Cleveland, Guisborough 5 Sleeps, 1 Bedroom, (new)
Tucked away in northeastern England, Cleveland is a region that whispers tales of Vikings, explorers, and ironstone miners. The name Cleveland comes from the Old English 'clifa land,' meaning 'district of cliffs,' perfectly describing this dramatic landscape where the rugged Cleveland Hills meet the spectacular North Sea coastline. This is a place where the past weaves seamlessly into the present, offering glamping guests an experience far removed from the ordinary.
Cleveland stretches across what is now primarily Redcar and Cleveland and parts of North Yorkshire, positioned along the River Tees and bordering the North York Moors National Park. The region includes characterful towns like Middlesbrough, Saltburn-by-the-Sea, Guisborough, and Great Ayton, each with its own distinct personality. For visitors arriving from international destinations, Durham Tees Valley Airport and Newcastle Airport provide convenient access, while excellent rail links connect the area to major cities across Britain.
Cleveland offers glamping guests something increasingly rare: authentic British landscapes without the overwhelming crowds. The region sits at the gateway to the North York Moors National Park, one of the largest expanses of heather moorland in England and Wales, covering 554 square miles of protected countryside. This National Park was designated an International Dark Sky Reserve in 2020, meaning guests can witness up to 2,000 stars on a clear night, including the Milky Way in all its glory.
The Cleveland coastline forms part of the North Yorkshire and Cleveland Heritage Coast, featuring Boulby Cliff, the highest cliff on England's eastern seaboard at 203 metres. This stretch of coast combines sandy beaches, dramatic cliffs, and quaint fishing villages that have changed little over centuries. The climate is typically maritime, offering mild temperatures ideal for year-round outdoor exploration.
For glamping enthusiasts seeking walking adventures, Cleveland is unmatched. The region boasts nearly 1,400 miles of public rights of way within the National Park alone, with most moorland areas open for access under the Countryside and Rights of Way Act. Whether you prefer gentle coastal strolls or challenging moorland treks, this landscape accommodates every level of adventurer.
The Cleveland Way National Trail is one of England's original National Trails, stretching 109 miles from the market town of Helmsley to Filey on the coast. Officially opened on 24th May 1969, it was only the second National Trail recognised in England and Wales. The trail follows a horseshoe route around the North York Moors National Park, offering two distinct experiences: the inland heather moorland section and the dramatic coastal walk.
Up to 2,000 hikers complete the entire route annually, while another 350,000 visits are made to various sections for shorter adventures. The trail passes through landscapes rich with history and heritage, including ruined abbeys, ancient stone crosses, and fishing villages tucked into tiny coves. Late August through early September offers the magical sight of blooming heather painting the moors in shades of purple.
Rising to 320 metres, Roseberry Topping is perhaps Cleveland's most iconic landmark. Its distinctive half-cone shape with a jagged cliff has earned it the nickname 'Yorkshire's Matterhorn,' and it features prominently in the logo of nearby Teesside International Airport. The hill's striking silhouette can be spotted from distances of up to 20 miles away.
The history of Roseberry Topping reaches back to Viking times. The name derives from Old Norse, first recorded in 1119 as 'Othenesberg,' believed to mean 'Odin's rock,' making it one of only a handful of places in England named after a pagan Norse god. The dramatic shape we see today resulted partly from a landslip in 1912, caused by a combination of geological factors and ironstone mining beneath the hill.
Now managed by the National Trust and situated just within the North York Moors National Park, Roseberry Topping offers 360-degree panoramic views from its summit. On clear days, visitors can see the Cleveland Plain, the North York Moors, the industrial heritage at Teesmouth, and even the coastline. A spur of the Cleveland Way National Trail leads to the summit, making it accessible for walkers of varying abilities.
Cleveland holds a special connection to one of history's greatest explorers, Captain James Cook. Though born in Marton near Middlesbrough in 1728, Cook spent his formative years in the village of Great Ayton, arriving when he was eight years old and remaining until he was sixteen. The village lies at the foot of the Cleveland Hills beneath Easby Moor and Roseberry Topping, with the River Leven flowing through its two village centres, High Green and Low Green.
