Win Green to Tollard Royal … and back again | 6.3 miles

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This is a lovely new variation on one of our favourite old walks – we took almost three hours to slowly enjoy what is a simple triangular route, with two miles of flat walking along the Ox Drove, followed by a gentle two-mile descent, and a steady two-mile climb back to the car. Be not afeared – the uphill section is fi-i-ine!

Start from the (free) parking area on Win Green. Although the route immediately follows the Ox Drove, if you’re new to Win Green we recommend detouring across the grass track over the hilltop to the trees, then joining the Ox Drove from the far side – it’s worth it for the view.

The view from the Ox Drove across Lord Rothermere’s estate, with its tree avenue lit in the sunshine

From there, simply follow the track downhill to the road, then keep going straight until your right turn.

We love the long, easy descent through Rotherley Down – though be warned, there’s a short but sharp uphill near Munday’s Pond (which doesn’t ever seem to actually exist…).

Descending Rotherley Down towards Mundays Pond

Next comes a short, winding wooded drop into Tollard Royal. If you fancy a break, you can detour left to the King John Inn for a pint – just remember, you’ve still got a two-mile climb back to the car!

Once you reach Ashcombe Bottom, don’t be tempted to follow the Wessex Ridgeway towards Guy Ritchie’s Ashcombe House – that way lies a rather long gloomy track followed by a brutal climb from Under Win Green. 

Instead, bear left and begin your gentle ascent on the Hardy Way, soaking up the bright views as you saunter your way back to the car.

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View from Ox Drove across Lord Rothermere’s estate

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circular walk six miles from Dorset Wiltshire border

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Descending Rotherley Down towards Mundays Pond

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