Tring to Princes Risborough: This stretch of the route travels along some of the highest parts of the Chilterns, playing footsie with the Icknield Way cycle trail and passing through many woods, often along wide avenues lined with stately beech trees. At 15 miles/24 km it’s the longest section: it can also be done as two 7+ mile one day walks, as the mid point stop, Wendover, has a station, or it’s possible to stay in Wendover.

Maps: OS Explorer 181 Chiltern Hills North. The sketch maps should be read in conjunction with the detailed map on the OSmaps app here.
Length: 15 miles/24 km.
Difficulty: This is the longest section of the route and includes some of the highest parts of the Chilterns, rising to 840 feet/256m at Coombe Hill. Paths are for the most part on solid chalk but there are some sections that could be very muddy in winter.
Getting there and away
The starting point is Tring station, on the Euston-Milton Keynes line served by West Midlands trains. If staying overnight in Tring, walk back the half mile along Station Road to the Grand Union Canal and join the walk there.
This section ends at Princes Risborough station, on the Marylebone-Birmingham New Street line operated by Chiltern Railways. Accommodation is available in Princes Risborough.
At the midpoint, the route passes Wendover station, on the Chiltern Railways line from Marylebone to Aylesbury, so it can be undertaken as two one day walks of about 7 miles/11 km each.
Along the way
The A4251 crosses the route of Akeman Street, an old Roman road that is thought to be based on an older route, linking Watling Street near St Albans and Fosse Way at Cirencester.
Hastoe has many buildings in the village and nearby erected by members of the Rothschild family who owned the local estate in the 19th century, including the elaborate village hall.
Further sections of Grim’s Ditch run parallel just to the south of the route and can be viewed by walking a short distance south from Hastoe Cross, or by following a parallel footpath (see alternatives below). The route also passes close to two iron age hill forts and two neolithic barrows or tumuli.
The impressive Boer War monument at Coombe Hill is one of the first to honour and name the individuals who died in a war, rather than commemorating a victory.
Chequers is a fine red brick house built in 1565, which was given to the nation in 1921 by the then owners for the use of UK prime ministers.
Whiteleaf Hill has a tumulus or barrow dated to around 3500BC, very early in the Neolithic period and the first of many hundreds along the Ridgeway. Excavations discovered the remains of a single man with extensive pottery grave goods. The entrance was on the west, facing the great view towards the rest of the Chilterns. Many of the barrows along the Ridgeway are in prominent positions like this overlooking a great view.
Directions
Picking up from the station at Tring, head east towards the Grand Union canal. Just before are the steps down to the canal towpath, itself a long distance walking route, but cross the canal and take the road to the left. Past a parking place for cars is a metal gate. Climb gently with Chestnut wood on the right, to reach the A4251.
Cross to the clearly marked route and climb further to the high footbridge over the A41 (not great for acrophobia sufferers). Continue climbing a ridge, cross the road known as The Twist. A dogleg continues the route past Langton wood, swinging round to cross another road then ahead into Bull’s wood (1.5 miles/2.5 km). After a few yards, a wide avenue opens up to the left, following the contour through beechwoods, with fine glimpses of Tring and Tring Park below, eventually emerging to a road at Hastoe Cross (2.9 miles/7 km). A little down the hill, turn right.
The next section is along a road, Church Lane (but not very busy) through the village of Hastoe, passing the village hall on the left. At the next junction continue ahead on Gadmore Lane. At the bend, enter Pavis wood ahead (3.3 miles/12.25 km), once again following the contour. Emerging on a road by a telecoms tower (3.75 miles/6 km), a few yards left go through the gate in front of barns, then diagonally across a field towards trees. Go through another gate to the right of the trees and follow the hedge line to a gate at the far end. Cross the road and take the track ahead by cottages with enormous Jacobean style chimneys.

