An easy walk suitable for all the family with stunning views over the Vale of Aylesbury from the top of Pitstone Hill. The area is also rich in history, having an ancient windmill and two museums dedicated to displaying various aspects of village and rural life over the centuries.
Seasonal walks
Welcome to our Winter Walks collection
The routes on this page have been specially selected from Chiltern Society walks published on our own leaflets, on OS Maps, and on Visorando. They’ll take you to some of the Chilterns’ most loved and iconic seasonal highlights.
The Chiltern Society Walks Leaflets shown below are from our collection of more than 80, which are FREE for personal use and can be found here.
Please note that following the buttons below should either download a PDF to your device, or (depending your settings and if you have the app) open the chosen walk in your browser, in OS Maps, or Visorando.
Gade Valley Route – Jockey End to Gt. Gaddesden
A beautiful walk in the parish of Great Gaddesden in Hertfordshire, passing three beautiful houses. It starts on the chalk plateau at Jockey End and follows the Hertfordshire Way, descending through fields and parkland to the water meadows by the Gade chalk stream.
- 5.1 miles
Lilley and the Galley & Warden Hills
A wonderful walk that starts from the historic village of Lilley and passes through some of the best chalk grassland in the Chiltern Hills. The walk also touches on three major walking trails.
- 5.6 miles
- Stile free
Aston Rowant Route
This short, stile-free walk shows the Chilterns at their best. There are quiet and hidden landscapes, a National Nature Reserve and superb views from the top of the escarpment.
- 3.5 miles
- Stile free
Princes Risborough Ridgeway Partnership Walk
A walk from Princes Risborough using the Ridgeway and the Chiltern Way to visit some of the local highlights.
- 7.1 miles
A Sense of Dacorum
This walk aims to demonstrate that modern Hemel Hempstead and its environs have much more to offer than cynics would have you believe.
- 6.4 miles
- Stile free
Cholesbury Camp
The highlight is a visit to Cholesbury Camp, a well-preserved Iron Age hillfort now managed by the Chiltern Society. You will also discover a fascinating history that includes historic buildings, a generous vicar and a local hero who fought at the Battle of Trafalgar.
- 3.9 miles
Prestwood and Cobblershill Farm
The walk quickly leaves Prestwood and uses some of the less frequented paths to enjoy the beautiful countryside in the surrounding area. The route includes beautiful meadow views, woodland walking, and crosses the stunning glade to Hampden House.
- 5.1 miles
- Stile free
Nettlebed to Maidensgrove Walk
This beautiful scenic stile-free walk is centred on the historic Oxfordshire village of Nettlebed. It features two commons, a nature reserve and the wonderful Chiltern landscape of beech woodlands, chalk grassland and rich wildlife. Take the many opportunities on route to enjoy the great views.
- 4 miles
- Stile free
Henley Hills and Woodland Walk
A lovely stile-free walk that explores the hills and woodlands that overlook the beautiful market town of Henley-on-Thames. The first section of the walk is across high parkland with excellent views, the return is through woodland.
- 4.5 miles
- Stile free
A Penn Circuit
An undulating walk through woodland and arable farmland, via Penn House Estate, Common Wood and Penn Wood.
- 5.7 miles
- Stile free
Ayot St Lawrence
A walk which explores the landscape and history of this special corner of Hertfordshire. It starts and finishes in Kimpton and includes two 12th century churches, a neoclassical church, a park designed by Capability Brown and the house of a famous playwright and author.
- 5.5 miles
Burnham Beeches
A walk suitable for families round the scenic Burnham Beeches National Nature Reserve, which is particularly colourful in spring and autumn, but well worth a visit at any time of year. It can be shortened if required.
- 5.6 miles
- Stile free
River Wye Walk
A short walk from High Wycombe based around the river Wye. Learn about the history of the river, see the work of the “Revive the Wye Partnership” and the place where the Chiltern Society started in 1965
- 5.5 miles
- Stile free