From the mainland, the Isle of Portland looks daunting: a dead-straight, narrow causeway beside a stony stretch of beach leading to a dismal-looking port and a prison. But its hinterland is a lonely, ragged beauty: a dozen square kilometres of hilly coastal trails; ancient ruins, hidden coves, mysterious huts, the scars of disused quarries and a littering of military structures. For walkers like me, it is irresistible. Hardly anyone I know has ever visited.
Locals claim the island on Dorset’s Jurassic coast was one of the first places Vikings landed in Britain — at Church Ope, a cove full of stones beneath limestone cliffs. It is a miracle the longboats made it. Dozens of ship and submarine wrecks lurk beneath Portland’s waters — there’s a helpful map in the island’s museum — and its racing sea currents add to a sense of menace (one beach is known as Deadman’s Bay).
The wilderness ends at Portland Bill, a lighthouse that looms over a scattering of huts, a coast banked with rocks and an ominous stone slab known as Pulpit Rock. Thomas Hardy called the island “the Gibraltar of Wessex” — carved by the sea from a single mass. But Portland’s stone is also its fortune: it provided the material for many of London’s public buildings, churches and palaces.
It is also highly protected, part of a Unesco World Heritage site and with several Sites of Special Scientific Interest. In spring, thousands of migratory birds land here. All of which means few new buildings are approved.

When the owners of Pennsylvania Castle Estate, a neo gothic mansion and events venue overlooking the sea, wanted to build a terrace of holiday lodges on the edge of a nearby cliff, English Heritage’s approval was contingent on the specific instruction that the lodges resemble an 18th-century hermitage. The conservation body wanted the development to be craggy and unobtrusive, as if it had always existed as part of the cliff.
The London architectural firm Morrow + Lorraine has done a remarkable job with that brief, with the added complications of building on a sliver of land next to the Grade-I listed, 15th-century Rufus castle, and above the ruins of an ancient church.

Clifftops, which opened during the pandemic, is five single-storey, two-bedroom lodges of Portland stone and weathered copper, set into cliffs on the island’s eastern coast, 50 metres above sea level. The lodges fan out across the cliff so each is private, and are set so low as to be virtually invisible to passing boats, swimmers in Church Ope cove below, and walkers on the nearby trail. Unlocking my lodge, I am greeted with an immense, dramatic sea view framed by glass walls, with sun flashing across currents racing from Lulworth Cove, 20km away on the mainland. It is achingly pretty.
Clifftops’ stability is down to a feat of structural engineering. The lodges have been stitched to the land with 80 metal piles, sunk vertically and diagonally into its limestone layers, pinning them to the cliff.



When the lodge’s vast windows are closed, the wind falls silent. My bedroom, like all on this site, has a sea view. l do feel like a hermit, albeit one with a high-end mattress; an enormous outdoor cooking range, a clifftop hot-tub and Netflix.
These are luxurious places, with interior walls lined with polished Portland stone studded with the fossilised shapes of shells, fish and oysters. Frank Gilks, the chief architect, tells me they were hewn from younger rock than the rough, exterior stone “as if you’re walking into the ground, almost cave like and into something that has always been there”.
The interior is a little Scandi-bland, a sea of mid-century style grey soft-furnishings and blond wood. But it does have the advantage of not detracting from the drama outside.

According to its owners, Clifftops is aimed at walkers, rock climbers, sailing enthusiasts, people booking “workations” and wedding parties from Pennsylvania Castle — though I only intend to walk. Portland’s stretch of the South West Coast Path is an easy-to-traverse loop of roughly 15km. The path is teeming with wildflowers, grasses, early butterflies and nesting birds: I see peregrine falcons, guillemots and kittiwakes — and very few people.
From the path, I make an inland detour to St George’s church, built in 1766. Its elaborate exterior resembles Wren’s London churches; inside, its pulpit and box pews survive. Most evocative is its cemetery, with tombstones facing seaward in rows. One inscription tells a tale of violent murder; another of killings by a press gang. The Luftwaffe tried to bomb St George’s but missed, hitting part of the graveyard. The islanders filled the crater with the remnants of shattered memorials — it is still there.
I am starting to wonder how hermits hold out. After a day of solitary rambling through landscapes of desolate charm, I head back to the mainland for dinner at Catch, in the Old Fish Market on Weymouth harbour. The restaurant opened last year and is extremely busy — even on a Wednesday evening in April.



Catch is tricky to find, hidden from street view in the Victorian market’s recently refurbished loft, which also houses an open kitchen. It specialises in fish and seafood caught by the boats that deliver outside, and wines from the English south coast with, it says, menus that change with the seasons and tides. Once I am in, the chefs call their recommendations to me, suggesting turbot. A chubby fillet with sea purslane is brought with a glass of sharp crémant from the Bride Valley vineyard, about 10 miles inland. The fish is fabulously fresh.
Later, I call Gilks to ask him about that curiously specific hermit brief from English Heritage. He tells me the local planning officer turned up to an early meeting wearing a badge that read “Keep Portland Weird”.
Back at Clifftops and out on the terrace, it feels as if the wind might carry me away. I have an almost queasy — but not unpleasant — sense of being suspended in space and air. It is hard to believe that this row of dwellings will not tumble into the sea at any minute.
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Helen Barrett was a guest of Clifftops (thepennestate.co.uk). Each of the lodges sleeps up to four, in two bedrooms, and costs from £1,050 per week in low season and from £2,082 in high season. For more on visiting the area see visit-dorset.com
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