodity during the Industrial Revolution so when a seam was found here in the 1870s mining began in earnest. However, a series of setbacks meant that the activity was short-lived with the mine closing in 1881. In 1907 it reopened and became the largest of three ironstone mines in the Roseberry area, feeding the furnaces at Teeside until 1924 when a global recession forced it to close once more. Today you can still see the remains of buildings, spoil heaps and tramway beds.

The walk continues south, skirting along the edge of Great Ayton Moor – classic North York Moors scenery. The route crosses a small road to reach Little Ayton Moor and continues to the high point at Captain Cook’s Monument (324m) on Easby Moor. The 18m (60ft) obelisk was erected in 1827 by Robert Campion - a banker from Whitby - in memory of the celebrated explorer.

Descending the slopes of Easby Moor the route heads north-west along a bridleway until it reaches a small track which goes through the village of Little Ayton and on to Great Ayton.

Great Ayton is where the young James Cook went to school. The Schoolroom Museum is housed in a building which stands on the site of the school that James attended. Great Ayton was also the home of Cook’s parents when they were older. Their cottage was dismantled and shipped to Australia in 1934; a small obelisk stands on the site where it once stood.

Great Ayton’s other claim to fame is its fabulous ice-cream shop. The Suggitt family have been making and selling ice-cream here for several generations. Choose your favourite flavour and enjoy!

North Yorkshire Walking Holiday Options 

All of our guided and self-guided walking holidays in North Yorkshire and the North York Moors stay at our own accommodation - Larpool Hall - home to the World's best fish and chips!

Guided Walking Holidays
in  North Yorkshire
Self-Guided Walking
in  North Yorkshire
Coast to Coast
Guided Trail