Princes Risborough to Wendover


Leaving habitation behind you, spend the day following one of Britain’s most ancient trackways dating back over 5000 years, through woodland and hills, encountering a remarkable and barely noticed Neolithic burial site; a small gem of a floral nature reserve; a hidden hillfort; and a brush with Chequers, favoured country retreat for Britain’s Prime Ministers for over a century.  Ending on a panorama from Coombe Hill before the descent leads you into the pretty village of Wendover where there are optional alluring and restorative café options for the leg-weary.

Route Summary

Moderate (strenuous in places) / 8 out of 10

6.8 miles / 11 kilometres

OS Explorer 181

Dog Friendly


How to get here


Eat and drink

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The Ridgeway

The Ridgeway is an ancient trackway that is thought to be Britain’s oldest road. Travellers have been using the Ridgeway for at least 5,000 years>>

Whiteleaf Neolithic Burial Mound

This Neolithic barrow, or burial mound, is one of the earliest monuments in southern Britain dating back some 4000 years>>


With a history dating back to Tudor times, Chequers has been the country retreat of the British Prime Minister for over a century>>

Cymbeline's Castle

Cymbeline’s Castle is the remains of a motte-and-bailey castle with evidence of Iron Age, Roman and Medieval occupation>>

Coombe Hill

Coombe Hill is the highest viewpoint in the Chiltern Hills and on a clear day you can see all the way to the Cotswolds>>

Route Map

Begin Walk

Start: Princes Risborough Station


Turn left out of Princes Risborough station taking the slip road up to the main road; turn right on Station Road to follow it slightly up and round, swinging left (crossing over and ignoring the right turn off). Then, after  a further 100m, before the Bird in Hand pub, turn right down Poppy Road.


After a few hundred metres you will join a main road. Taking care, cross the busy road when you can. Now, on the left side of the road, carry straight on ignoring the cul-de-sac on your left and a short distance ahead you’ll see a metal signposted lane to your left: Upper Icknield Way.


Take this left turn – you will follow this for the next 20 minutes.

You will be passing suburban development on your left but can distract yourself from time to time with views of the Chiltern Hills to your right. You should now begin to see the beautiful red kites sailing overhead; they will become a feature of your day. The path you are on is The Ridgeway and will take you to the beckoning hills directly ahead.

Ignoring all footpath’s off, continue straight on.

You will pass across a school entrance (with the school on your left) and soon after cross a suburban road. Continue on following the signposted Upper Icknield Way heading, in a few hundred metres, towards a football ground where the housing on your left ends. With the football pitch now visible through the hedge on your left, you will now encounter a clearly signposted right turn marked The Ridgeway.


Take this right turn to enter farmland with a hedge on your right; you should now just be able to see the grey/white outline of the historic white cross high to your left. For me, this is the start of the walk and, despite the ascent ahead, always provides a delicious pang of expectation and, dare I say it, adventure!  However, you may find yourself having a completely pang-free moment, no matter, press on.

A few hundred metres further on, as soon as the path enters the shrubs and woodland be sure to follow the right-hand track straight ahead and directly upwards.


Shortly uphill, crossing a junction of footpaths, continue straight up following the steps all the way. Take your time…

As it climbs the woodland eventually gives way at a stile to open ground. Passing through, continue up the path directly ahead of you.

For those of you with the capacity for deferred gratification, resist the temptation to turn around and admire the view no matter how breathless you might be.  After a couple of hundred metres you’ll see a very handy topographical stone pillar and just behind it a bench on which you can rest your butt.

You have earned this moment to pause and gaze.


Continue directly into the woods, behind the bench, passing through a metal stile. The path faintly diverges here with a right and left fork – take the lower left fork (it won’t matter if you get this wrong, but this route will make navigation a little clearer).  After 100m you’ll pass through another metal stile to a rising road.

Descend to the road and follow the Ridgeway sign pointing right, uphill, towards a barely visible car park on the opposite side of the road.


After 50m take the signposted Ridgeway bridleway sign on the opposite side, left, up around the car park. With the car park on your right follow the path, signposted, as you continue through the wood.

Look out in a short while for hummocks and hollows in the ground to your right and left which are the remnants of trenches dug by soldiers practising trench digging prior to the First World War. Such a beautiful location in which to prepare for something quite different, so awful and, at that time, unseen –  a poignant thought.

Continue on the signposted route through the trees to emerge after a few hundred metres to a gate leading to another open view.


Pass through the stile and take a moment to ascend the chalky mound immediately to your left: this is the Whiteleaf Neolithic Burial Mound carbon dated as over 5000 years old.


