Cleveland Way: Kildale to Guisborough Woods


General Data

Initially the trail leaves Kildale via a steeply-climbing road; when this is left, a more gradual ascent through woodland leads to a summit by Captain Cook's Monument on Easby Moor. A descent follows to a road, after which a steep but shorter climbs leads up onto Great Ayton Moor. A gradual climb then follows to the northwestern tip of the moor.

Here there is a short but rewarding diversion; the trail descends steeply down to the west, crossing Roseberry Common before climbing to reach the summit of Rsoeberry Topping, from where magnificent views unfold in virtually every direction. Sadly that same climb has to be repeated in the other direction to return to Great Ayton Moor.

The trail then heads east along the edge of the moor, descending before down to Black Nab before climbing once more. Soon the views disappear as it enters Guisborough Woods, immediately to the south of the town of Guisborough.

Distance  7 miles
Ascent  1722 feet
Descent  1316 feet
Est. time  3 hours 51 minutes
Difficulty  medium

Map of the leg

Maps courtesy of Google Maps. Route for indicative purposes only, and may have been plotted after the walk. Please let me have comments on what you think of this new format.


This leg starts off at a triangular road junction with Station Road in the hamlet of Kildale at NZ607093. At the junction, turn left down Station Road, and after passing some cottages on the right, turn right down another road. This descends downhill, curving to the left to pass under a railway bridge at NZ606096, and then crosses a bridge over a stream.

Follow the road to a cattle grid, after which it starts climbing uphill in a rough northerly direction. it passes Bankside Farm on the right and some barns on the left to reach a clapper gate beside a cattle grid. The ascent starts to slacken three-quarters of a mile after the railway bridge. On a right-hand bend at the crest of the hill, turn left to join a gravel track that goes through a gate to enter woodland.

Follow the track westwards; when the track curves to the right after a fifth of a mile, turn left to follow a footpath through the trees. The path passes a stile and continues on as the tip of Captain Cook's Monument becomes visible ahead. After leaving the trees the path climbs steeply up stone steps. Go through a gap in a stone wall and continue uphill across moorland to reach the monument at NZ590101.

At the monument turn right to follow a flagstone path northwards. It descends across the moors and becomes a gravel path that heads downhill through trees. After half a mile it goes through a pedestrian gate beside a field gate to reach Dikes Lane at NZ591110. Turn right for a few yards to pass a car park on the right, and then turn left. Ignore a larger track angling off to the right, and instead take a footpath that heads up steps to the north. When the steps end a more gradual ascent continues, following a fence and then a wall on the left. Continue along this path until a pedestrian gate is reached at NZ587127, 0.9 miles after the road.

Here the trail makes another official diversion to visit the outlying summit of Roseberry Topping which lies half a mile to the west. Go through the pedestrian gate and turn left down some steps. Eventually the gradient slackens; continue on with a wall on the left to reach the base of Roseberry Topping. More steps and a steep zigzagging path lead up to reach the craggy summit at NZ579125. Once there, descend off the hill by the same route and climb the steps back up to reach the pedestrian gate and the main Cleveland Way route.

Three paths radiate out from the gate across the moorland; take the middle path that heads eastwards; do not take the path that runs along the wall on the left or the one beside the trees on the right. This path climbs a slight summit before falling to reach a bridleway gate. Go through this gate to join a track and then turn right along this track. It immediately curves to the left and continues falling with forestry on the left. Go through a vehicle barrier and then turn right along another track to reach a bridleway gate beside a field gate.

Go through this, pass another vehicle barrier and continue uphill. After a couple of hundred yards turn left to join a narrow footpath that heads across the moorland. The path curves to the left and the right as it descends, joining a fence on the left. It crosses a rough, reedy area with flagstones across boggy sections before starting to climb alongside a wall, passing Highcliffe Farm on the left. Go through a bridleway gate through a fence near the farm and continue climbing. The wall and path both curve to the left, aiming for trees ahead. Ignore a gate off to the left, and shortly afterwards turn left through a clapper gate to enter Guisborough Woods near Highcliff Nab at NZ611135.


Places of interest

Kildale, its station and the railway line

Kildale is a small hamlet nestling on the northern flanks of the North York Moors. It has a church, a tearooms, and a railway station on the Esk Valley line.

The Esk Valley railway runs from Middlesbrough to Whitby; it is all that remains of a network of railway lines across North Yorkshire, including the preserved North Yorkshire Moors Railway. The stretch of line between Battersby (a little way west of Kildale) and Grosmont was built by the North Yorkshire and Cleveland Railway, a short-lived affair that opened in 1858, but which was soon taken over by the North Eastern Railway. It seems slightly odd that this lengthy, remote line, whose only large settlement is Whitby, survived the Beeching Cuts. But locals must be glad that it was.

location UID #339

Captain Cook’s Monument, Easby Moor

Captain James Cook, the ‘discoverer’ of Australia, has obvious connections with the sea. It’s therefore slightly odd that a monument to him is found on top of a hill on Easby Moor, nine miles from the sea.

