The Monarch's Way through Winyard's Gap


Winyard's Gap


3.25 miles (5.3kms)

410ft (125m)
1hr 30min

About the walk

In 1651 the rightful claimant to the English throne found himself on the run in Dorset. Charles II had been making for the coast, but was chased back inland. Forced to take a longer route via Yeovil and Mottisfont, he eventually reached Shoreham, where he could catch a ship to exile on the Continent. Charles had an unfortunate inheritance. In 1649, his father, Charles I, was the first and only British monarch to be executed. The young Charles had fought in early battles of the Civil War, but had been packed off to Europe when it became clear that things might not go the King’s way. Part of his exile was spent in Jersey, where his illegitimate son James, Duke of Monmouth, was born.

The Scots proclaimed the young prince King, and invited him home. On 1 January 1651 he was crowned Charles II at Scone Palace. However, the English Parliament was not going to give up power that easily. At the Battle of Worcester that September, Cromwell’s army triumphed, and Charles had to flee. It was another nine years before the mood of the country changed and the ‘Merry Monarch’ could be invited back to take up his throne.

From Worcester Charles fled south through the Cotswolds, reaching the home of the Wyndham family at Trent, on the north Dorset border, where he went into hiding. From here a ship was arranged to take him to France. The King was to rendezvous with the skipper, Stephen Limbry, at the Queens Head pub in Charmouth, disguised as the servant to an eloping couple. Things did not go to plan. Charles was a wanted man and his description had been widely posted. Limbry’s wife became suspicious and, fearing that her husband might be captured, locked him in his bedroom. When the captain failed to show up, Charles moved boldly on to Bridport, escaping from there by a whisker. He made his way back to the Wyndhams via Broadwindsor and holed up for another 12 days, before a second attempt to reach a ship was successful. Today the route of Charles II’s flight is commemorated with a long-distance path called the Monarch’s Way, which leads through Winyard’s Gap. It is ironic that his father had come the same way at the head of an army and in a much more bombastic mood seven years earlier while campaigning in Dorset.

Walk directions

Go through the back of the lay-by. Keep left, then turn up steps to the 43rd Wessex memorial. Return to the lay-by, and turn right along the road. Pass the Winyard’s Gap Inn on your right then, at the junction, cross straight over and walk up the minor road ahead. Sweeping views open out to the west. Keep right, following the lane over the top of the ridge between shoulder-high banks – the sign of an ancient lane. Flat-topped, bracken-clad Crook Hill is ahead. About 0.25 miles (400m) after the lane junction, bear left through a gate, signposted ‘Monarch’s Way’.

Go along the field parallel with the top edge of Chedington Woods, which fall steeply away on the left. Go through a dilapidated gate on the right-hand side of the clearing and bear right through the woods, round the base of Crook Hill, which is up on your right. Cross a stile and bear diagonally left down the field towards the right-hand corner of a wood. The marshy area can be avoided by skirting round to the right of it, along a low fence. On reaching a farm road, turn right. Follow it up to meet the lane and turn right.

After 200yds (180m), on a corner, go left through a gate and hook back down the fence on your left. Go through two gates at the bottom and continue down the field, alongside the top hedge then slightly below it. Twelve Acre Coppice, down to the right, is a lovely stretch of mixed woodland. At the bottom, go through a field gate and cross the stream via a bridge, then go straight ahead up the track. Pass through a gate and keep ahead across a field. Go through another gate, this one with a round water tank beside it, to pass left of a barn, and turn right on the farm road, through Home Farm Dairy. At the lane go straight ahead, passing Home Farm on the left, into the hamlet of Weston.

Just before Weston Manor Farm bypass it by turning right through a gate (blue marker). Rejoin the track beyond the farm, as it heads straight up the hill, with a radio mast topping the ridge ahead. After a short tunnel of trees bear right through a gate along a green track, part of the Monarch’s Way. Stay on the track through two gates. Pass the gravestone of a local woman – the epitaph upon it is well worth stopping to read. Soon pass through a gate and then another to the left of a barn, with ponds down to the right. Walk above Hunter’s Lodge Farm and up its drive to the road. Turn right on the main road and follow it, with care, down to Winyard’s Gap Inn. Turn left here to return to the lay-by and your car.

Additional information

Field paths, some roads

Little hills and valleys around high ridge

Generally good but some road walking a bit tiring

OS Explorer 117 Cerne Abbas & Bere Regis

Lay-by just south of Winyard’s Gap Inn

None on route

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About the area

Discover Dorset

Dorset means rugged varied coastlines and high chalk downlands. Squeezed in among the cliffs and set amid some of Britain’s most beautiful scenery is a chain of picturesque villages and seaside towns. Along the coast you’ll find the Lulworth Ranges, which run from Kimmeridge Bay in the east to Lulworth Cove in the west. Together with a stretch of East Devon, this is Britain’s Jurassic Coast, a UNESCO World Heritage Site and Area of Outstanding Natural Beauty, noted for its layers of shale and numerous fossils embedded in the rock. Among the best-known natural landmarks on this stretch of the Dorset coast is Durdle Door, a rocky arch that has been shaped and sculpted to perfection by the elements. The whole area has the unmistakable stamp of prehistory.

Away from Dorset’s magical coastline lies a landscape with a very different character and atmosphere, but one that is no less appealing. Here, winding, hedge-lined country lanes lead beneath lush, green hilltops to snug, sleepy villages hidden from view and the wider world. The people of Dorset are justifiably proud of the achievements of Thomas Hardy, its most famous son, and much of the county is immortalised in his writing. 

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