Now, turning your back on the splendid view, head towards a clearly marked signpost pointing you ahead into the trees and then downhill through the metal stile.  (Ignore the descending path on the opposite side to entry point).

The wide path descends steeply between trees appearing to split at one point, ignore this as both paths are OK, just continue straight on downhill where you will emerge after several hundred metres at the side of the Plough Inn, Cadsden: a possible early lunch stop.


On leaving the Plough, keeping left, follow the car track up to the main road which descends ahead, from where it joins the road, after 20 m, look carefully to your right where you will see a gap in the trees and a wooden barrier leading you back onto the signed footpath.


Follow this footpath through the small woodland for  about 100m to emerge in an open rising meadow: Grangelands Nature Reserve.

As you approach the wooden barriers that lead you into the nature reserve you will see the signposted Ridgeway to your left. You can take this path or just as easily head straight in and up through the gate directly ahead. I will navigate you on this latter route to join the Ridgeway in a few hundred metres.

The noticeboard here gives an indication that this meadow is a splendid place in spring and early summer with an unusually diverse variety of flora. Flower hunters could do well to have a neb about here.


Entering the right-hand gate into the rising meadow continue straight ahead and up heading towards a line of woodland on the far side.

Follow the thin and streaky chalky path along the side of shallow ridge keeping straight ahead until within 100m of the trees ahead you will see a clearly visible gate over to your left.

Pass through this gate bearing left along the path to join up, after  about 200 metres, with the Ridgeway.


Following the sign, swing right up through a metal stile onto more open land with shrubs and woodland on your right. Track this path along the edge of the woodland with horse paddocks clearly visible a way off on your left.  More red kites…

After a few hundred metres, the land to your right opens up with the rough meadow enclosed by the wood on three sides.  You may notice posts in the ground further up the slope – the site of a First World War rifle range.

Continuing on your way, the path now rises briefly and steeply ahead and up into the trees; passing through the wooden gate and meeting a wide and ancient ‘hollow way’ at a junction.

Take the signpost right and then after 30m left up through a metal gate. Pass through into a semi-open copse.


Picnic Spot: Look immediately to your left and between small trees you’ll see a grassy mound about 30m away. This has a good view and provides an excellent spot to stop (providing you have something dry to sit on). From here, looking north, you are effectively sitting in what is known locally as the Devil’s Pulpit facing a congregation of beautiful trees spreading out below and beyond.

Returning to the path, continue on straight ahead to pass a wooden post with a small yellow arrow.

Look out to your right for the graceful and sculptural dead tree, and beyond that the rough grassy banks. If you clamber up here, you will see a deep trench on the other side, revealing the ramparts of an Iron Age hill fort, long since lost in the dense wood that covers the top of the hill. In its day, cleared of the trees, the fort would have dominated the landscape with its massive timber walls and defensive trenches.

Re-joining the path, continue your previous direction until you see, ahead and above you, after about 100 m, a quaint metal farm gate, possibly Victorian.


Pass through this gate into a tree enclosed open field, ignore the left diagonal track, to head directly onwards into the far corner, and a gate, passing a happy, spreading beech tree on your right with others behind.

Passing through the gate follow the path which now tracks the edge of the woodland  which is now to your right.


Enter the pleasant wood-wrapped valley that holds the Chequers house and estate. Just beyond  you will begin to glimpse this beautifully positioned and historically significant location –  the setting for many a global deal, bequeathing to us the world that we live in today.  Discuss.

Or don’t.

Make a point of overlooking occasional terse messages from the security services so that you might better appreciate the view of this quietly impressive, shallow valley.

Casting your gaze into the distance in a northerly direction you should see a tall pointed memorial perched high on a hill. For the rest of this afternoon you will be traversing this splendid landscape to reach that point: Coombe Hill.

As you continue along the path (muddy after heavy rain) bordering the estate, the druids and neopagans among you will have spotted that in some of the majestic isolated trees of the Chequers estate hang spectacular clusters of mistletoe.


After several hundred metres your track swings left through a gate to lead you across farmland and through the grounds of the Chequers estate.

More gates will follow as you continue on crossing the driveway, being careful not to trespass and thereby trigger possible death rays being aimed at you by the security services.

Continue on briefly through more open Estate farmland to emerge at a road.


There is a farm shop signposted (Buckmore End) on the other side on your right, ignore this track, because your path is signposted opposite and to the left of the buildings – directly past the house into the trees.

Follow this path directly upward, soon you will cross  ahead over the South Bucks way continuing to rise steadily through mainly beech wood.

