Despite its name, only a traveller coming from Poole will need a ferry to reach Dorset’s Isle of Purbeck, an island that’s not really an island, famous for its chalky downland, cliffs and quarries. Tucked into Purbeck’s hills, the village of Chaldon Herring, known also as East Chaldon, feels remote and sequestered. It’s the perfect place for a varied walk, with few roads, quiet valleys, a spectacular coastline and some intriguing history.

I made my way from the village green between thatched cottages past the church, where rooks noisily established their order of things. Leaving the village, I walked down a lane between rolling fields – plastic sheeting had been laid to warm the soil for crops, so the view resembled the swell of the sea, the foraging rooks imitating gulls. Under the long-nosed hill of High Chaldon at the end of the lane was West Chaldon, only a few houses and a farm, but once part of a larger settlement, Holworth, abandoned in the 15th century. The ebb and flow of human life over millennia is written into the ground in Purbeck. Just north of Chaldon is a barrow grouping known as the Five Marys. When excavated in the 1860s by an exiled Bourbon princess, the Duchess of Berry, the remains of two adults were discovered, one male, one female, both in sitting positions, stag antlers resting on their shoulders.

From West Chaldon I climbed through grassy fields, relying on a single isolated fingerpost to mark my route, a crooked and diminutive Angel of the South. Joining the South West Coast Path, I found Saint Catherine-by-the-Sea, a tiny wooden church in a patch of woodland above Ringstead Bay, serving a small, scattered parish and offering a few minutes’ rest and contemplation for walkers.

I had not chosen my day perfectly. As I reached the more exposed ground on the coast path, the rain began, at first pleasantly cooling, and then a squally barrage. The undercliff here is known as Burning Cliff – for several years in the 1820s the oil shale below ground burned and smouldered, a sign of Purbeck’s active, valuable geology.

I paused at White Nothe cottages on the headland – built as coastguards’ houses, they were once lived in by the writer Llewelyn Powys and his wife, the American novelist and feminist Alyse Gregory. Powys would be seen wandering the downs, dressed in a cloak, possibly on the way to visit his mistress, Gamel Woolsey. Chaldon Herring attracted a group of writers and artists – Llewellyn’s brothers, John Cowper and Theodore, both lived in the village, and Theodore fictionalised it as Folly Down in his 1927 novel Mr Weston’s Good Wine.

Two of the Powys sisters, Philippa and Gertrude, a novelist and artist respectively, also moved there. Adding spice to this already heady mix, Sylvia Townsend Warner and her partner, the poet Valentine Ackland, came to live in Chaldon Herring. Drawn to communism by the horrors of the Spanish civil war, the two women attracted the attention of MI5. Ackland and Townsend Warner were energetic presences in the village, organising dancing on the Five Marys as a republican alternative to George V’s Jubilee celebrations in 1935.

In front of the cottages was a squat brick pillbox, hunkered against the elements. Purbeck bears the marks of its military-industrial legacy – the ruined village of Tyneham, which was commandeered by the army for exercises in 1943, the quarries, the Winfrith nuclear reactors and Bovington Camp, close to where TE Lawrence lived in seclusion at Clouds Hill. Behind the pillbox I met two people sheltering from the near-horizontal rain.

In a grassy bowl further along the clifftop was a tall stone obelisk – from the sea, when aligned with its further inland twin, it was once a navigational aid for shipping. Standing in its relative shelter I ate my cheese roll. The rain eased, revealing a curving ribbon of hills and shining white cliffs to the east. The coast path here is sometimes steep and uneven: short distances on the map were long on foot. I was ready for a bracing walk, partly to dry off, but an easier path nearby would still offer wonderful seascapes.

A small slab shaped disconcertingly like a headstone invited me to take the Smugglers’ Path to the undercliff, also warning that it was a “steep hazardous route”. In the 18th and early 19th centuries, smugglers were busy along Dorset’s coast, using heathland tracks to take their goods to market. The county’s most famous practitioner was Isaac Gulliver, who kept poached deer carcasses in a fake tomb in the graveyard at Sixpenny Handley. His legend lives on: Wimborne’s bookshop is named after him, rather than Jonathan Swift’s hero. I avoided the criminal path and kept going to Bat’s Head, within sight of the massive rock arch of Durdle Door.

In the nearby well-kept holiday park I found a children’s play area featuring a wooden model of Lulworth Castle, roofless like the original which burnt down in 1929, now partially restored. The castle’s owners have long been keen to keep commoners at arms’ length, going so far as to relocate the village of East Lulworth in the 18th century, the settlement being a little too close to their ancestral home. The caravan park, owned by the estate, is also safely out of its view, but well placed for holidaymakers.

Heading inland, the path led me into open fields alive with lark song, and a silent wide valley perfect for transporting contraband. Ready for lunch, I reached the lane that took me back to Chaldon Herring, the Five Marys above me.

Google map of the route

Start/Finish The Sailor’s Return at Chaldon Herring
Distance 9 miles
Time 4 hours
Total ascent 549 metres
Difficulty moderate to difficult

The pub

Close to the village green, the Sailor’s Return, dating from the 18th century and once two cottages, is a long, low thatched building. The friendly pub is run by Tom and Amelia Brachi, who have owned it for eight years, and given it a fresh, simple interior, whitewashed walls complementing its flagstones.

The customers are a mix of locals and holidaymakers who return regularly, as do the Friends of Llewelyn Powys. The menu runs from small plates, like pulled-pork blinis and salt-baked beetroot paté, to substantial pies and vegetarian curries. I sat in the garden and enjoyed a lively pint of Cerne Abbas ale, and my plate of wild halibut on samphire was a tasty, salty slice of the sea.

Where to stay

The Sailor’s Return doesn’t have guest accommodation, but in the nearby village of Winfrith Newburgh is the pet-friendly Marley House B&B, which has six spacious double rooms named after trees and flowers, and a one-bedroom apartment.

Doubles from £140, marleyhouse.co.uk

Jon Woolcott works for the independent publisher Little Toller Books. He is writing Real Dorset, to be published by Seren