By Emma Chesworth

 

The charming market town of Helmsley has an ice cream shop that handily sits a stone’s throw from the Cleveland Way National Trail marker confirming that Filey is 175km/109 miles away. Mint choc chip cone in hand, I stroll out of town, and within minutes I reach the first of the historic buildings that make this route such a draw. Medieval Helmsley Castle is followed just 5km/3 miles later by the majestic monastic ruins of Rievaulx Abbey.  

 

Cleveland Way stages 1-4: crossing the North York Moors 

The Cleveland Way is traditionally broken up into a nine-day hike. About 90% of walkers begin, like me, at Helmsley, hoping for a helpful westerly wind on their backs.  

Heading west to begin with, I enjoy the dappled shade of the woods and coolness of the ponds in Nettle Dale. Crossing a stream, I spot wild orchids and a couple of walkers enjoying a nap on the grass, the sound of running water a natural lullaby. Nearing the North York Moors National Park, I stop to admire the gigantic figure of the Kilburn White Horse, dug out by a local schoolmaster in 1857 and given its white hue thanks to dozens of volunteers who deposited tonnes of lime into the sculpted ground.  

My finishing point for day one is Sutton Bank, the high point of the Hambleton Hills, with a vista over the Vales of York and Mowbray described by James Herriot (of All Creatures Great and Small fame) as ‘the finest view in England’. I enjoy coffee and cake at Sutton Bank National Park Centre and reflect on the day. The landscape’s palette of lush greens have been a feast for the eyes, the undemanding terrain a gentle introduction for the feet.  

The Cleveland Way attracted many nominations in the Ramblers’ Britain’s Favourite Path competition last year. Malcolm Hodgson, the way’s national trails officer, tells me why he thinks it’s so popular. ‘Chatting to people walking the route, it’s 100% the mix of coast and moorland that appeals, and what makes it particularly special. You get very different experiences throughout your nine days.’  

Malcolm estimates that between 1,000 and 1,500 people walk the full trail each year. ‘Doing the whole route day after day can be fairly life-changing for people,’ he says. ‘However, that doesn’t take anything away from being on it just for a few hours – there is magic even in the short walks.’  

Day two beckons and I make my way along the Hambleton Drove Road, contemplating the sheer expanse and wild beauty. This section was walked by Scottish cattlemen driving their herds down to market during the 18th and 19th centuries, and it feels as if little has changed.  

My finishing point, the pretty North York Moors village of Osmotherley, is dotted with a pleasing selection of cafés and pubs. As I sit outside enjoying a refreshing drink, I wonder how many of the walkers I see are also tackling the full trail.  

Bill Dell, a member of Cleveland Ramblers for 20 years, walked the Cleveland Way solo, his wife picking him up at the end of each day. ‘It was wonderful to complete the walk, as you pass so many interesting places,’ he says. ‘My favourite part has to be around Square Corner [near Thimbleby], as you get such an expanse of scenery.’  

Cleveland Ramblers was the driving force behind the Cleveland Way being designated a National Trail. Its inception was in the 1930s, when the then Teesside Ramblers called for a long-distance path. In 1953, a formal application to create the route was submitted, and it officially opened on 24 May 1969, becoming only the second National Trail in England and Wales.  

The 17.5km/11-mile stretch from Osmotherley to Clay Bank reveals the Cleveland Hills in all their raw beauty. Even on a sunny day, with many day-trippers out for a ramble, it’s possible to feel as if you’re the only person on Earth, such is the expanse as you cross five moors. But there are frequent reminders of the region’s busy industrial past, with evidence of alum, jet and ironstone mining in the abandoned quarries, mines and kilns.  

The highest point on the North York Moors is Urra Moor at 454m/1,490ft, then it’s downhill to the village of Kildale, passing moorland stone markers carved into features – I make out a face and a hand. Bloworth Crossing, once a railway crossing on the mineral railway line that served the ironstone mines of Rosedale, is the most remote point along the whole trail. I embrace being alone in the wilds before the next stretch to the bustling town of Saltburn-by-the-Sea.  

 

Cleveland Way stages 5-7: through Saltburn and Whitby 

The 22.5km/14-mile section to Saltburn is Captain Cook territory – the explorer is the most famous son of the village of Great Ayton. You can’t miss Captain Cook’s Monument, the obelisk erected in his honour, close to the mini Matterhorn of Roseberry Topping.  

