Across the Chilterns: Chesham to Wendover

A linear walk from Chesham to Wendover climbing to the top of the Chiltern escarpment with spectacular views over the Oxford plains from the top of Coombe Hill. The Chiltern Hills are the main point of interest - you walk up one side, to the shoulder, then back down to civilisation. The physical nature of the geography and geology makes this walk feel bigger than it is.

Technical sheet No. 27486162

A Chesham walk posted on 06/10/22 by Chiltern Society. Last update : 20/02/23
Calculated time Calculated time: 5h25[?]
Distance Distance : 16.80 km
Vertical gain Vertical gain : 225 m
Vertical drop Vertical drop : 205 m
Highest point Highest point : 261 m
Lowest point Lowest point : 101 m
Moderate Difficulty : Moderate
Back to starting point Back to starting point : No
Walking Walking
Area Area : Chiltern Hills
Location Location : Chesham
Starting point Starting point : N 51.704784° / W 0.611394°
Ending point Ending point : N 51.761961° / W 0.747623°
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Cock and Rabbit Inn, The Lee, Great Missenden


Start: From Chesham Underground Station to Wendover main line station. (HP5 1BP) This walk will follow The Chiltern Link until waypoint (7) of the route.

(A) From Chesham (A) station turn first left down Station Road to the bottom, then left into the semi-pedestrianized High Street. With the clock tower in the market square in front of you, turn right into Church Street.

(1) At the end go left and take the pedestrian crossing. Turn right and follow the pavement round to the left to continue along Church Street.

(2) At the first bend cross into Bury Lane and follow it uphill past the gates to St Mary’s Church signposted to Lower Pednor & Chartridge. Continue ahead with the tree line on the left for 500m to enter a small wood, and on exiting bear left down to a lane (Pednor Road).

Cross over, go through the gate opposite and drop down steps into a field. There are two paths to the right. Take the second one signposted Chiltern Link across the middle of the field to a gate. Go through and bear diagonally left across the next field past a gate and into a lane (Drydell Lane).

(3) Turn right (North-West) along the lane past a bridleway on the left and go round the corner. Turn left past a gate onto a wide bridleway, the sometimes muddy Herbert’s Hole (B). Follow the bridleway along the bottom of the valley for over 2km to emerge at a road junction.

Continue ahead past the junction with Little Hundridge Lane for a few metres and turn right over a stile. Follow the path uphill between fence and hedgerow. The path soon joins a wide track.

(4) Where that bends to the right, turn left (West) through a gate and almost immediately right through another gate. Follow the field edge for 500m to pass through an opening beside a redundant gate. Ignore the path directly ahead, turn left and stay on this path for nearly 800m as it widens and drops down to join a rough lane.

(5) Continue ahead, signposted Chiltern Link, and follow the lane to a T-junction. Turn left and head towards a road. Cross the road and the stile opposite and follow the path into a wood. Stay in the same direction on the wide track for 650m to a gate directly in front. Go through into a field and stay in the same direction along its edge to pass through a second gate and back into the wood. Proceed along the path for 200m to reach a surfaced lane.

(6) Turn right along it for 350m to meet a road opposite The Cock and Rabbit pub. Turn right, then immediately left and follow the road past the entrance to the pub. At the end of the village green (C), take the road in the same direction (North-West) past the entrance to the church (D).

Follow the road round the bend and after 100m turn left over a stile into a field. Walk along the left-hand edge of the field to the stile directly ahead.

(7) Go over the stile, the gravel driveway and the stile opposite. Bear diagonally right to a stile in the corner. Go over that to meet a wide track. Turn left, to leave The Chiltern Link, into a large field with farm buildings visible in the distance. Follow its left-hand edge to go through a gate into a lane (King's Lane).

(8) Turn left along it for 80m to a lane on the right. Do not walk down the sunken lane (Bowood Lane), which in places is too narrow for a car and a pedestrian to pass,  but take the footpath on the left that runs parallel to it. The path emerges into a field, and crosses the route of HS2. See for the latest information about any construction works.

Follow the path along the right-hand edge of the field, under the power lines and onwards as the path swings right to drop down to a hedgerow. Go through and continue to descend to a metal footpath post.

