Cleveland Way

Three quite different kinds of walking before the moors proper. Out of Helmsley it is Rye valley farmland and steep-sided broadleaf woodland, with stepped paths through the trees that go greasy after rain, past Rievaulx and up Nettle Dale on firm farm tracks. At Sutton Bank the ground tips over onto the limestone escarpment and stays on the lip of it, soft grass along the top of a long drop with the Vale of York laid out to the west. Beyond Sneck Yate the trail joins the Hambleton Drove Road, a broad old droving track that gives the fastest and easiest miles on the whole route, until the descent off Black Hambleton runs onto a loose, rock-strewn track that is genuinely unpleasant underfoot, and the drop into Oakdale adds lichened stone steps that are slick when damp. Osmotherley is the last village with a full range of services before the escarpment. After it the character changes again onto Scarth Wood Moor, the first open heather of the trail, then down through woodland into Scugdale.

Logistics: Nothing on the escarpment between Sutton Bank and Osmotherley is on a through road, so the middle of this stretch commits you for around 18 km once past the Sutton Bank car park. The one staffed stop inside that stretch is the tea room at High Paradise Farm, about 19 km in, which the trail runs straight through. High Paradise's own site says the tea room is on the Cleveland Way and can be reached on foot, bike or horse only, and gives its hours as Thursday to Sunday from March to the end of September, weekends only from October to the end of December, and every bank holiday Monday, 10am to 4pm, with hot food from the kitchen between 12 and 3 and drinks and cakes after that. It says it takes no bookings and asks a £5 minimum on card. So this gap is a different size depending on the day: nothing at all in January and February, and nothing Monday to Wednesday for the rest of the year.

Navigation: The most forgiving navigation on the trail. Acorn waymarking is consistent and the drove road is unmistakable; the route runs through the yard at High Paradise Farm rather than around it, which is the only bend that is not obvious from the ground.

The hardest walking on the trail. It opens with a zigzag flight of steps out of Scugdale onto Live Moor, then delivers the Cleveland escarpment as a run of separate tops, each with a full climb and a full descent and almost no level ground between them: Carlton Bank, Cringle Moor, Cold Moor, Hasty Bank. Long stretches are laid with stone flags, which makes the flatter ground fast and the wet slabs slick, and the steepest descents are gravel path and stone steps. The Wainstones on Hasty Bank are a short hands-on scramble through sandstone blocks, the only place on the trail where you put a hand down. After the steps to the Clay Bank road the character changes completely. Urra Moor is a broad paved trod over the highest ground in the North York Moors, and from Bloworth Crossing the trail joins the trackbed of the old Rosedale ironstone railway, level and near-straight for several kilometres round the moor edge, with the last drop into Kildale on tarmac.

Logistics: From the Clay Bank road at about 49 km there is no road contact and nowhere to stop until Kildale, roughly 14 km of open moor and trackbed.

Navigation: Waymarked and obvious along the escarpment, where the ridge does the navigating for you. Bloworth Crossing is the exception and the hardest point on the trail to get right: several tracks meet on featureless moor with no landmark, and the Coast to Coast and Lyke Wake Walk cross here too, so in cloud it is worth a compass bearing rather than a guess.

A short linking stretch with more variety than its length suggests. It starts on tarmac, a steady road climb out of Kildale through Mill Bank Wood before the moor opens at Captain Cook's Monument on Easby Moor. From there it is dry sandy heather trod across Great Ayton Moor with Roseberry Topping's quarried cone ahead. The official line crosses the shoulder below the summit and the top is a steep stepped out-and-back of about twenty minutes, which most walkers take. Beyond it the trail runs east along the moor edge to Highcliff Nab, a sandstone outcrop where the sea appears for the first time, then drops into Guisborough Woods and stays inside forestry for several kilometres, sheltered, enclosed and viewless, before emerging near Slapewath. There is nothing open anywhere between Kildale and the far end.

Logistics: Carry the day's food and water from the start. The next mapped shops and pubs are at Slapewath and Skelton at the end of the section.

Navigation: Two places to pay attention. On the moor past Roseberry Topping the tempting line follows a drystone wall, while the route takes the track across the moor, and this is where walkers report going wrong. In Guisborough Woods the forestry tracks cross repeatedly and the acorns need looking for rather than glancing at.

The hinge of the trail, and the only part of it that feels suburban. It begins in worked-out ironstone country around Slapewath and Charltons, crosses the main road and climbs out through plantation and field paths, then threads Skelton, where the line runs through a modern housing estate and reads more like a town walk than a national trail. From there it drops into the wooded gorge of Skelton Beck, passes under the railway viaduct and comes out through Valley Gardens onto Saltburn seafront beside the pier. That is the moment the Cleveland Way stops being a moorland walk and becomes a coast walk for the rest of its length. From Old Saltburn it climbs onto Hunt Cliff, the first sea cliff, swings round Warsett Hill above a working railway line, then drops to firm sand across Cattersty Sands and the stone jetty into Skinningrove.

