Section Overview
At 17 miles, this is the longest section in the eastern Chilterns and the most demanding in terms of both distance and cumulative ascent. The route combines long stretches through ancient beech woods with panoramic chalk ridges, multiple Iron Age hillforts, and a series of sweeping views across the Vale of Aylesbury — a classic Chilterns experience from start to finish.
The trail crosses from Oxfordshire into Buckinghamshire early in the section and passes within sight of Chequers, the Prime Minister's official country residence. Facilities are available in Princes Risborough, which lies just off the trail mid-section and provides a useful refreshment stop.
Starting from Watlington
Watlington is a pleasant small market town with a good range of facilities. The trail heads north-east from the town, quickly climbing to regain the Chilterns escarpment above the Watlington White Mark. The views from the top of the escarpment, looking north across the Oxfordshire Plain, are excellent from the very start.
The first few miles pass through typical Chilterns terrain: alternating open ridge with beech woodland, with occasional long views north across the Vale of Aylesbury.
Through the Chiltern Hills
The heart of this section traverses some of the finest beech woodland in England. Ancient, moss-floored beech woods give way to chalk grassland nature reserves and back again as the trail winds along the escarpment. In spring, carpets of bluebells cover the woodland floor. In autumn, the beech trees turn gold and copper in one of the most spectacular displays in the country.
The trail follows sections of Grim's Ditch — the Iron Age linear earthwork encountered in the previous section — through several stretches of woodland. The raised bank and accompanying ditch are particularly well preserved here, preserved by centuries of woodland growth.
Cholesbury & Pulpit Hill
The trail passes close to several Iron Age hillforts in this section. Cholesbury Camp is one of the most unusual — the Church of St Lawrence was built inside the Iron Age earthworks in the 13th century and the village of Cholesbury has grown up within the defensive circuit. Pulpit Hill further east offers panoramic views from its tree-topped summit and is a notable landmark on the approach to Wendover.
Chequers Estate
The trail passes through the perimeter of the Chequers Estate — the official country residence of the Prime Minister of the United Kingdom since 1921. The house, a 16th-century manor in the Chilterns, is not open to the public, but the trail skirts close enough to offer views of the estate from the ridge above. The sense of remote solitude and proximity to the seat of national government makes for an unusual combination.
Wildlife
This section is one of the richest for wildlife on the whole trail. Red kites — successfully reintroduced to the Chilterns in the 1990s — are now a common sight overhead, their distinctive forked tails and russet plumage unmistakable. Deer are frequently spotted at dawn and dusk, and the chalk grassland nature reserves support rare orchids, butterflies (including the chalkhill blue and silver-spotted skipper), and summer wildflowers.
Arriving at Wendover
Wendover is a small town in the Vale of Aylesbury with cafés, restaurants, shops, and accommodation. The town has a railway station on the Chiltern Line with regular services to London Marylebone (around 50 minutes) and Aylesbury, making it an excellent place to break the trail for the night or to end a day walk.
See our Accommodation page for places to stay near Wendover.