About

The Coombe Hill and Chequers Trail is a rewarding circular walk through some of the most iconic scenery in the Chiltern Hills, combining wide-open views, rare chalk grassland, deep woodland, and centuries of local history. Beginning at the Coombe Hill car park, this route leads you across ancient landscapes shaped by human activity for thousands of years, weaving together natural beauty, cultural heritage and sweeping panoramas over the Aylesbury Vale.

A Walk with Unrivalled Views

Coombe Hill, standing at 260 metres, is the highest viewpoint in the Chiltern Hills. The summit is marked by the striking Boer War Memorial, dedicated in 1904 to the 148 Buckinghamshire men who lost their lives in the South African War. From here, the views are far-reaching and unforgettable; on a clear day you can see across the Vale as far as the Cotswolds. This high point sets the tone for the rest of the walk, which continues through sunlit grasslands and along chalky slopes that support a rich variety of wildflowers and butterflies during the summer months.

Chalk Grassland & Wildlife

The chalk grassland along the ridge is one of Britain’s rarest habitats and a key reason why Coombe Hill is designated as a Site of Special Scientific Interest. In warmer months, the slopes burst into life with more than 40 wildflower species and up to 15 types of butterfly. The landscape is also dotted with anthills created by yellow meadow ants, forming intricate micro-habitats for many specialist plants and invertebrates.

Woodland, Valleys & Ancient Landscapes

As the path descends, you move through shaded woodland and into the pretty village of Ellesborough, with the church of Saints Peter and Paul nestled at the foot of Beacon Hill. This steep chalk hill offers another short but rewarding climb, with spectacular views across the Vale and to neighbouring Coombe Hill.

Beyond Ellesborough Warren—one of only three significant natural box woodlands in Britain—the trail loops towards Pulpit Hill. Here, a small Iron Age hillfort sits hidden among trees, its ancient earthworks offering a glimpse into the lives of the communities who lived here more than 2,000 years ago.

Chequers & National History

One of the walk’s most notable highlights is the opportunity to pass close to Chequers, the Prime Minister’s historic country residence. Originally a 16th-century mansion, the estate has hosted world leaders, monarchs and statesmen for over a century. While the house itself is not open to the public, the trail offers excellent views across the grounds, framed by the dramatic backdrop of the Chilterns.

Nearby, you’ll also pass disused Rifle Butts—former military training sites used from the 1940s to the 1970s—and remnants of wartime activity, including locations linked to Second World War defences that once protected the Chequers estate.

Trail Difficulty & What to Expect

This is a moderately challenging walk, ranging from 6.5 to 7 miles (10.4–11.2 km) depending on the route you take. Expect:

• Steep climbs, including Beacon Hill (with a bypass available)
• Uneven, occasionally slippery terrain in woodland areas
• Narrow paths and sunken tracks
• Expansive open grassland
• Several gates and kissing gates
  Dogs are welcome but must be kept on a close lead to protect livestock and wildlife.

Practical Information

• Start/End Point: Coombe Hill car park, Grid Ref SP 851062
• Duration: 2.5 to 3.5 hours
• Map: A local 1:25,000 Ordnance Survey map is strongly recommended
• Nearby: Chilterns Countryside
• Conditions: Paths can be slippery in wet weather; take care on steep sections

A map of the trail and detailed route instructions can be found through the website linked.

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