Win Green

From the peak of Cranborne Chase in the heart of an ancient landscape, scattered with pockets of woodland and split by winding lanes, soak up the views across the south of England. Wander down into the wooded valley of Ashcombe Bottom where a Georgian Manor House sits. The estate’s tranquil beauty won the hearts of both artists and celebrities. Residents over the years have included Cecil Beaton and Madonna, entertaining guests such as Salvador Dali and Brad Pitt. Follow the old tracks to the Royal village of Tollard, the Manor House once fit for a king who hunted the wild Chase. Climb back out the valley, skimming Rushmore estate, the home of the Larmer Tree, to join ancient droveways. Encounter hillforts and prehistoric earthworks sat on ridges, surrounded by legends and looking out to Salisbury Cathedral and Glastonbury Tor. Pass the extravagant gardens of Viscount Rothermere’s Ferne House to then return to Win Green marked by a clump of Beech trees, hiding their own spiritual treasure.

Distance: 5.5 miles/9km (see map at bottom of page)

Duration: 2-3 hours

Ability: Easy, some steep slopes.

Max Height: 909ft.

Min Height: 350ft.

Total climb: 600ft.

Terrain: Track, path, road and field.

Map: OS Explorer 118 Shaftesbury and Cranborne Chase.

Start Point: Win Green Car Park. (Postcode: SP7 0ES, Grid Reference: ST923204, What Three Words: bakers.alienated.polished).

How to get there: From Shaftesbury, travel East on the Salisbury Road (A30) to Ludwell and turn right onto Dennis Lane. Cross straight over the crossroads, following the sign to Rushmore and onto Donhead Hollow. Continue to the top of the hill to then make a sharp right onto a chalk track. Follow the bumpy route for 100 metres to find the public car park.

Dogs: In accordance with the Countryside Code and any notices on route.

Refreshments: Just off route is The King John Inn in Tollard Royal and nearby is The Museum in Farnham

Win Green is a hill top in South West Wiltshire and is the highest point on Cranborne Chase at 277 metres (909ft) high. The peak provides visitors with panoramic views to Bournemouth and the Isle of Wight in the south, around to the spire of Salisbury Cathedral in the East and Glastonbury Tor, and the Quantocks in the North and West. From the surrounding valleys the hill is easily recognised by its clump of beech trees sitting on its summit.

Win Green would have had a perfect view point over the medieval hunting ground of Cranborne Chase, which today has been designated as an Area of Outstanding Natural Beauty as well as a Dark Sky Reserve. Having been kept wild for centuries, under the management of William the Conqueror and King John, the landscape is sparsely populated. The countryside became a perfect haven for poachers and smugglers during the 18th century meaning it was susceptible for the odd skirmish and even murder. The hunting rights were abolished in 1828 leading to the destruction of swathes of forest that once covered the landscape. Today it is a scene filled with small country lanes and pockets of woodland, peppered with earthworks of ancient sites.

Win Green and it’s clump of Beech trees

Facing the trees of Win Green, take the right hand footpath that leads away from the peak and the carpark. Keep to the Wessex Ridgeway, heading gently down the hill. In the distance to the left is the hillfort of Winkelbury while sitting below the ramparts is the fading scar in the landscape of the ancient Ox Drove. Climb the stile and continue down the hill, ignoring the gate on the right hand side. Slowly the sunken valley of Ashcombe Bottom reveals itself, disappearing to the south as it snakes its way between the steep spurs. Head through the heavy metal gate and continue down the hill into the private estate of Ashcombe. On meeting a track at the bottom, turn right to continue on the footpath. The paths through the estate do not quite match up with the data from either the OS or Google, nevertheless, the odd signs and marked terrain help to navigate the landscape. Head down the slopes to exit the trees into a small dry valley sitting on the edge of Under Win Green. Cross straight over and turn left to join another track. Depending on the season, glimpses of Ashcombe House slowly appear amongst the trees at the top of the hill on the left. Follow the track to then merge with a gravel road.

