From a new castle to a ruined one, a hidden village to a demolished church. Over railway and through woodland, circling the old castles of Sherborne. The landscape loved by Sir Walter Raleigh, who even made himself a stone seat to sit, smoke, watch the deer run wild and the world go by! Discover the Keepers Cottage and the medieval road to London, where Sherborne Castle gateposts still stand to welcome the long gone horse drawn traffic.
Distance: 6 miles/8km
Time: 2-3 hours
Total climb: 520ft
Max height: 475 ft
Min height: 180 ft
Terrain: Track, path, field and road.
Exertion: Easy. Can be muddy and slippy, regardless of the weather.
Start: Haydon, St Catharine Parish church (Grid ref: ST670158, Postcode: DT9 5JB, What Three Words: downfield.master.surpasses)
Map: OS Explorer 129 Yeovil and Sherborne
How to get there: From Sherborne follow the A30 east and take the firts right in Milborne Port to head to Goathill. Stay on the same road for about 1 mile to reach St Catharine Church on your left.
Dogs: On leads where livestock is present and in accordance with any notices on the walk and The Countryside Code. There are no stiles on the walk.
Refreshments: None on the direct route but plenty are available in the town of Sherborne.

The best place to park is next to St Catharine’s Church. It is a redundant church and privately owned so there is no public access, but it’s a wide part of the road. From the church walk towards the gates of Sherborne Estate. Head on through and follow the road until it splits and take the left hand fork. On reaching some large agricultural buildings, take the footpath that disappears behind the buildings and into the forest. Follow the path around and pass through a large metal kissing gate to enter the deer park.
The view opens up in front of you and Sherborne Castle can be seen below through the scattered oak trees. There is a high chance of catching sight of the large herds of deer as soon as you enter the park. Head down the hill to enter into woodland again and on your left appears the Old Keepers Cottage. A lovely small thatched building that you wouldn’t be surprised to see in a fairytale.

Once past the cottage, continue straight on to exit the deer park through another large metal kissing gate. Follow the bordered track for as far as you can see. Sherborne Castle comes more clearly into view on your right, across the flat fields.
Sherborne has had a castle since the 12th Century. Roger Bishop of Salisbury built a castle to the east of the Town to administer the western part of his large diocese. The bishops later built a hunting lodge, below the deer park, to be able to watch the chase.

In 1592 Sir Walter Raleigh was granted the Castle by Queen Elizabeth. However he struggled to maintain it and with great encouragement from his new wife, he built a new house in 1594 in the deer park. Using the foundations of the Hunting Lodge, he designed it all to the latest fashion of the time. In the garden, Raleigh built a stone seat into the wall beside the road so he could sit and smoke his tobacco, look over his gardens and keep an eye on the passing traffic. The road was the main route to Dorchester until 1856 when the New Road was built. Sir Walter Raleigh fell out of favour at court and the property was seized by King James I.
Sir John Digby acquired Sherborne Castle In 1617 adding four wings, giving the house its present H-shape. Matching it to the design of Raleigh’s. In the Civil War the Digby’s fought for the Royalist cause and the Old Castle was used as the base for their troops. This led to it being demolished by the Parliamentary army, becoming the ruin we see today.

Gradually the old castle deteriorated and the new castle stole its name. The landscape designer Capability Brown was commissioned to install the serpentine lake in 1753 and returned 20 years later to landscape the rest of the grounds, incorporating the old castle as a feature. In-between these dates he was busy designing Milton Abbey’s gardens
The Digby Family still own it today but the Old Castle is managed by English Heritage.

Once past the grounds you skim Sherborne town. The path takes you diagonally across the hillside to eventually meet the road. Cross straight over and down the road to take the small metal gate on the right, just before the railway, to enter the river meadows, known as Purlieu Meadow. On your left sits the river Yeo. Its source is not to far north east of Sherborne, so it is little more than a big stream. However it is also the culprit of huge flooding further downstream covering most of the Somerset Levels, often seen on the news. Also the hill the path has just come down is geographically significant. All the rivers to the north of this hill, Sherborne side, flow into the Bristol Channel. In comparison those with their source on the south side of the hill travel to the English Channel.

