How difficult is the 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.

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.

In poor weather: The escarpment from Sutton Bank to Boltby faces west and takes weather head on, and in low cloud it loses the view that is its entire point. Rain matters more for footing than for exposure here: the wooded steps around Rievaulx and the stones on the Oakdale descent are the slippery ground, while the drove road drains well and stays quick in the wet.

Escape options: Sutton Bank at about 12 km has a car park, visitor centre and a road, and Osmotherley at 31 km has buses and full village services. Between them the only road contact is the lane end at Sneck Yate and the crossing at Square Corner above Oakdale, both minor and remote.

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.

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.

In poor weather: The escarpment tops face north over Teesside and there is nothing to break a northerly; walkers report the wind on Cringle Moor as the thing that slowed them, and the lee of the Wainstones as the first shelter. The flagstones are noticeably slippery wet and the scramble is harder in rain. Beyond Clay Bank, Urra Moor and the trackbed give around 10 km with no shelter and no features to steer by in low cloud.

Escape options: The Carlton Bank road crossing at about 43 km and the Clay Bank road at about 49 km are the two realistic bail-outs, both with parking and a road down off the escarpment. After Clay Bank there is nothing until Kildale, which has a station on the Esk Valley line a few minutes from the trail.

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.

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.

In poor weather: Easby Moor, Great Ayton Moor and the Roseberry shoulder are fully open, and the sandy trods hold standing water in the peaty hollows after rain. Roseberry Topping's summit path is stepped and steep enough that wind is a fair reason to skip the detour. Guisborough Woods is the only real shelter between Clay Bank and the coast.

Escape options: Kildale station at the start. After that the one realistic exit is Gribdale Gate at about 68 km, where a lane drops roughly 1.5 km downhill to Great Ayton and its station. Guisborough town lies directly below Highcliff Nab but the drop off the Nab is steep and off-route, so the practical exit from the forestry is to carry on to Slapewath.

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.

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.

In poor weather: A day of two exposures. Everything as far as Saltburn is wooded, enclosed or built-up and largely sheltered; from Old Saltburn onwards there is nothing between the path and the North Sea, and the climb onto Hunt Cliff is where the wind arrives. Cattersty Sands is firm and stays walkable in rain, though the beach line depends on the sea state rather than on the path.

Escape options: The easiest exit on the whole trail. Saltburn has a station in the town centre and buses; Skelton and Brotton sit on bus routes just inland and are reached by short lanes. Skinningrove is at the bottom of a steep valley but has a road out.

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.

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.

In poor weather: Rain does more here than wind. The clifftop grass and the field paths behind it churn to mud quickly, and the steep steps in and out of each village and ravine become the slowest ground on the trail when wet. Hob Holes at Runswick is stream-fed and can be impassable after heavy rain whatever the tide is doing. Low cloud removes the views that are the point of the section but does not threaten the route-finding.

Escape options: The best-served stretch of the trail. Staithes, Runswick Bay, Sandsend, Whitby, Hawsker and Robin Hood's Bay all sit on or just off the coast road with bus services, and Whitby has a station in the town. Ravenscar at the far end is the awkward one, high above the sea at the end of a dead-end road, so it is a poor place to be stuck.

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.

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.

In poor weather: The run from Ravenscar to Hayburn Wyke is the most sustained piece of open clifftop on the coastal half, with nothing to shelter behind, and the moor and sea-cliff weather here changes fast enough that poor visibility in summer is normal rather than unusual. The Hayburn Wyke steps are wooded, steep and slick in the wet. The final promenade is at sea level and fully open to the east.

Escape options: Cloughton and Burniston are a short way inland on the Scarborough to Whitby road with bus services, reached by lanes from the cliff. Ravenscar at the start is on a dead-end road. Once past Scalby Mills you are inside Scarborough and can leave anywhere.

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.

In poor weather: These are soft clay cliffs, so wet weather makes the path itself slick rather than merely muddy, and it is the ground near the edge that gives way. Deep-lugged boots earn their keep here more than on the harder moorland surfaces earlier in the trail. There is no shelter along the cliff line, but nor is there anything here that closes the day.

Escape options: The easiest section to leave. The coast road and its year-round bus service run close and parallel for most of the way, with lanes up from Osgodby, Cayton and Gristhorpe. Filey has a station, though it is a walk of 20 minutes or so from the trail end at the Brigg.