With the sun beating down, the canopy of Guisborough Woods offers a reprieve from the rays. Further along, I walk through Saltburn Woods, and soon after I’m rewarded with my first glimpse of the sea. It’s a sight that will become more than familiar over the coming days, the blue waters a constant friend on my left for the rest of the walk.  

Saltburn is a popular seaside resort, home to the country’s oldest waterbalanced funicular railway still in operation and a Victorian pier. Many a time I’ve sat on the pier with a bag of chips, watching the swimmers, surfers and saunterers. The Saltburn to Sandsend stretch, at 28km/17½ miles, is the longest day’s walk on the route. The ascent to the clifftop offers stunning views – and not only of the coast. Look out for a series of art features, including the much-photographed ‘Charm Bracelet’ – a circular sculpture with 10 metal objects swaying in the breeze. The delightful fishing village of Staithes awaits. Depending on the tides, a reviving paddle at Runswick Bay is a tonic for aching feet before ascending the cliffs en route to Sandsend  

After Sandsend, it isn’t long until Whitby comes into view, and Dracula comes into my mind. The seaside town features in Bram Stoker’s classic novel. His vampire comes ashore at the headland here, and I reenact his climb of the 199 steps up to St Mary’s Church. Catching my breath, I take in the vista that includes the evocative ruins of Whitby Abbey.  

 

Cleveland Way stages 8 & 9: Robin Hood’s Bay to Scarborough 

Next stop is Robin Hood’s Bay. An infamous smuggling village in the past, nowadays it’s a magnet for day-trippers, with its quaint shops, quirky cottages and traditional pubs. Just north of the bay, work has been carried out to both improve the path and encourage nature recovery. Fences have been set back by about 10m/33ft, making a wider footpath on this busy part of the route. The works have also created a natural corridor to protect wildlife species and habits – a win-win for walkers and Mother Nature.  

On my penultimate day I’m headed towards Scarborough. Malcolm has a soft spot for this stage of the trail. ‘I really like the stretch south of Ravenscar, heading towards Cloughton and Hayburn Wyke,’ he tells me. ‘It’s a little bit quieter, and it has very dramatic cliff scenery.’  

This section has some steep declines, particularly the drop down into the cove of Boggle Hole (boggle meaning hobgoblin). On the approach to Ravenscar, the area’s industrial past is again evident as the route passes through the site of the former alum works, which produced dye fixatives vital to the 16th-century textile industry. The ruins of Scarborough Castle, on a rocky promontory, come into view at the end of the day’s walk. Beyond it, the town’s imposing Grand Hotel – the largest in Europe when it opened in 1867 – overlooks the sweeping sands of South Bay.  

One final day and the Cleveland Way is complete. The weather and light mean the coastal scenery is forever changing on the way to Filey. This section includes the former site of the Holbeck Hall Hotel, which, under the glare of the media, slipped into the sea in 1993. Coastal erosion is still evident, with original parts of the route now barred due to unstable rocks and the path moved further inland.  

As I approach Cayton Bay, an adjacent golf course is doing a roaring trade, and I pass the time with some golfers hunting for a ball in the rough. Nearby Filey Brigg peninsula attracts birdwatchers from far and wide, its steep cliffs sheltering puffins and purple sandpipers.  

The weather is cooling as I approach the sign that tells me I’ve made it to the elegant seaside town of Filey, the end of this trail. Another tells me the Yorkshire Wolds Way has an ending there, too. Perhaps this route south to the Humber Estuary will be my next adventure? 
 

Cleveland Way National Trail: distance, stages and map 

Distance

175km/109 miles from Helmsley to Filey. ACCOMMODATION There are plenty of places to stay along the route, particularly along the coastal section. Check out the official guides for accommodation and campsites and hostels.

Several companies run group or self-guided walking holidays along the trail, including Ramble Worldwide, which offers a 10-night, half-board guided holiday starting at £1,799. 

 

Accessibility

Some sections are suitable for wheelchairs and buggies, including around Sutton Bank near the start. Browse this National Trail guide for accessible and easy walks from the Cleveland Way.   

 

Getting there

The start point at Helmsley can be reached by bus from York or Scarborough.  
Filey, at the end, has rail services to Scarborough, Hull, Doncaster and Sheffield.  
There are plentiful public transport options along the coastal half of the route.  

 

Maps

OS Explorer OL26, OL27 and 301; OS Landranger 93, 94, 99, 100 and 101.  

 

Further Info

nationaltrail.co.uk/cleveland-way 
northyorkmoors.org.uk  

The Cleveland Way and the Yorkshire Wolds Way by Paddy Dillon (£17.95, Cicerone, ISBN 978 1786312212).