Chequers Estate & Whiteleaf Cross
11 August 2025 - Chilterns AONB, United KingdomThis 7.6km walk takes you through both the British Prime Ministers country estate chequers and up some hills with some stunning views across Buckinghamshire. It starts at Pulpit Hill car park slightly north-east of Princess Risborough. However, if you don't have a car, you can walk from Monks Rishbrough train station and join the route part way around.
Chequers Estate
The first part of the walk takes you to and around Chequers Estate. You will know as you enter the estate due to the menacing CCTV cameras and signs warning you not to leave the footpath path (otherwise you will be breaking the Serious Organised Crime and Police Act of 2000). It is clearly marked, and you will walk perpendicular to the house and gardens. The current house that you can see was built in 1565. Just after the first world war, Chequers was given to the nation as a country retreat for the serving prime minister.
As you walk along you will pass over the driveway and be able to see the gate house. From here you get a bit of elevation and can see the house from afar.
Whiteleaf Cross
From Chequers, set off along the Ridgeway bridleway, skirting the edge of Pulpit Hill. At the summit you’ll find the remains of an old fort—perfect for a brief detour if you’d like to extend the walk.
From the fort, the path meanders through the Grangelands Nature Reserve. Soon you’ll emerge at the road and pass the Plough at Cadsden, a delightfully cosy pub halfway around the route. It has good food and refreshing drinks and therefore over the years it has hosted several prime ministers.
Beyond the pub is the walk’s steepest climb until you reach Whiteleaf Cross. From here, the panorama of the Chilterns unfolds before you in all its glory.
A short descent brings you close to the mysterious chalk cross carved into the hillside. Its exact origin remains a mystery, though records mention it as early as 1742. Today it’s preserved within Whiteleaf Hill Nature Reserve.
From this final landmark, the path drops gently, weaving along bridleways back to the car park.