A walk linking three of the most picturesque Chiltern villages. Using the Chiltern and Shakespeare ways it takes you on a circuit through lovely scenery with fine views.
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.


Chiltern Ridges Route
A walk from West Wycombe heading towards Radnage Church, before crossing Bledlow Ridge and returning along the ridge to West Wycombe Hill. Some wonderful views, delightful chalk grassland carpeted with spring and summer flowers, and an optional visit to the notorious Hellfire Caves.
- 8.7 miles

Great Offley and Charlton
A moderate stile-free walk The walk starts in the village of Great Offley, heading south-west along the ridge above Hitchin before descending to the small hamlet of Charlton. From there, there is a steady, scenic climb back to Offley.
- 6.1 miles
- Stile free

Berkhamsted to Frithsden
A walk through lovely Chiltern scenery with lots of interest on the way – a Norman Castle, WW1 trenches, a vineyard, canal and more.
- 6.1 miles

Christmas Common & Watlington Hill
This could be described as a Christmas walk for all seasons, or perhaps as a walk of two halves – a lovely woodland adventure or a breathtaking hilltop adventure. The choice is yours.
- 5.1 miles
- Stile free

Studham and Whipsnade
An easy circuit over lovely rolling countryside from Studham Common to Whipsnade taking in a zoo, a tree cathedral, and a 16th century church.
- 4.6 miles
- Stile free

Pitstone Hill & Ashridge
This walk follows the ancient Ridgeway with stunning views from the top of Pitstone Hill, before returning through the beautiful woodland of the National Trust’s Ashridge Estate.
- 6.2 miles
- Stile free

Views from the Barton Hills
This walk starts by criss-crossing the border between Herts and Central Beds, before climbing up the Chilterns escarpment. It then passes a hidden hillfort, meets three major walking routes and provides magnificent views over the surrounding countryside.
- 6.7 miles
- Stile free

Prestwood Route
A wonderful opportunity to combine a stroll round Prestwood Nature Reserve with a lovely walk in the surrounding area.

Metro-Land
This walk visits Rickmansworth and Croxley Green, whose current size and character owe much to the arrival of the Metropolitan Railway. The varied route includes woodland, fields, a moor designated as a Site of Special Scientific Interest, a village green, rivers and a canal.
- 5.9 miles
- Stile free

The Maharajahs Well
This walk gives fine views of the Berkshire Downs and the Oxfordshire plain and takes in the Maharajah’s Well in Stoke Row.
- 8.9 miles

From Chorleywood into the Chess Valley
A stile-free walk that explores the picturesque Chess Valley, the pretty village of Chenies with its Tudor manor house, 15th century church and village green, and finally delightful Chorleywood Common.
- 6 miles
- Stile free

Three Villages Route
An attractive and interesting walk through rolling Chilterns countryside, taking in the historic villages of Turville, Skirmett and Fingest.whose photogenic appeal has made them favourite locations for film and television. Each has a welcoming pub with good food and a garden.
- 5.4 miles