The Monarch's Way through Winyard's Gap
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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.
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Additional information
Terrain
- Field paths, some roads
Landscape
- Little hills and valleys around high ridge
Dog friendliness
- Generally good but some road walking a bit tiring
Parking
- Lay-by just south of Winyard’s Gap Inn
Toilets en route
- None on route
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...
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Been on this walk?
Send us photos or a comment about this route. Or recommend a route of your own.
Walking in Safety
Read our tips to look after yourself and the environment when following this walk.
Get an AA guide
Explore our range of ‘50 Walks in’ guides - they’re the ideal companion for a ramble.
About the area
Dorset is made up of rugged coastlines, high chalk downlands and a chain of picturesque villages and seaside towns that make up 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. Hidden gems of Dorset can be found down winding, country lanes that lead to snug villages hidden from view.
Nearby places to stay
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Nearby places to stay
Whatley Cottage and The Boathouse
Oozing character and charm, and steeped in history and heritage, Whatley Cottage is a meticulously restored, rural cottage that has everything you need for a romantic getaway to the glo...
Weavers Cottage
Weavers self-catering cottage is a delightful base from which to explore the beautiful Somerset countryside, visit Market Towns, and the five National Trust properties nearby. This is a...
Weavers Cottage
Weavers self-catering cottage is a delightful base from which to explore the beautiful Somerset countryside, visit Market Towns, and the five National Trust properties nearby. This is a...
The Acorn Inn
The Acorn Inn, run by the enthusiastic and experienced management team of Natalie and Richard, is a traditional village pub full of life, laughter and good company, with an award-winnin...
Summer Lodge Country House Hotel, Restaurant & Spa
This picturesque hotel is situated in the heart of Dorset and is the ideal retreat; it's worth arriving in time for the excellent afternoon tea. Bedrooms are appointed to a very high st...
Oxbridge Farm
Oxbridge Farm sits in the rolling hills of west Dorset in an Area of Outstanding Natural Beauty. The bedrooms are well equipped and offer a very good level of comfort. A hearty breakfas...
Croftview House
Set on the 1,200-acre Hinton Park Estate, Croftview is a huge property for groups of up to 26 guests in 13 bedrooms. Life centres on the vast, L-shaped open-plan living space comprising...
Croftview
Set on the 1,200-acre Hinton Park Estate, Croftview is a huge property for groups of up to 26 guests in 13 bedrooms. Life centres on the vast, L-shaped open-plan living space comprising...
Places to eat nearby View all