As a boy, Cook worked as a farm hand at Airey Holme Farm and regularly climbed Roseberry Topping to enjoy the spectacular views. These early exploits are said to have given him his appetite for adventure. A monument to Cook stands on Easby Moor, an obelisk erected in 1827 by Robert Campion, a wealthy Whitby banker. The monument offers sweeping vistas north to Roseberry Topping and over the Cleveland Hills.
The Captain Cook Schoolroom Museum occupies the building where Cook received his education. Meanwhile, a granite obelisk marks the original site of the Cook family cottage in Great Ayton, as the cottage itself was dismantled and shipped to Melbourne, Australia in 1934, where it was rebuilt stone by stone in Fitzroy Gardens.
Saltburn-by-the-Sea developed as a Victorian resort and retains much of its original character, including the only remaining pier in the whole of North East England and Yorkshire. The pier, completed in 1869, extends into the North Sea and has witnessed 150 years of seaside history.
The Saltburn Cliff Lift is the oldest operating water-balance cliff funicular in the United Kingdom, opened in 1884 and still functioning exactly as designed by its Victorian engineers. This remarkable piece of engineering connects the upper town with the seafront, featuring a 71 per cent incline and a height of 120 feet. Two 12-person cars with stained glass windows travel along parallel tracks, powered by water filling and emptying from tanks, creating a unique experience that transports visitors back to an earlier era.
Beyond its Victorian heritage, Saltburn has gained modern recognition as a popular surfing destination. The town's fine sandy beaches and consistent waves attract surfers year-round, while its valley gardens and woodland provide peaceful retreats for those seeking quieter pursuits.
Founded in 1119 by Robert de Brus, an ancestor of Robert the Bruce, King of Scotland, Gisborough Priory was one of the first Augustinian priories built in England. The ruins are dominated by the dramatic skeleton of the 14th-century church's east end, standing 71 feet tall and representing an outstanding example of early Northern Gothic architecture. By the time of its dissolution by Henry VIII in 1540, the priory had become the fourth wealthiest monastic house in Yorkshire.
Tucked between two bulky headlands near the highest cliffs in England, Staithes retains much of the authentic character of a traditional fishing community. The village features a labyrinth of narrow cobbled lanes, including Dog Loup, claimed at just 18 inches wide to be the narrowest alley in England. This is where young James Cook first worked as an apprentice grocer before finding his calling at sea.
At the turn of the 20th century, 80 full-time fishing boats operated from Staithes. Today, traditional coble boats still set out from the harbour, maintaining centuries-old seafaring traditions. The village also nurtured a famous group of impressionist painters in the early 1900s, with Dame Laura Knight being the most celebrated member of the Staithes Group.
During Victorian and Edwardian times, Cleveland was the most important area of ironstone mining in England, fuelling the industrial revolution that transformed Britain. The Cleveland Ironstone Museum offers visitors the chance to experience the underground environment of these historic miners, preserving an important but often overlooked chapter of English history.
Cleveland enjoys good transport connections despite its feeling of remoteness. The Esk Valley Line railway runs between Middlesbrough and Whitby, stopping at villages including Great Ayton. This scenic route provides an excellent car-free way to access walking routes and attractions. Bus services connect major towns, with the Moorsbus service running on weekends during summer to more remote parts of the National Park.
For those driving, the A19 provides the main north-south route through the region, while the A174 follows the coast. Parking is available at most attractions and villages, though popular spots like Roseberry Topping can become busy on fine weekends.
The best times to visit depend on your interests. Late August and early September bring the spectacular heather bloom across the moorland. Spring offers bluebell displays in Newton Wood near Roseberry Topping. Winter provides dramatic coastal scenery and excellent stargazing conditions, while autumn's changing colours transform the wooded valleys.
Cleveland rewards those who take the time to explore beyond the obvious attractions. This is a region where Viking history meets Victorian innovation, where world-famous explorers took their first steps toward adventure, and where the raw beauty of moorland and coast remains largely unspoiled. Book a glamping stay and discover why this corner of England has inspired artists, adventurers, and wanderers for centuries.