(9) Turn left across one field and to the left of the hedgerow in the next to cross a stile to meet a fast, busy road (A413). Go over the stile, turn left along the verge for 30m and cross the road. Go through the gate opposite and then over the stile into a field.

Bear diagonally right (North-West) across the field to a gate. Go through and bear diagonally left across the next field to a gate in the corner which is on the Chiltern Way. Turn left through this gate and the one ahead.

(10) Stay in the same direction over the railway bridge and, after 30m, turn right into a field and follow its right-hand edge for 200m. Where the field narrows bear diagonally left to follow a path between two fields as it gently rises to a gate. Go through and turn left to the next gate and a lane.

Cross the lane and go through the gate opposite. Go over a horse track and climb the path directly ahead between fence and hedgerow. Go straight over a crossing path and continue uphill to a gate. Go through and onto a surfaced farm track.

(11) Continue uphill on a stony track for 650m keeping right, and where it swings to the left at the top, stay straight ahead over a stile. Follow the woody path for 270m to a junction with a wide track opposite a house called ‘Hampdenleaf’. Turn right along the track and continue ahead, soon leaving the woods and passing between high hedges.

(12) On reaching an uneven tarmac track, continue ahead past cottages and a small church to the crossroads by the pond in Dunsmore. Go straight on along the lane opposite, signposted ‘Dunsmore Village Only’. After the last house (‘The Beeches’) continue ahead on the bridleway ignoring the stile on the left.

(13) Where the bridleway forks, bear left into the wood and stay in the same direction, ignoring all paths to the left and right, for 1km. Continue past where the fence on the right ends and walk between two old metal gates that face each other, resembling a bridge. Stay straight ahead on the footpath for a further 200m to meet a line of trees on a bank. Go over the bank past old fence posts either side of the path.

(14) Great care is needed to ensure the correct path is taken. Do not veer right onto the bridleway that continues along the other side of another tree line but stay straight ahead to follow the sometimes indistinct path through the wood. Pay special attention to follow the arrows marked on the trees and stay in the same general direction to follow the path for 300m to cross a bridleway.

(15) Go through a gap in the wire fence and turn right to a gate which is the entrance to Coombe Hill. Go through the gate and stay in the same direction, keeping to the left-hand side of the open space to meet a gravelled track. Turn right and follow it to reach the monument (E).

(16) Looking back to the surfaced track, take the grassy track to its left – the Ridgeway Path – and follow the acorn symbols. Go through a gate, cross over a sunken lane and up through the next gate. Stay on this wide path for 1.4km as it drops down to a road.

(17) Cross and turn right down the pavement to go over the bypass and railway bridge. HS2 passes under Ellesborough Road and the Ridgeway in a cut-and-cover tunnel. See for information about current construction works.

Either turn left to Wendover Railway Station or continue down into Wendover (F) for some well-earned refreshments and the bus back to Chesham. (A)

We hope you have enjoyed your walk. Please remember to rate the walk and add comments. We are interested in how we could improve the instructions or the route and would like to hear about any issues with paths on the walk.

Waypoints :
D : km 0 - alt. 113 m - Chesham Underground Station
1 : km 0.43 - alt. 101 m - Church Street
2 : km 0.56 - alt. 105 m - Bury Lane
3 : km 1.95 - alt. 118 m - Drydell Lane
4 : km 5.24 - alt. 180 m - Wide track
5 : km 6.07 - alt. 164 m - Signposted Chiltern Link
6 : km 7.16 - alt. 191 m - The Cock and Rabbit pub - The Lee Village
7 : km 7.95 - alt. 197 m - Stile - Gravel driveway
8 : km 8.7 - alt. 207 m - King's Lane
9 : km 9.4 - alt. 166 m - Metal footpath post
10 : km 10.3 - alt. 160 m - Railway bridge
11 : km 11.07 - alt. 189 m - Stony track
12 : km 12.2 - alt. 234 m - Uneven tarmac track
13 : km 12.7 - alt. 240 m - Fork
14 : km 13.95 - alt. 259 m - Arrows marked on the trees
15 : km 14.14 - alt. 260 m - Wire fence - Coombe Hill, Chilterns
16 : km 14.56 - alt. 250 m - Coombe Hill monument
17 : km 16.26 - alt. 162 m - Road
A : km 16.8 - alt. 133 m - Finish