James Cook was born in the Yorkshire village of Marton in 1728, but moved as a child to the village of Great Ayton, which is in the monument’s lee and explains its location. The monument itself is a squat obelisk, but the commanding views more than reward the climb up to it.

location UID #340

Roseberry Topping

Roseberry Topping is a conical hill in North Yorkshire, separated from the nearby moors to the east by a saddle. It offers commanding views over the North Yorkshire plains to the west as far as the Pennines, and an official spur from the Cleveland Way heads off to the summit.

Until 1912 the hill had a different shape, before ironstone mining at its western end, potentially combined with a geological fault, caused that end to slump. It is a hill whose shape varies radically depending from where it is viewed; sharp-nosed from one angle, conical from another.

The young James Cook – later the explorer Captain Cook – lived nearby as a child, and would regularly climb the hill. Perhaps this gave him his first taste of exploration, an endeavour that would make him famous and ultimately cost him his life.

location UID #341


Guisborough is a small market town in Cleveland, inland from the coast and southeast of Middlesborough and the River Tees, nestling on the northern flank of the North York Moors. It expanded massively after the Second World War in conjunction with the expansion of the nearby steel and chemical works. Despite this it sill hold a lively twice-weekly market.

It had no rail station; the Middlesborough and Guisborough railway opened in 1853 and closed in 1964. The town does have regular bus services to many locations, including Middlesborough, Whitby, Scarborough and Redcar.

location UID #342


Kildale has a station on the Esk Valley Line which runs between Middlesborough and Whitby. See the National Rail website for more information.

Kildale is also served by a couple of buses to Stokesley every day.

There is no public transport serving Guisborough Woods. However the centre of the town of Guisborough lies a mile to the north, from where regular bus services run to Middlesborough and Whitby.

For more public transport information, see the Travelline website.

Map information

Landranger (1:50,000)   Outdoor Leisure (1:25,000)
Landranger 93 (Middlesbrough, Darlington & Hartlepool)
Landranger 94 (Whitby & Esk Dale, Robin Hood's Bay)
Outdoor Leisure 26 (North York Moors - Western Area)

Photos of this leg

Houses in Kildale.A John Wesley memorial in Kildale.Bankside Farm.The path heading west through the Coate Moor Woods.The Captain Cook Monument on Easby Moor.The view from the Captain Cook Monument on Easby Moor.The view from the Captain Cook Monument on Easby Moor, showing the terrain walked over yesterday.The view from the Captain Cook Monument on Easby Moor towards Roseberry Topping.The descent north off Easby Moor.The view back over Easby Moor from the climb onto Great Ayton Moor.The climb onto Great Ayton Moor.The view back over Easby Moor from the climb onto Great Ayton Moor.The path across Great Ayton Moor.The descent towards Roseberry Topping from Great Ayton Moor.Roseberry Topping summit.The view from Roseberry Topping summit towards Great Ayton Moor.The view from Roseberry Topping summit.The view from Roseberry Topping summit towards Great Ayton Moor.The view back up Roseberry Topping. Lookinbg west across Newton Moor.The boggy area of ground near The Race.Highcliff Nab.

Accommodation information

Percy Rigg Farm
North Yorkshire
YO21 2SD
P: 01642 724159

Grid ref: NZ629102 (54.483261,-1.030867)
Oak Tree Farm
North Yorkshire
YO21 2RU
P: 01642 722511

Grid ref: NZ602111 (54.491746,-1.071661)
King's Head Hotel
The Green
Nr Great Ayton
P: 01642 722318

Grid ref: NZ571130 (54.509124,-1.119812)
Royal Oak Country Inn
High Street
Great Ayton
North Yorkshire
P: 01642 722361

Grid ref: NZ563107 (54.488442,-1.133078)
Bridge Guest House
5-9 Bridge Street
Great Ayton
North Yorkshire
P: 01642 725236

Grid ref: NZ557107 (54.488585,-1.141626)
Susie D's Bed and Breakfast
116 Newton Road
Great Ayton
North Yorkshire
P: 01642 724351

Grid ref: NZ563115 (54.495564,-1.131718)
The Fox Inn
Bow Street
North Yorkshire
TS14 6BP
P: 01287 632958

Grid ref: NZ615160 (54.535505,-1.050691)
The Three Fiddles
32 Westgate
North Yorkshire
TS14 6BA
P: 01287 632417

Grid ref: NZ614160 (54.535263,-1.052966)
Gisborough Hall Hotel
Whitby Lane
North Yorkshire
TS14 6PT
P: 0844 8799149

Grid ref: NZ625163 (54.538482,-1.036041)
Back to  Bloworth Crossing to KildaleForward to  Guisborough Woods to Saltburn

Trails Index  Back to 'Cleveland Way' index
Trails Index  Back to Trails index