Win Green to Tollard Royal Circular – 8.5 miles. | Dorset Walks

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Win Green Down, the highest point of the Cranborne Chase, is just outside Shaftesbury and always worth a visit – on a clear day you can see The Needles. There are many walks from the top – the easiest being straight along the Ox Drove itself for constantly spectacular views, it is one of the longest and most ancient routes in the country, going all the way to Salisbury. Our favourite route is below: drop off the Drove to walk a circular route through the Rushmore Park to come in the back of Tollard Royal and then a stiff climb up from beautifully peaceful Ashcombe Bottom on the Wessex Ridgeway.

To follow the Win Green to Tollard Royal route using the Outdooractive App, please find the route here.

The route is a straightforward loop on well-maintained paths, taking in ancient tracks and the Wessex Ridgeway. Parking is easy on Win Green, but also available at points along the Ox Drove: you could also start at Tollard Royal (finishing with a pint in the King John!), which would mean a downhill finish rather than the sharpest climb at the end.
*eta – One commenter says they prefer using the Win Green start, but reversing the route to avoid the stiff uphill climb at the end. The dodgy knee dictates downhills are worse, so this isn’t our own preferred solution, but I’m guessing it will be better for many!

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ashcombe bottom walk

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The above images were the few taken on a re-walk of the original route in August – it’s great to do at any time of year, but is truly spectacular in summer sunshine! The below images give more of an idea of various parts of the route, but are rather dull by comparison as they were taken in early spring …

Win Green to Tollard Royal Circular Walk

Following the ancient track down into Tollard Royal (you can just make out the church ahead). There were a lot of Yew trees on this track – am I the only person to greet them with “Hello Yew!” and a gentle pat as I pass? – Ed”

Win Green to Tollard Royal Circular Walk

“The quiet airy valleys of the Rushmore Estate are always a pleasure to stroll through, even on a flat grey March day”

Rushmore Golf Course Waymarker

“The waymarkers on Rushmore Golf Course are not easily spotted (far right of picture) – check your map and be confident. And simply follow the fence line!”

Win Green to Tollard Royal Circular Walk

“The view of Rotherley Bottom from the Ox drove”

Win Green to Tollard Royal Circular Walk

“The last climb up from Under Win Green. Yes, C is often that far ahead on the uphill stretches!”

Every month in the BV Magazine we publish a Dorset walk in the beautiful Dorset countryside under the heading ‘Take a hike’. Not always in the heart of the Blackmore Vale perhaps, but always within reach for a day’s walk.

Above all, we hope you enjoy reading about the walks that we do and enjoying the pictures of course, but if you are taking them on yourself, we would love to receive your feedback on how you found the individual route and any suggestions you might have. Oh and of course we would love to receive your pictures to share as well!

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