Entering Ashcombe Estate


Ashcombe House, set in Ashcombe Park, covers a total of 1,134 acres (459 ha). In the heart of the estate sits the Georgian Manor House. The first house recorded in this location was built in 1686 by a local squire called Robert Barber. In 1740, the Barber family entirely demolished the original house and rebuilt on the site to a much grander scale, including an orangery (the stables) and gatehouse. Ten years later the house was inherited by Anne Wyndham who, the following year, had married the Hon. James Everard Arundell, third son of the 6th Baron Arundell of Wardour. Together they then remodelled the interior.

The Ashcombe House of the Arundells c.1770 (Image: Salisbury Museum)

In 1815 the Ashcombe Estate was sold to Thomas Grove the younger who lived at nearby Ferne House. His Grandson, Walter, demolished the 1740 house and built the majority of what still stands today, although some has also been lost. The house passed through the hands of the 13th Duke of Hamilton before being purchased, in a slightly dishevelled state, by Mr R.W. Borely after World War I.

Ashcombe House today

In 1930, Ashcombe had its first famous resident, the photographer and designer, Cecil Beaton. Beaton fell in love at first sight with the manor and subsequently leased Ashcombe from Mr Borely for a mere £50 a year, on the condition that he would make improvements. Beaton fulfilled his promise and more, installing electricity and water as well as converting outbuildings back into habitable cottages and the orangery into his own studio. He hosted many lavish parties with guests including Salvador Dali, who even sketched his own Ashcombe House. Beaton’s lease expired in 1945 and he was heartbroken to leave.

Nancy, Cecil and Baba Beaton at the entrance arch of Ashcombe House c.1930 (Image: BBC)
Salvador Dali’s ‘Ashcombe’

Borely’s son, Hugh, moved into the property that same year. He was a slightly eccentric character who spurned the fame that Beaton had brought to the house. He was private too, receiving only a few visitors and chasing away any passing walkers, occasionally threatening them with guns! In his solitude he turned to whisky and in turn showed little respect to the house. However, he was continuingly finding himself batting away offers from American millionaires to buy his estate. Hugh died in 1993 and the house was sold, the owners carrying out a number of renovations.

Ashcombe House from above (Image: Daily Mail)
The track to Ashcombe

In 2002 the house gained notoriety once again when it was bought by the singer, Madonna, and her husband the film director, Guy Ritchie. They divorced in 2009 with the estate transferred to Ritchie as part of the settlement. Ritchie has continued with improvements on the house and its out buildings, occasionally getting into trouble with the planning department, but all of which has been quickly rectified. He has also re-established wildlife including fallow deer, while developing the landscape into one of the top game bird shooting venues in the country. Out of his own interest he has also set up the Gritchie Brewery producing beer as well as gin, manufactured in his own farm buildings. In the summer of 2022, he expanded his businesses further with the purchase of Compton Abbas Airfield to the west. Just like Beaton he has been the host to many a lavish party with guests including celebrity royalty such as Brad Pitt and David Beckham.

Brad Pitt with the Orangery and entrance arch behind (Image: Daily Mail)

On meeting the gravelled road, one of the main tracks through the estate, turn right. After only a few meters, veer off to the right cutting the corner by climbing the spur. Ashcombe House can again be seen, towering from above, its face looking down its own sheltered valley.

Skim the left hand side of the trees over the spur and then back down to the road. Continue following the road away from Ashcombe to pass Batercombe House. Walk over the cattle grid and when the road bends to the right, continue straight ahead onto the grass. In about 50 metres or so, head through the gap in the fence on the left hand side (no sign to mark the way) to a quarry and turn right, entering into hazel coppice and curving with the field. On meeting a fenced boundary turn right to head down the hill to another heavy metal gate on the left. Head through the second wooden gate and then bear left rising up to a third gate to meet a track. Follow the track, with the boundary on the right, all the way down the valley to Tollard Royal.

Batercombe House
Walking along Ashcombe Bottom

The village of Tollard Royal sits on the border between Dorset and Wiltshire. The Royal was attached to the name in the 16th century due to the claims that King John had a hunting seat here, although there are arguments that he spent more time in Cranborne than Tollard. The village and estate, including Rushmore Park, were sold to George Pitt in 1819, eventually inherited in 1882 by the famous archaeologist Augustus Lane-Fox, who adopted the name Pitt Rivers. The land is still with the same family today.