This steady climb will, be assured, pay off later.


Continue on, keeping your attention ready for where, a few hundred metres past the South Bucks Way junction, the Ridgeway turns sharp left -signposted – (leaving your uphill path) to now lead you along the side of the hill, still in the wood. The route is very well signposted through this grand old beechwood.



With a shallow gulley on your left, descending just a little, go straight ahead for a short distance to reach another Ridgeway signpost; this bears you sharp right. Follow this onwards (regularly signposted with yellow arrows and acorns) through the beech wood.

You’ll soon cross another bridleway, but you follow the Ridgeway sign onwards and eventually swinging right at another signpost.


After several hundred yards of mostly gentle diagonal ascent through the old wood, the route will lead you directly to a dilapidated wooden fence, which you will pass through to continue following the signposted route; a meadow and barn will be clearly visible through the shrubs on your right.


Continue on until you come to another fence by a driveway, your route is signposted uphill along the road to your right. Although officially the Ridgeway continues several hundred metres further up, you will instantly see on the other side of the road a few metres uphill that common sense has prevailed and walkers take the obvious footpath almost immediately opposite into the wood – this will, after several hundred metres more passing some heroic fallen trees on the way, soon  rejoin the Ridgeway.


Take this route; your path is always straight ahead into the wood. Following the gradually rising ground ahead you will soon pass under a splendid arched bough.

As your path meanders onward, and mostly rising, it will lose some of its definition but this is not a problem as you will soon see bright sky emerging to your right signalling another meadow, the edge of the wood and also the line of your path which tracks the side of the meadow onward. More signposts will soon appear guiding you onward.

With the meadow on your right your path crosses through a semi-circular metal gate and you are pointed by the obvious sign, a sharp left towards the view that you deserve.


Soak up the view and rest if you need it (there are benches).  Walk onward remaining along the crest of the hill with views to the north. ‘Cymbeline’s Castle’ is the obvious whale nosed hill in the near distance off to the (left) north-west.

You will soon reach the rather dramatic monument to the Boer War (the signs pay tribute to a range of British traits: patriotic sacrifice, heartless petty theft and, later, a redeeming generosity).


From here take a little care in choosing your route towards Wendover.

There is a broad, maintained, buff coloured gravel path to your right and a discernible footpath to the left of that and another discernible footpath, also pointing ahead following the side of the hill to the left of that. That is your route; it will have the requisite acorn signpost on it. 


So, take this path, the left-most of the three options.

Your intention is to follow the hill gently onward and slowly down towards Wendover (not to descend sharply to the plain and road visible on your left).

If timing your train is important (and chocolate isn’t – see below) then allow about 40 minutes from here.

You are now going to follow this path keeping to the side of the ridge and broadly maintain your height. You will soon pass through gates and a bridleway which crosses your path. Continuing on ignoring any minor footpath to your left or right.

The chalky/flinty path will continue on gradually losing height for about another 20 minutes.


Shortly past an information board you may see a yellow road and acorn sign pointing left, ignore this, as it will give you an unnecessary deviation from your intended route towards the station. (However if you do take it you will  simply rejoin the intended route further on).


Carrying straight on, and shortly after this, you will encounter a metal gate. Pass through this continuing on with the view ahead opening up a little into scrubland and grass – views of Wendover are beginning to emerge directly ahead of you and slightly to the left.

In this more open area, your worn path will be clear to you; on the left a small black post picks up the acorn and yellow arrow signs again.

Your direction is continuing onwards towards Wendover on the northern open edge of the slope with steep scrubland falling away to your left.

Continue on until the path brings you to a hummocky former chalkpit with steps and wooden railing leading to a gate and then a road.


Cross with care, turn right, heading downhill, passing the sad HS2 planning-blighted cottages on your left.  After ten minutes you will pass above a busy road to reach Wendover Station on your left.

Should you miss the train or just want to extend your day/have a break  you can head on into Wendover – still a good looking village – where there is the immediate consolation of a tapas bar serving coffee and churros on your left and, just past this, a recommended yummy Chocolatiers – Rumseys.

Browse more walks…

Lucky you. I’ve walked several thousand miles of footpaths and city streets to distil out a choice selection of rambles for everyone to enjoy. There is no way of knowing whether a walk is worth doing except by walking the route every step of the way; a lot of terrible walks, dull vistas, and frankly boring trudges have been endured and discarded. Lucky me, I love walking and being outside so it’s all been worth it. I hope you can find the time to explore a route or two.

"Everywhere is within walking distance if you create the time..."

Princes Risborough to Wendover - LOHO Walk

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