Alongside the river on your right is the main London to Exeter railway. Follow it to the road and pass through another kissing gate. Turn left and staying on the pavement follow it over the railway towards the next junction. On your right is Castletown, it is a small settlement that surrounded the original Sherborne castle and still contains some beautiful buildings such as Raleigh’s Lodge. It is worth a little diversion down Castletown Street and over the railway bridge, to admire the buildings and the gothic style church of St Mary Magdalene. Back on the main route, turn right to start heading out of Sherborne.

Between the road and the river sits the old Victorian water mill the development if which saved many lives after the river Yeo contaminated the local system. Take the next left hand turn to then immediately turn right onto a track taking you steeply up the hill. Pass the garage on your left and continue straight on to join a bridleway. Once you have gained some height, the old castle’s ruined gate towers appear behind you, peaking through the tree tops.

Follow the bridleway up the hill to join the A30. Cross the road and continue down another track with a house on your right hand side. When the paths fork, take the permissive path on your right. This follows the gradient of the hill until you turn 90 degrees and are faced with a drop into the village of Oborne. On your left you pass Frogden Quarry, a SSSI rich with fossils.
Oborne is close to the border with Somerset, situated on the banks of the river Yeo. It was first documented in the year 975, when it was known as Womburnan. The name comes from the Old English ‘who’ and ‘burna’ meaning place ‘at the crooked or winding stream ‘. By the time of the Domesday Book in 1086, it was known as Wocburne and then Woburn in 1212 before becoming Oborne in a document of 1479.

As you enter the village you pass the new parish church of St Cuthberts, designed by William Slater and built on this new site in 1862 replacing the older church. On the 7th May 1941, a Luftwaffe bomber crashed into the hillside below Oborne Wood. All aboard died and were buried the next morning in the churchyard, where they lay until their remains were transferred to the German War Cemetery in 1963.

On meeting the road, the Old School on your left, turn right and head back to the A30. Turn right, cross over and turn left passing St Cuthburt’s old chancel on your right, almost hidden in plain site from the busy A30.
Only the 1530’s chancel remains of Old St Cuthbert’s Church as the medieval nave was demolished in the 1860s. It survived a mere six years as a chapel of ease for the monks of Sherborne before the dissolution and bears the crest of Henry VIII above the east window.
Behind the church was a grave that has now disappeared. Robert Goadby, the founder of the Western Flying Post, now better known as the Western Gazette, was buried here in 1778. His grave was marked with a memorial stone, a pine tree planted on top and surrounded by iron railings. The tree was later replaced with an elm tree which, on the bicentenary of his death, was felled after falling victim to Dutch Elm disease. The tree surgery had catastrophic consequences for his memorial, which was completely destroyed in the felling process.


Head to the railway and walk under its small archway to enter into the field. Diagonally cut across to the left to reach another kissing gate and straight across to meet another farm gate. Head up the hill to enter the woods and turn right. Follow the gradient of the hill through the trees to exit facing two imposing stone gate posts and an extensive stone wall.

These grand pillars and urns marks the entrance back into Sherborne estate. Now hidden among the trees and only seen by those that live here, walk here or annually visit the Sherborne Fair, arriving from the north east. The gate posts would have once faced a very different view. Crossing in front is Pinford Lane, it is an old medieval road (or possible older) that connected Sherborne – passing right in front of the old castle via Castleton Street – to Shaftesbury and on to London. It would have been a busy route and any passing traffic would have seen these stone towers. The rest of this ancient route is hard to follow, not only because of its age but because of agricultural and other human intervention on the land. The rather dominating position of the A30 can also distract you from the it’s original path.
Adding more evidence to this ancient track, Roman remains have been found including coins, pottery, brooches and beads.
Head through the gates and on to Pinford Farm. Just before the buildings, turn right into a field, crossing the River Yeo via a footbridge. Climb up the other side and through another large kissing gate, taking you back into the deer park. Continue straight up the hill, probably the hardest part of the walk, and into thicker woodland. Pass some farm buildings on your right and walk around to the left to another gate out of the park. Cut straight across the field and back to the same road you started on to return through the original gates, past the lodge and back to your vehicle.

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