Ox Drove Gravel Road – Win Green Summit loop from Win Green

Running trails & routes

Ox Drove Gravel Road – Win Green Summit loop from Win Green

Hard

runners

Ox Drove Gravel Road – Win Green Summit loop from Win Green

01:44

15.5km

240m

Running

Hard run. Very good fitness required. Mostly paved surfaces. The starting point of the route is right next to a parking lot.

Last updated: November 7, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

Cranborne Chase & West Wiltshire Downs National Landscape

Waypoints

Start point

Parking

Get Directions

825 m

Under Win Green

Forest

4.03 km

Tollard Royal Village Pond

Highlight • Natural

A great place to commence and end the circular walk up to Win Green, the highest point in the Cranborne Chase AONB.

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12.2 km

Need a dryer day if you're on lightweight wheels/tyres, great back road with views of wiltshire one side and dorset the other. Links the Chalkes to top of Win Green towards Shaftesbury. Keeps off the main roads for a few Km's!

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14.4 km

View from Ox Drove

Highlight • Viewpoint

14.4 km

Monk's Down

Highlight • Summit

After a steep climb to get here the views are worth it. If you want to drive there is a car park here.

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14.4 km

Gate to Ashdown House Public Footpath

Highlight • Trail

This unlocked gate facilitates access to a little-used public footpath across the Ashdown House property. It is NOT signed as a public path but it definitely is.

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14.8 km

View of Ferne House

Highlight • Viewpoint

Look down to see the beautiful Ferne House and grounds.

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14.9 km

High Point in Cranborne Chase & West Wiltshire Downs

Highlight • Summit

The Komoot app suggests the North South approach path uphill is a bike path but I had to remove bikepacking gear to push up this narrow steep and loose rutted pathway to the top. Good views at the top.

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15.2 km

Win Green Summit

Highlight • Historical Site

Win Green is the highest point in the Cranborne Chase and affords breathtaking panoramic views over Blackmore Vale and the Salisbury Plain. The views even stretch to the Isle of Wight in clear conditions. The summit is crowned by beech trees atop a Bronze Age bowl barrow which can be seen for miles around.

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