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.
Moderate (strenuous in places) / 8 out of 10
6.8 miles / 11 kilometres
OS Explorer 181
How to get here
Eat and drink
Good footpaths (The Ridgeway). Switchback and hill tops with some short steep sections.
This is just under 7 miles but because of ascents this can feel more like 9 or so.
Trains from St Marylebone to Princes Risborough and back from Wendover.
You will need to buy your tickets – a single each way – for these stations separately as they are on different lines. There is a ticket machine at Wendover Station.
Always check for the train times and availability before leaving.
See Travel Section in Tips and Resources for ways of using your Oyster/Travel Card to Zone 8 to get very cheap fares.
Princes Risborough station
Wendover Station (closed at weekends)
You can break the walk for lunch at The Plough Inn, Cadsden (#9). This is a popular pub and booking is advisable.
Picnic spot with a view at ‘The Pulpit’ (#14).
There are cafes in Wendover at the end of the walk. We like the tapas bar serving coffee and churros on your left as you come into the village and, just past this, a recommended yummy Chocolatiers – Rumseys.
Pubs at the end in Wendover?
Along with the Ridgeway, this ancient route has been posited as one of the oldest roads in Britain, dating back 5000 years , possibly longer. Its physical and name origins are disputed with some proposing that ‘Icknield’ (while having such a guttural Saxon sound) derives from the tribal name of the East Anglian ancient British Iceni. The Iceni are of course mainly remembered not for their trading but for Boudicca’s ferocious revolt of AD60 against Roman rule which ended in the tribe’s defeat and destruction at St Albans.
Like it’s companion path – the Icknield way – the Ridgeway has been a trading and military route for over 5,000 years connecting the ports of the Dorset coast with Eastern England and a world wide web of paths and sea routes to Northern Europe, Scandinavia and the Middle East.
Historians are now beginning to draw our attention to the multifarious nature of international trade that existed in Britain before the Romans and which explains the colourful, cosmopolitan nature of the grave goods – the ivory, jet, jade, jewels and gold etc – found in burial sites across the UK.
The Ridgway’s high open ground and deep wooded slopes have an insistent way of quietly bending our thoughts towards the long ago lives of those in whose footsteps we are following.
With a history dating back to Tudor times, Chequers has been the country retreat of the British Prime Minister since it was gifted to the nation by Sir Arthur Lee in 1917.
Lee noted a new type of politician emerging, one without large country homes to retreat to and in which to entertain foreign dignitaries. Lloyd George, Britain’s first working-class prime minister, agreed. He would; he was already secretly flogging off peerages and knighthoods to raise cash to enable him to entertain on the same level as his ennobled associates.
Lee had more lofty motives, believing that spending two days a week in the “high and pure air of the Chiltern hills and woods” would encourage its inhabitants to rule “more sanely” and help create “a just sense of proportion.” These claims were recently tested to breaking point when Boris Johnson came here to recover from coronavirus infection.
Chequers is therefore somewhere between a sanitarium, an Air Bnb for Britain’s Prime Ministers and an international gathering place for the greatest figures from modern history, including American and Russian presidents – and Bryan Adams.
It must be a great place to relax with its 1500 acre lawns, indoor swimming pool and magnificent library. Carol Thatcher once compared it to a boutique hotel – which possibly redefines our understanding of the meaning of ‘boutique’…
Whiteleaf Neolithic Burial Mound
This remarkable spot has previously been well signboarded and described but at the time of writing (2021) the information board remains missing. However if any reminder were needed of the millennia of human presence stretching all around you on this walk, this mound might help.
Here is the burial site of a man from somewhere between 3,700-3,650 B.C. which, for reference, makes it older than the Great Pyramid of Giza in Egypt. It is believed that the body was buried between two halves of a large split tree trunk and is that of a man of above average height aged about 45 years. Excavations in the 1930s and later have revealed further evidence of a cremated child urn-burial.
Coombe Hill Monument
Erected in 1904 by public subscription, this remains one of the first ever war memorials to individually name fallen soldiers – in this case, over 1400 Buckinghamshire men who died in the Boer War.
The power of monuments to commemorate is clear, but whether they actually change anything is debatable: just 10 years after this impressive structure was raised another 9.7 million young soldiers were being made ready to have their names dutifully carved into memorial monuments across the world.
The monument itself has proved remarkably resilient having been destroyed by lightning twice. In addition the original bronze plaque and decorations were stolen in 1972, presumably to be melted down for scrap, causing much heartache and anger. However strong local feeling and, more importantly action, led to the full restoration of the monument, including adding names missing from the original and misspelt names corrected.
So, a cheery note of collective action to end on and with which to buoy yourself as, with weary legs, you begin the slow descent back to the station with views all the way.
A nearby trig point gives a welcome sense of location to the conclusion of the walk.
Emerging from the woods onto the open side of Coombe Hill, the immediate view to the north and north-west gives a chance to appreciate the elegance of the most prominent hill, over to your left (NW) a whale shaped feature with its distinctive sloping ‘nose’: known locally as ‘Cymbeline’s Castle”.
