Longer Walks in the Chilterns

These walks range between 7 and 16 miles long and include some of our most popular routes. They are likely to take 3.5 to 8.0 hours to complete. They are ideal for curious and more experienced walkers looking to explore remote, unspoilt and less well-known parts of the Chilterns Countryside. You might want to bring a packed lunch or to plan a pub lunch where possible.

Bluebells in a woodland clearing

Watlington Hill - Greenfields and Saxon Roads

A 7-mile walk from Watlington Hill that explores chalk grassland and beech woodlands on the historic landscape of the Chilterns on the border between Buckinghamshire and Oxfordshire.

Chequers from Coombe Hill

Coombe Hill and Chequers trail

This moderately energetic circular walk offers panoramic views across the Aylesbury Vale. You’ll see rare chalk grassland, beautiful woodlands, the pretty village of Ellesborough and the Prime Minister’s country retreat at Chequers. Feel the fascinating history of the Chiltern Hills, inhabited by people for thousands of years.

Small Dean

Chiltern Hills, Valleys and Woodlands Walk

This is an 8 mile (13 kilometre) walk starting in the National Trust’s Bradenham Village and leading you through a mix of chalk meadows, beech woodlands and a variety of farmland.

Ridges and Bottoms walk in Buckinghamshire

West Wycombe: Ridges and Bottoms

This 8 mile walk heads northwest of West Wycombe to some beautiful countryside and woodland with far-reaching views.

Hampden House

The Hampdens Trail

An eight mile walk takes you through undulating farmland and heavily wooded hillsides around the Hampden Bottom valley, one of the least populated and most beautiful parts of the Buckinghamshire Chilterns. You visit remote hillside hamlets and pass through the grounds of the stunning Hampden House.

Watlington Hill in Oxfordshire

Watlington Hill and the Wormsley Estate – An Emblematic Chilterns Walk

This is a 8.4 miles (13.4 kilometres) walk taking you around the National Trust’s Watlington Hill site, Pyrton Hill, Cowleaze Wood and the Wormsley Estate.

Turville village

Hambleden Valley, Turville and Fingest

This 9.5 mile circular walk starts from the village of Hambleden. It crosses the Hamble Brook chalk stream before climbing into the lovely hills and woods to the west of the Hambleden Valley. The walk then descends to the picturesque villages of Turville and Fingest before turning south for a gentle return to Hambleden along the valley alongside the Hamble Brook.

West Wycombe Hill

Chiltern Hills Three-in-One Walk

A scenic walk linking three National Trust properties in the Chiltern Hills: West Wycombe, Bradenham and Hughenden.

Beacon Hill from Coombe Hill

'Exploring the Chiltern Escarpment': a walk between Coombe Hill and Whiteleaf Hill

This 10 mile walk offers a range of panoramic views across the Chiltern Escarpment and the Aylesbury Vale. See a range of historical and archaeological sites, as well as the pretty village of Ellesborough and the prime minister’s country retreat at Chequers. With several important ecological habitats, ranging from rare chalk grassland to archetypal Chiltern beech woodlands, you’ll also pass through the largest remaining area of natural box woodland in Britain.

Turville Heath in the Chilterns

From Chilterns Escarpment to Remote Interior

This is a moderately long walk that begins at Watlington Hill with far-reaching views of the Chilterns escarpment and the Oxford Vale.

Stonor House and Park

A long walk in the Chilterns

This 16 mile circular walk starts at the National Trust’s Watlington Hill site. It drops down and along the Chilterns escarpment then climbs back into the hills. Here you visit pretty hamlets and villages, and the Stonor and Wormsley estates. You also enjoy much remote and unspoiled countryside and woodland. The walk is challenging but hugely rewarding.