Tollard Royal Pond

Pass old barns, farmhouses and thatched cottages to arrive at the pond, which used to be the focal point of village life. Cross straight over the B3081 at the junction, with the grumpy faced Old Cart Shed on the right. Once over the B3081 skim past the war memorial and the old Blacksmiths cottage on the right, following the narrow lane to the church.

The indifferent Old Cart Shed
The old Blacksmith’s
1884 OS Map of Tollard Royal showing The Queens Arms, St Peters Church, King Johns House, the pond and the old school.

Records of a church being in this location date back to the 13th century. The doorway, tower arch and a selection of windows all still survive from this period. Little other alterations have occurred other than enlargement in the 16th century and a new roof in the 1850’s. It was dedicated to St Peter in Chains in 1469 and is an unusual title, although also adopted by Lytchett Matravers’ pub St Peters Finger in Dorset.

The church of St Peter’s

Inside there are colourful inscriptions on the wall and many memorials to the Pitt Rivers family. Augustus has his own little sarcophagus as a memorial; he was actually one of the first few bodies to be legally cremated at the time, which was his request. The tomb is decorated with surveying equipment and bones, something to honour what he himself had discovered many times before. The Gronow Davis family is also commemorated in both the church and graveyard, having acquired the estate in 1999, William Gronow-Davis being the last partner of Michael Pitt Rivers. In the heart of the church is a large effigy of Sir William Payne. He died in 1388 and is depicted as a crusader, but it is unlikely that he was. However, he was a knight and gained the ownership of Tollard through his wife Eleanor.

Augustus Pitt Rivers’ memorial
The effigy of Sir William Payne (d.1388)

Behind the church sits the elegant, red brick and timber framed King John House. It began its life as a hunting box used by the King before his death in 1216. It was then developed into a hall house in 1240.  The building grew into a manor house for the Tollard Govis and Tollard Lucy families, adding wings, chimneys and stair turrets.  The house became unloved and dropped to the lower levels of society and became a mere farmhouse until Augustus inherited it in 1880. He proceeded to renovate the building, being sensitive to its own history. In 1890 he opened it to the public as a museum as well as a reading room for local villagers. After his death, the house was sold and by 1907 it had become a private residence. Today it is in the ownership of the Rushmore estate and has been split into a holiday lets or used as a wedding venue. The gardens look up the slopes towards the Lamer Tree Gardens where the Gronow Davis Tower can be seen.

King John’s House from the graveyard

Leave the church by the small arched gateway at the top of the churchyard and cross straight over the road onto the footpath. Head down the hill to return to the road. Turning left takes you to the King John Pub. The pub opened in 1885 and was originally called the Queen’s Arms but was changed by the end of the century to The King John.

The King John Inn

Turn right to return to the pond and then left retracing a few of your own footsteps. When the path splits take the right hand option, bordering Rushmore Park and climbing up the hill. In 1817, George Pitt rebuilt Rushmore House, now known as Sandroyd School. Once Augustus gained control he transformed the surrounding landscape by planting extensive tree avenues such as Bridmore Ride, today long overgrown but still visible and almost puts Badbury Rings to shame. He also created a deer park and menageries for a collection of exotic animals which included kangaroos, llamas, yak, reindeer and zebras. He also installed a golf course and a racecourse.

Boundary of Rushmore Park

Keep to the track following it through the trees and up the hill. The climb provides views to the left, over the valley of the path already undertaken. Pass a reservoir and soon Rushmore Park opens out to the east with the views gradually expanding over Cranborne Chase. Continue climbing and after the rows of Beech trees the clump of Win Green appears in the distance in the left. On the right lie the earthworks of Berwick Down.

The rows of beech trees on the edge of Rushmore estate

Berwick Down is a set of three main areas of earthworks. The earliest are the number of cross dikes, which cut off this small spur, along with number of Bronze Age barrows. There is also an Iron Age farmstead, which was abandoned but replaced with a Romano British settlement and then used for a number of subsequent centuries. Other than these periods of occupation the site remains a secret.