Logistics: Saltburn at about 86 km is the best-stocked town on the trail between Helmsley and Whitby, with a station in the town centre.

Navigation: Well waymarked and busy with local walkers around Saltburn, and easy underfoot. The exception is Skelton, where the trail crosses a housing estate built and rebuilt around it and where walkers report losing the line entirely.

The long coastal section, and the one that defines the trail. It is clifftop grass and field-edge path almost throughout, broken by a run of steep drops to sea level and equally steep climbs back out at Staithes, Runswick Bay, Sandsend, Whitby, Robin Hood's Bay, Boggle Hole and Stoupe Beck. Boulby, early on, is the highest cliff on the English east coast and carries no marker at the top, and the path down its vegetated seaward slope is indistinct enough to make you check. The exception to the clifftop rhythm is Kettleness to Sandsend, where a stepped path with handrails drops off the cliff onto the trackbed of the old coastal railway and runs level and sheltered to the sea. Whitby is the pivot: streets, the swing bridge over the harbour, and the 199 steps up to the abbey headland. Beyond Robin Hood's Bay the two wooded ravines at Boggle Hole and Stoupe Beck give the steepest short climbs on the trail, and the final pull inland past the Peak Alum Works onto the Ravenscar plateau is a long steady 200 m gain at the end of a long day.

Logistics: The official route crosses the sands at Runswick Bay and rounds the rocky shelf at Hob Holes, a short stretch that is under water at high tide, so the day needs planning around it. Waiting an hour for the ebb is the usual answer. Heavy rain is a separate problem there: the gully is stream-fed and the stepped stones can be awash whatever the tide is doing. Robin Hood's Bay is where the signed line moves. The approach from the north has run inland since 2021, across Rocket Post Field and down a ramp onto a short stretch of the Cinder Track, and that is the route now rather than a diversion. South of the village the cliff path was closed in January 2026 for a rebuild of the steps, with walkers sent inland by Middlewood Farm, the Cinder Track and Mark Lane. The trail's own information page lists whichever diversions are running, and on this stretch it is worth reading the week before rather than trusting a stored track.

Navigation: Acorn waymarking on the cliff path itself is thorough and hard to misread. Whitby is the exception: the line through the town between the harbour and the abbey steps is poorly signed and needs a map. The other durable point is that these are soft clay cliffs which slip regularly, so signed inland diversions are a normal feature of this coast rather than an emergency, and it is worth walking the current signs rather than an old track log. There is a second reason the line moves here. Six scheduled alum working sites sit on this coast, Boulby, Kettleness, Sandsend and Saltwick Nab among them, and the National Park's position is that they cannot be defended: it expects them to be worn away over the next century and is recording them archaeologically instead of trying to save them. The same erosion that is taking the monuments takes the path above them, which is why temporary fencing and short inland re-routes appear on this stretch at little notice.

Easy-looking on paper and easy for most of its length, with one exception that walkers remember. From Ravenscar the trail runs south on high, open clifftop past a wartime radar station, a long way above the sea and with few features to break it. Then Hayburn Wyke: a long flight of steps down into a wooded ravine to a boulder beach, and an equally long climb out the far side, which most people rate the hardest part of the day despite the modest overall ascent. After Cloughton Wyke the cliffs lower and the going turns to easy grass and field edge past Crook Ness and Scalby Ness. At Scalby Mills the cliff path ends outright and the trail becomes urban seafront, promenade past North Bay and Peasholm and round beneath Scarborough Castle into the old harbour. The old Scarborough to Whitby railway, now the Cinder Track, runs roughly parallel a little inland and is commonly used as the return leg of circular walks from Ravenscar.

Logistics: The stretch between Ravenscar and Scalby Mills carries the longest gap between mapped shops on the coastal half, around 21 km.

Navigation: Waymarked and straightforward on the cliffs, with acorns at the changes of direction. The only place to think is the Scarborough seafront, where the route runs the promenade and round the castle headland rather than through the town, and the acorns compete with a great deal of other signage.

A short finish that is never actually flat. From the Spa the trail climbs steadily up landscaped ground on the site of the former Holbeck Hall Hotel onto Wheatcroft Cliff, then runs the clifftop south. At Osgodby the cliff path is closed off by housing and the route turns inland and uphill onto a residential road before dropping through undercliff woodland to Cayton Bay, which is the one real descent and climb of the day. Beyond it the cliffs are soft clay, low and actively eroding, and the path runs close to the edge in places, most obviously at Red Cliff. From Gristhorpe onwards the going is level cliff margin with Filey Brigg in sight ahead, and a single steep-sided gully to cross before the descent into town. The trail ends at the monument above the Brigg.

Navigation: Acorn-waymarked and hard to get wrong on the cliffs. The one counter-intuitive point is Osgodby, where the trail leaves the cliff and climbs onto a residential road before returning to the coast. It is signposted, but walkers whose instinct is to stay with the sea miss it.