Best Towns and Villages in the Chiltern Hills

Want to find out which are the prettiest villages and towns in the Chiltern Hills?  Discover Country Cottages Online’s list of the best towns and villages in the Chilterns National Landscape and AONB. 
 

 

Which are the Best Towns & Villages to Visit in the Chiltern Hills?

The Chilters are home to a number of charming historical towns and villages.  Below we have highlighted some of the best. 
 

Aldbury

Aldbury is a pretty little village which sits at the foot of Ashridge forest.  This village is unspoilt and a well kept secret.  There is a small village green with a duck pond and a number of pretty oldey worldey style houses.  There are good walks up from Aldbury to Ashridge at the top of the hill where you may be lucky enought to spot deer (particularly when walking early in the morning).

 

Old Amersham 

For historical charm galore, head to Old Amersham.  Old Amersham should not be confused with the nearby town of Amersham.  Amersham is a busy large town with shops and eateries, but little to recommend it for visitors in terms of picturesque scenery. Old Amersham though is a world apart.  Nestled at the bottom of a hill, Old Amersham is close to Amersham but very different in terms of atmosphere and charm.  

Old Amersham is very pretty and features a number of historical buildings which centre around one long very wide elegant high street.  The pavements are mostly cobbled and the high street dates back to the days of coaching inns where Old Amersham was one of the first stop off destinations for journeys between London and Birmingham.  There is an ancient Market Hall which is still used for markets today and Old Amersham’s high street is lined with designer shops, craft shops and restaurants.  There is a museum of an original tudor house from which you can pick up walking tours of the old town on certain days.  Old Amersham is picturesquely nestled in the Chiltern countryside and there are good walks from the town in to the nearby fields and farmlands.

Berkhamsted 

Berkhamsted is a small busy picturesque market town in Hertfordshire, located around 30 minutes by train from London Euston and close to the towns of Tring and Hemel Hempstead.  With an elegant busy high street with plenty of cafes, pubs and restaurants, plus historical attractions and good walks, Berkhamsted is well woth a visit.

Close to the station in Berkhamsted, are the ruins of a castle, which date back to the 11th to 13th centuries.  Another of Berkhamsted’s charms is its attractive canal.  The Grand Union canal runs through Berkhamsted and barges can be seen drifting slowly by, along with ducks and swans.  You can walk for miles and miles along the footpath by Berkhamsted.
 
For more good walks, the National Trust’s Ashridge woods can be found just a few miles from Berkhamsted for those who enjoy quiet forest walks away from it all.

 

Ivinghoe 

Ivinghoe is a small village situated near Ivinghoe Beacon and the Dunstable Downs.   There is a village green and a pretty church in Ivinghoe, as well as a number of Tudor style historical buildings.  For refreshments, there is a charming tea room, plus a cafe that offers bike hire.   

Pitstone Windmill is on the outskirts of town and can be reached by foot but due to the lack of ease of access it is best to drive.

Picturesque Ivinghoe Beacon can be found just outside the village of Ivinghoe.
 

Tring 

Tring is a picturesque market town in Hertfordshire, located around 40 minutes by train from London Euston.  Tring Station is located around 1 mile from the town itself.

Tring's town centre is home to a few restaurants, a scattering of shops and a couple of good pubs.  The beautiful Chiltern Hills skirt around the town of Tring.  The Woodlands Trust’s Tring Park can be reached from the edge of the town and has wonderful walks across the countryside.

Tring also has its own National History Museum with a multitude of stuffed animals, birds, insects, fish and reptiles from Lionel Walter Rothschild’s original private collection.  This museum continues to fascinate both old and young visitors.  Entry is free currently but a donation is requested.

The Grand Union Canal runs by the outskirts of Tring.
 

Wendover 

Wendover is a picturesque oldey worldy town near Aylesbury in Buckinghamshire.  The town is surrounded by the Chiltern hills, giving Wendover something of an alpine feel to it.  Pretty old buildings line the High Street and there are lots of gift shops and restaurants.  One gem on Wendover High Street is the lovely chocolate café where you can enjoy tea and chocolates or chocolate cake.  There is also another independent cafe and a Costas in the town.

Wendover Woods can be found on the outskirts of Wendover, high up on the hills, with amazing views over the surrounding countryside.  There are tracks where you can enjoy a walk or a cycle.  If you like to ‘monkey’ around you may be interested in finding out about Go Ape’s high adrenaline course high up in the trees.  There is a Forest Café where you can buy a welcome cup of tea.

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If you are looking to enjoy discovering some of the prettiest towns and villages when holidaying in the Chiltern Hills, we hope we've inspired you with our best picks.