The first part of the Cleveland Way starts in Helmsley and after a journey of ten and a half miles, finishes at the visitor centre in Sutton Bank. The route climbs gradually out the wooded valley of the River Rye to reach the escarpment of the Hambleton Hills at Sutton Bank.
The route forms an easy introduction to the Cleveland Way as it uses clearly marked paths through woodlands and open fields.
If you are walking the complete route of the Cleveland Way to Filey, you’ll pass very close to Rievaulx Abbey, Byland Abbey, Mount Grace Priory, Gisborough Priory, Whitby Abbey and Scarborough Castle all under the care of English Heritage.
This section of the Cleveland Way is covered by the Explorer OL26 Ordnance Survey map. The map displays the western area of the North Yorkshire Moors, the Cleveland Hills, and a section of the Howardian Hills. With this map, you also get a code for use on your iOS or Android smartphone or tablet. The OS Explorer map for the North Yorkshire Moors – Western Area is available in both the standard paper version and weatherproof ‘Active’ version.
Helmsley is on a number of bus routes. It is accessible from Malton, York, Pickering and Scarborough.
A number of other walks finish/start in Helmsley. The Tabular Hills Walk runs from Scalby Mills on the Coast. The Ebor Way follows a gentle route to Ilkley and passes through York. Finally, Helmsley is the start/finish of The Inn Way which is a circular walk around the North Yorkshire Moors.
Helmsley is a pretty market town full of quaint little shops and dominated by the ruins of Helmsley Castle. English Heritage manages the castle and it is worth a visit before you start your walk. If you are an English Heritage member you can enter the Castle for free.
Sutton Bank, by contrast, is pretty much inaccessible by public transport, except in summer on a Sunday, when the Moorsbus runs between Helmsley and Sutton Bank. So if you are walking the whole route in sections (as I did) you’ll need a lift from Sutton Bank or a fairly expensive taxi ride. If you are walking the whole route there are very few options for B&B around Sutton Bank.
Helmsley to Rievaulx Bridge
From the Market Cross in Helmsley Market Place follow the road signposted to Stokesley. Walk past All Saints Church and then turn left onto the road called Cleveland Way, follow the sign “Footpath to Rievaulx”. Walk towards the car park at the end of the road. At the side of the car park is a stone sculpture that marks the beginning of the Cleveland Way. Follow the clear track at the side of the sculpture.
Leaving Helmsley the path rises gently upwards with some nice views back towards Helmsley and across Ryedale. After crossing several fields through kissing gates the path takes a sharp left turn. It then runs alongside Blackdale Howl Wood which grows on the north bank of the River Rye.
The path eventually drops down into the wood using a number of stone steps. Climbing back up out of a small wooded valley the woods open out briefly near Griff Lodge. Close by are the ruins of the Medieval village of Griff. The village is mentioned in the Doomsday Book of 1086. It was thought to have been abandoned after the Black Death.
The path enters Whinny Bank Wood and follows a clear track through the wood. It finally emerges out of the wood onto a metalled road. Turn left here to follow the path at the side of the road to arrive at Rievaulx Bridge. The Cleveland Way continues over the bridge.
The ruins of Rievaulx Abbey are a short walk away down the road to the right. Rievaulx Abbey is certainly worth a visit if you have time. It is probably the finest abbey in the area. English Heritage looks after the Abbey and if you are a member you can enter for free. See my guide to Rievaulx Abbey for more information.
Rievaulx to Cold Kirby
Continue over Rievaulx Bridge along the road, signposted to Scawton. At a road junction near the white barn carry straight on. Rather confusingly, the road to the right is signposted to Cold Kirby, but that is not our route.
Follow the road to a fingerpost (see photo at the top of the article). Turn right here to follow a gravel track running alongside a wood on the left and a number of fishing ponds on the right. The route then crosses over some stepping stones towards a track. Turn right onto the track which goes through a forested valley.
At a junction of tracks turn left to walk into Flassen Dale. Walk along the Dale and then turn right up a less distinct path into a wooded valley. The path climbs slowly through the woods and after passing through a stile leaves the wood onto open farmland.
Follow the track for some distance to some farm buildings. Turn right after the buildings along the signposted path to reach the tiny village of Cold Kirby.
Cold Kirby to Sutton Bank
Once you’ve got onto the main road through the village, walk up to the top end. Turn left just past the last house and follow a track through fields. Continue along the track as it turns right to go alongside a wood. Pass through some farm buildings and continue on through the woodland.
At this point, the path follows a well-signposted diversion. Continue through the woods until you reach a wooden footbridge. Cross this bridge to arrive at the Sutton Bank Visitor Centre.
Sutton Bank to Kilburn White Horse
This part of the walk is a circular detour and well worth the effort. The path is on the other side of the A170, which is very busy so cross carefully. As you walk from Sutton Bank to the White Horse the view changes gradually. It starts with the Pennines, then to the Plain of York and finally out over the Vale of Pickering towards the Yorkshire Wolds.
The path passes the Yorkshire Gliding Club so if you are lucky you might see a glider or two, taking off or landing.
From the path above the White Horse, the whole of the Vale of York lies in front of you. On a clear day it is possible to make out the towers of York Minster and the cooling towers of the power stations near Doncaster. Look west and you can see the white domes of the listening station at Menwith Hill above Harrogate.
The Victorian landmark, the White Horse itself, is visible for miles around. The figure is 96m wide and 69m high. It was the work of John Hodgson a local schoolmaster who organised its construction in 1857. The horse was carved out of the topsoil and the exposed scree underneath whitewashed. The view of the horse from the top is quite poor and a much better view can be obtained by descending the path down to the picnic area at its base.
To continue on the Cleveland Way return along the path you’ve just walked on, back to Sutton Bank. The Cleveland Way continues from the Visitor Centre on the next leg towards Osmotherly.
Want to save this for later? Pin the image below!