The earthworks of Berwick Down
Lidar of the Iron Age Farmstead
Cross Dikes

Walk past the bumpy ground and along the ridge between the two steep valleys either side. Cut through the raised earthworks of the Cross Dikes and onwards uphill. Curve around to the left to reach Monk’s Down sitting at the top of the valley. Skim between the road and the modest entrance to Ashcombe House to stay on the track, which becomes the Ox Drove.  

Passing through the cross dykes

Ox Drove, also known as Cranborne Droves Way, is one of the longest and most ancient routes in the country. It links Axminster in Devon to Ivinghoe Beacon in Buckinghamshire and today creates part of the Wessex Ridgeway. It has been suggested that the route was used to transport Portland Stone from South Dorset to Salisbury for the construction of the cathedral. During the medieval period it was mainly used to take livestock to market in Salisbury. Today it is a popular route for mountain bikes.

The modest entrance to Ashcombe House, alongside the ancient Ox Drove, at Monk’s Down

As you continue along the Ox Drove the Hillfort of Winkelbury appears on the slopes behind, jutting out to the north. It was excavated by Augustus Pitt Rivers in 1881 and led to the discovery of a number of Romano-British artefacts. Local legend claims there is a golden table hidden somewhere on the site, possibly taken from a nearby church away from the prying hands of the Crown during the reformation. Also on the site is a dead thorn tree. The plant is said to have magic powers and catches witches as they fly past at night, protecting the villagers below. At one time it was cut down, but all animals and women stopped producing children. On replanting, every cow had a calf, ducks and chickens laid eggs and every female became pregnant within six months. The story can vary claiming that the plant was a dead yew and it was Pitt Rivers who had it removed. Nevertheless, many remain adamant that the tale is true. The devil also has associations with the hillfort. It is claimed that if you march around the hillfort’s ramparts seven times, cursing all the way, the devil will appear on a large black horse and offer you one wish, but, try and trick you into losing your soul.

Looking back to Winklebury Hillfort
Aerial view of Winkelbury Hill (courtesy of Historic England)

Once past the little hump and hidden beacon, down in the valley on the right are the beautifully manicured landscaped gardens of Ferne Park. The first house was built here in 1225 by Phillip De Ferne. It passes through a number of different families over the centuries until 1809 when the house was demolished. Two years later a new house was built by Thomas Grove and stayed within the family for a century. In 1914 it was bought by Alfred Douglas-Hamilton, 13th Duke of Hamilton, who also bought Ashcombe. During the war his wife, Nina, turned the house into an animal sanctuary for the wealthy families of London to evacuate their pets to safety. When she died she outlined in detail in her will her desire that the house remain as a sanctuary, however the conditions were so strict they made the house unsaleable, eventually leading to the building being demolished in 1965 (with exception of the 18th-century gateposts). In 1991 the estate was put up for auction and was sold at £1,040,000 to Francis Dineley. He then flipped the property selling it to the Rothermere family, who own The Daily Mail.

Ferne House and landscaped gardens

Since the 90’s the family have made huge developments. The house was the first thing to be constructed, designed by John Quinlan Terry in 2001, who attended nearby Bryanston School. It cost a reported £40m, the design highly influenced by Came House near Dorchester and Terry was awarded with the Best Modern Classical House in 2003. In 2013 the building was enlarged adding two cuboid wings. The family have also developed the landscape, the tree avenues and managed pockets of woodland clearly seen from the tops of the hills.

Ferne House (Image: Q&F Terry, Architects)
Came House, Dorchester

Keep following the track to return to the beech clump at Win Green. Veer slightly left off the main track to aim straight for the trees. Within the centre is a Bronze Age Bowl Barrow, a site that has never been excavated, even by Pitt-Rivers, and so remains in a good condition. Therefore the barrow is still hiding its secrets from the world despite being visible for miles around.

Win Green
Lidar of Win Green’s Bowl Barrow

Continue straight ahead, passing the trig point, to return to the car park and your vehicle.

Win Green’s Trig point
Walk Excerpts

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