Whiteleaf Cross and Chequers Circular Walk
This circular walk explores the area around the Prime Minister’s country retreat of Chequers in Buckinghamshire.
The walk offers a mix of woodland paths, open scenery, and far-reaching views across the Chiltern Hills. You can start off from the car park at Whiteleaf Hill near Princes Risborough. You'll then head north east to the historic Chequers Estate set within the rolling landscape of the Vale of Aylesbury. As you walk, you’ll encounter several notable archaeological sites, including a Neolithic long barrow and the remains of an Iron Age hill fort, which hint at the area’s long human history.
Brush Hill itself is a designated local nature reserve, with woodland thought to have existed for over four centuries and a habitat rich in wildlife. Nearby Whiteleaf Hill, also a nature reserve, provides panoramic views over the surrounding countryside and the market town of Princes Risborough. The landscape here is typical of the chalk uplands of the Chilterns, with beech woodland, wildflowers, and glimpses of red kites overhead.
Dominating the hillside is the striking Whiteleaf Cross, a chalk hill figure that has been a landmark for several hundred years. It was first recorded in 1742 by Francis Wise, who linked it to the Saxon king Edward the Elder, though its exact origins remain uncertain. The surrounding area also contains Bronze Age burial mounds dating from around 3500–2500 BC, adding to the sense of history that pervades this distinctive and scenic walk.
Whiteleaf Cross and Chequers Circular Walk Ordnance Survey Map
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Chequers and surrounding countryside. The 16th-century country house has served as the official country residence of the British Prime Minister since 1921. The estate lies in a secluded valley of the Chiltern Hills, near the village of Ellesborough, surrounded by ancient woodland and open countryside. It is approached by narrow lanes and sits within a large, secure estate that remains private, though several public rights of way pass nearby, allowing walkers glimpses of its grounds and architecture.
The house itself is a fine example of Elizabethan architecture, with timber framing, red brick, and stone detailing. Inside, it contains a collection of historical artefacts and portraits connected to past prime ministers and British history, including items associated with Oliver Cromwell. The property was gifted to the nation by Sir Arthur Lee and his wife in 1917, on the condition that it would remain a rural retreat for sitting prime ministers and their families, allowing them rest and privacy away from London.