Useful Information

Start & finish: From Chesham Underground station to Wendover main line station. (HP5 1BP)

Terrain: Mostly on well-defined paths and tracks. Some can be very muddy at times. Total ascent 275m/900ft

Parking: Chesham has several car parks and there is the library car park in Wendover High Street

Local transport:
Bus 55 runs between Wendover and Chesham on Mondays to Fridays and both towns are served by many bus routes.
Chesham Underground Station is on the Metropolitan Line to Baker Street and Wendover has main line trains to Marylebone and Aylesbury

Food & drink: Pubs and cafés in Chesham and Wendover. On the walk, The Cock & Rabbit at The Lee

This walk was created for the book "50 Great Walks in the Chilterns" available from the Chiltern Society White Hill Centre, White Hill, Chesham, Bucks, HP5 1AG Tel. 01494 771250. Fax 01494 793745. The book is also available on Amazon

Visorando and this author cannot be held responsible in the case of accidents or problems occuring on this walk.

During the walk or to do/see around

(A) Chesham: There is archaeological evidence to show that there have been people living in this area since 8000BC. The town is known for its four Bs: boots, beer, brushes and Baptists. Most of the buildings in the town and surrounding area were made of local bricks. Between the wars there were 23 brickworks in the Chesham area. (Maybe that should be five B’s!) It was during the 18th and 19th centuries that the town grew with the development of manufacturing industry.

(B) Herbert’s Hole: The origin of this unusual name isn’t known but could derive from ‘Harbour’, a drover’s name for an overnight resting place.

(C) The Lee is one of the most beautiful villages in the Chilterns. Its name derives from the Old English ‘leah’ meaning ‘a clearing in a wood’. The village encircles its large green, and has many beautiful brick houses. One of them is Lee Manor, once home to the Liberty family (owners of Liberty's department store in London). Sir Arthur Liberty bought the last two wooden hulks from the Royal Navy and used timber from them to construct Liberty's 'Tudor' shop facade. Only one ship had a figurehead, that of Admiral Lord Howe, hero of the battle of Ushant in 1794. It was brought to The Lee and planted at the top of the back drive to the Manor. It was moved to its present site at Pipers, a few hundred metres from the green, following the death of Sir Arthur's nephew in 1952. The Lee has been used many times as a location for the TV series Midsomer Murders.

(D) St. John the Baptist is unusual, as it comprises two churches, one from the 19th century and a Grade I listed 12th century chapel of ease. The old chapel is built of clunch, a mixture of chalk and clay with flints, and inside there are medieval murals. In the churchyard there is a yew tree thought to be over 1,000 years old. In the fields beyond the churches is what was thought to be the site of a deserted medieval village. It was the subject of a dig carried out by the Chess Valley Archaeological and Historical Society in 2011 but no building foundations were found. The latest interpretation is that this is an extended manor complex.

(E) Coombe Hill and the monument : Coombe Hill, which has been owned by the National Trust since 1918, is the highest viewpoint in the Chilterns at 260m above sea level. It commands extensive views across the Vale of Aylesbury, as well as towards the Cotswolds in one direction and Ivinghoe Beacon in the other. Coombe Hill is a designated SSSI because of its chalk grassland and acid heathland, where over 30 species of wildflower and 28 species of butterflies can be found. The site is grazed by cattle during the summer so that the grass remains short and the wild flowers can thrive. The monument dates from 1904. It was built in memory of the 148 men of Buckinghamshire who gave their lives in the Boer War (1899-1902). It had to be rebuilt after a lightning strike in 1938, and was later subject to further damage and vandalism, before being re-dedicated after restoration work in 2010.

(F) Wendover is a market town that lies on the ancient Icknield Way and nestles at the foot of the Chiltern Hills. Its name comes from the Celtic term meaning ‘white waters’ which refers to the chalky deposits in the local streams. The parish church of St. Mary's dates back to the 13th century although there are records of an earlier building. During the Civil War, Oliver Cromwell’s troops were camped in the town and some of their graffiti can still be seen at the church. One local legend says that Cromwell himself stayed overnight at The Red Lion Inn and addressed his troops from one of the upstairs windows.

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