After Hengrove Wood the Ridgeway now splits from the Icknield Way (4.5 miles/13.5 km), following a wide arc along the contour line through Hale wood and Barn wood. (I prefer the alternative route – see below.). Then it descends rapidly to a narrow track, Hogtrough Lane (6.5 miles/10.5 km). Go right, along this, past Boswells farm. At the main road into Wendover, cross to Church Lane (7.5 miles/12 km).
Continue past the parish church and where the road bends, take the track right by a pond, continuing ahead beside a stream at the edge of a park, following this past the old school to Wendover High Street (7.75 mls), where there are several pubs and cafes, a perfect half way break. This is in fact the only section of the Ridgeway that runs along a main street.
From Wendover, continue past the station then follow the road across the temporary bailey bridge over the HS2 works. A little up the hill take the left turn and then right through a gate where the Ridgeway route is indicated through Bacombe Hill nature reserve (8.5 mls). Climb ahead along the edge of the scarp with wide views to the north, to the Boer War memorial at Coombe Hill (9.5 mls). From here there are fine views to the Chilterns further west, and down below to the left is Chequers.

Continue along the scarp edge now turning south. A dog’s leg takes you to a path through Lodge Hill woods. At the road go right a short way, then left along the footpath beside the entrance to Lodge hill game farm (10.2 mls). Continue through Linton’s wood: the route then turns west (10.6 mls), dropping steeply down a track. At the road, cross to the gate (10.8 mls). You now enter the Chequers estate. The footpath crosses close to the lodge gates, and across the main avenue, and up the field on the other side, to Maple wood. Follow the path round the edge of the wood with views of Chequers on your right, then across an open field to more woods (11.8 mls). The path descends to a gate into a deep hollow way. Follow this to the right a short distance, then go through the gate opposite (12.1 mls), leading to the slopes of Pulpit Hill, prominent on the left (you can climb this to see the iron age fort if you have the energy!). Continue ahead, across another footpath and through the Grangelands and Rifle Butts Nature Reserve. The path continues through scrubby woodland and you emerge onto a road with the Plough at Cadsden to the left (12.6 mls).
Walk round the pub and then up the steep chalk path leading to Whiteleaf hill (13.1 mls), with its fine view over Aylesbury Vale and towards Princes Risborough. Go left through woods parallel to the scarp slope. Now at Brush hill (13.75 mls) go down the ridge through open country and on through a small wood, eventually to a track. Follow this to the left to New road. The Ridgeway continues ahead, but to get to the station, turn right along the wide green towards the centre of Princes Risborough. Cross ahead at the roundabout, left into Bell St, right into the High Street. Follow the road round past the market cross to the parish church, then along Church Street, carrying straight on along a private road, Manor Park avenue, to the station (15.25 mls).

Alternative routes
These three alternatives (indicated in the sketch map) are before Wendover:
(1) Aficionados of Grim’s Ditch can follow a footpath further south that picks up a section of the earthwork.
(2) Follow the Icknield Way Trail. This continues ahead when it splits from the Ridgeway descending through a very deep and obviously ancient hollow way to the Hale, where the route continues along Hale Lane due west (partly it runs parallel behind the hedge line). This is shorter than the Ridgeway route and the first part is spectacular. At the end of the lane, at the main road, go 100 yards/m north to a narrow footpath between houses and gardens that drops down to pick up the path beside the stream to the High Street.

The ancient hollow way on the Icknield Way trail
(3) A third variant is to leave Hale Lane on the footpath soon after joining it and climb along the edge of the woods to the Iron age fort on top of Boddington Hill. From here a footpath descends due west to the outer streets of Wendover, leading to the High Street.
After Wendover, rather than following the Ridgeway through Bacombe Hill, take the hollow way that starts at the same point to the left: (1) on the sketch map. You miss out on the view initially, but follow a beautiful ancient track through beechwoods and then emerge for the view close to the monument.
Breaking the walk
Wendover provides the best stopover of the whole of The Ridgeway, with three popular pubs and many cafes and shops. The Shoulder of Mutton near the station has a good varied menu and a quirky interior. A second stop at the Plough at Cadsden is also possible, about 2.5 miles/4 km from the end.