If you are considering walking this route yourself, please see my disclaimer. You may also like to see these notes about the maps and GPX files.
I did this circular walk of about 8.7 miles on Monday, 3rd November 2025. It was a route I first walked in 2015, and have walked most years since then in either the clockwise or anti-clockwise direction. This walk went anti-clockwise.
I sometimes park beside the edge of Hawridge Common, close to the Full Moon pub and the road junction with Ray's Hill, but on this walk I chose to use the parking area by the cricket ground in Cholesbury (Grid Reference SP 933071). I started walking about 9.45am, passing the cricket pitch on my left. As there had been rain overnight, I chose to walk down Rays Hill, a road going right from a junction, rather than use a footpath that starts on that side a little before the junction (it can get very muddy and slippery). At the bottom of a valley, I took a footpath on the right. This went through a small enclosure and continued along the valley through a couple of empty sheep pastures.There was then a staggered path crossroads where I turned right then left, the path now running between fences either side. Beyond the fences the path carried on along the right edge of a couple of arable fields, with Cholesbury and then Buckland Common on top of the hillside on my right. After going straight on where a path crossed (part of the Chiltern Heritage Trail), the path continued between hedges, then went half-left across a paddock. On entering a second paddock I continued in the same direction to a gate in the corner. Through the gate, I followed a fence to another gate, through which the path continued half-left across a meadow to reach a minor road. I went a few yards right, then turned down the drive to Dundridge Manor (by a fingerpost).
The start of Rays Hill, with a view of Hawridge Windmill (incidentally Hawridge is pronounced Harridge)
Rays Hill
The start of the footpath along the valley immediately south of Cholesbury and Buckland Common
The footpath along the valley immediately south of Cholesbury and Buckland Common, after I turned right at a T-junction
The footpath along the valley immediately south of Cholesbury and Buckland Common, after I turned left
Further along the same footpath
Further along the same footpath, now near Buckland Common
Where the footpath crosses a couple of paddocks
The last part of the footpath, approaching the road near Dundridge Manor
Buttercups
I went a few yards down the drive, then took a footpath starting on the left. I went straight on when another path went right, soon reaching a wood called Widow Croft. I kept right at a path fork just inside the wood, and carried on through the wood where there was initially much Holly. On the other side of the wood the path stayed heading southwest, crossing a track and running through a plantation (young enough not to be shown on my OS map). The path then crossed a field to a corner of Newsets Wood before continuing on through the wood.
The path from Dundridge Manor heading to Widow Croft
Widow Croft
The new plantation after Widow Croft (not shown on the OS map)
The new plantation after Widow Croft
The new plantation after Widow Croft
Approaching Newsets Wood
Newsets Wood
On the far side of Newsets Wood I turned right along a bridleway which soon followed a hedge on my left as it dropped down into a valley. The bridleway switched to the left of the hedgerow as it started up the opposite hillside. The bridleway then dropped down again into the next valley where it ended when it met Arrewig Lane. Here I went straight on, following the lane uphill.
The bridleway going southwest from Newsets Wood
The bridleway going southwest from Newsets Wood
Looking left from the bridleway, at the bottom of the first valley
The bridleway going up the far side of the first valley
The bridleway descending into the second valley, where it ends (Arrewig Lane continues up the opposite hillside, in the trees)
Arrewig Lane (the name comes from the Saxon for 'way to the fields', apparently)