The associations of this hill with King Cunobilis (c AD9) are very tempting as the times and their tales are intriguing and colourful.
Cunobilis (‘Strong Dog’) and his tribe traded slaves, grain, ironware, hides and hunting dogs in return for oil, fish, wine and other delightful Roman delicacies. His all-conquering sons did well but one of whom, disgruntled possibly by being given the rather nerdy name, Adminius, (possibly from the Brittonic for ‘He who likes spreadsheets’) was banished by his father, so sought refuge with the Roman Emperor. Unfortunately, the Emperor was Caligula.
In what could be one of history’s most extreme examples of getting the wrong end of the stick, Caligula saw the arrival of Adminius as proof that the entire country had surrendered to him. Launching an invasion force he set off for Britain. However, being a slightly troubled chap, Caligula ordered his army to attack waves on their own shoreline and gather seashells as trophies of victory thus ending this most surreal of invasions in total triumph and lots of whelks.
However it is time to confess that these historical connections with Cymbeline are almost certainly a Victorian invention. While others point to the names of local villages: Great Kimble, Little Kimble etc as proof of the link, etymologists disagree.
The hill’s proven past significance is evidenced by the findings of Iron Age, and Roman artefacts, plus evidence of a motte and bailey castle on its summit. That said, even without its mythology, the hill retains an elegance and dignity particularly in afternoon light.
Between Coombe Hill and the castle a distinctive footpath runs at a diagonal across the flat plain below. An easily missed shallow dip in the side of Coombe Hill where it runs steeply down to meet this path marks the edge of an Anglo-Saxon sunken boundary. Look out for tiny figures of other walkers passing on their way across the farmed field.
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 is the remains of a motte-and-bailey castle with evidence of Iron Age, Roman and Medieval occupation>>
Coombe Hill is the highest viewpoint in the Chiltern Hills and on a clear day you can see all the way to the Cotswolds>>
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 second 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 50m left up through a metal gate. Pass through and follow the track now in semi-open woodland.
After about 150m you pass a wooden post with a small yellow arrow. You can carry straight on or use this as your cue to temporarily depart from the path and take the narrow rising grassy ridge to your right -note the gully on the right just behind the ridge. Here you can find a resting and/or picnic spot (one of my favourite spots) by the spectacular sculptural dead tree, to take in the view below the Ridgeway path, down the valley, known locally as the Pulpit.
If you pause on this ridge, behind you’ll see a steep bank forming a deep trench indicating that you are sitting on the ramparts of an Iron Age hill fort. In its day, cleared of the trees the fort would have been walled in timber, enclosed by the ditch and ramparts dominating the surrounding countryside.
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.
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..."
No 1 : Princes Risborough to Wendover
ST MARYLEBONE I MODERATE I 6.8m/11km
Leaving habitation behind you, spend the day following one of Britain’s most ancient trackways dating back 5000 years, possibly much further...
No 2 : Hampton Court to Richmond
WATERLOO/VAUXHALL I EASY/MODERATE I 7.8m/12.5k
A favourite walk bookended by the imposing Hampton Court Palace and the bare remains of Richmond Palace, along the Thames path and through diverse parks and meadows...
No 3 : Three London Parks
REGENT'S PARK I EASY I 5.6m/9k
Easy walking, people-watching in the parks, and chi-chi 'villages' ending on the splendid views and rambling of Hampstead Heath...
No 4 : Newington Green to Smithfield
CANONBURY I EASY I 3m/4.8k
An idiosyncratic trail of visual and historical curiosities taking in radicals, rebels and assorted contrarians along the way...
No 5 : London Bridge to Greenwich
LONDON BRIDGE I EASY/MODERATE I 5.6m/9k
A real treat for the soul, spending an entire walk following the course of the River Thames from the heart of the old City...
No 6 : Eynsford to Otford
I EASY/MODERATE I 6.8m/11km
A perennial favourite to introduce self-identifying 'non-walkers'. Stunning views of the length of the Darenth Valley, an impressive Roman Villa, a 'castle', a 'palace' and three typically Kentish villages...
No 7 : Eynsford Circular via Shoreham
I MODERATE I 8.2 - 9.1m/13.3 - 14.8km
A longer cousin of Walk No. 6, this route follows the lovely Darenth Valley on its western slopes and returns along the valley bottom. A landscape of hills, open views and a riverine return with a choice of picnic, pub or vineyard for the lunch stop...
No 8 : Sole Street Circular
VICTORIA/ST PANCRAS INTERNATIONAL
I MODERATE I 8.8m/14.2km
Continuously undulating chalk hills and farmland welcome you with vineyards and gorgeous valley views, including a welcome and timely lunch stop at a splendid Kentish scene of a windmill and pub overlooking the local cricket pitch...
No 9 : Guildford St Martha's Church Circular
WATERLOO I MODERATE I 7.3m/11.7km
Along the meandering River Wey via an old watermill to an ascent along ancient pilgrim paths under open skies and woodland, tracking the North Downs Way and the Pilgrims' Way, including an aerobic climb to the perfectly located St Martha’s Chapel for a rest and lunch...
No 10 : Greenwich to London Bridge via Limehouse & Wapping