Best Places to Visit in the Chiltern Hills

Berkhamsted lies in a valley on the western edge of Hertfordshire, bordering the Chiltern Hills. The town is steeped in history and its Norman Castle, which even though ruined, is a good example of a motte-and-bailey castle.

Follow one of the audio trails to find out more about the town’s history which includes being the site of training trenches for soldiers heading to fight in WWI.

Berkhamsted was also home of the literary great, Graham Greene, and there’s an interesting walking trail to discover places that inspired his work, while in September the town hosts the International Graham Greene Festival. 

Meanwhile, the Berkhamsted Waterways Walk, which takes in the parts of the Grand Union Canal and the River Bulbourne that flow through the town, is a very pleasant way to explore further.

Or, head to the National Trusts’ historic Ashridge Estate for walks and bike rides amongst the ancient woodlands, rolling chalk downland and rich meadows. The fallow deer are part of the landscape here and from June you might be lucky enough to spot fawns.

For a longer bike ride, there’s a circular trail starting from Berkhamsted that passes through the Ashridge Estate and explores some of the northern Chilterns villages.

Like many towns in the Chiltern Hills, Amersham is a town divided into old and new. Old Amersham nestles in the Misbourne Valley, a place of peaceful woodlands, pretty villages and market towns. With half-timbered medieval houses, former coaching inns and cosy pubs, along with the elegant market hall building, Old Amersham brims with character.

Meanwhile, there are fashionable restaurants and independent cafes, alongside shops, that mainly sell clothing, for you to peruse.

Across the fields and on the hill, is the newer part of town, aptly called Amersham-on-the-Hill. This area evolved following the introduction of the Metropolitan Railway and London is just a 25-minute train ride away.

Being in the heart of the Chiltern Hills, Amersham is well connected to a variety of footpaths and cycling routes. One of the loveliest walks is a 6km route along the River Misbourne, which is a chalk stream that provides rare wildlife habitat. Highlights include a stop at John Milton’s house and Chalfont Mill where you might just spot water birds such as snipe and teal.

Marlow is a pretty Georgian market town set beside a wide part of the River Thames. With a stunning backdrop comprising the lush meadows of the Thames Valley and the woodlands of the Chiltern Hills, as well as a vibrant atmosphere, it is the kind of place where everything you could want is to hand.

It’s been an elegant riverside resort since the late 18th century and the main landmark is the suspension bridge that opened in 1832 and stretches across the river to link Buckinghamshire with Berkshire.

Literary figures including T.S. Eliot and Mary Shelley once lived here, whilst Marlow is also home to one of the UK’s finest rowing clubs where Olympians including Sir Steve Redgrave trained.

You can easily spend time strolling around the historic streets of Marlow shopping at the boutiques, relaxing in the wine bars, taking a boat trip or enjoying a riverside walk at Higginson Park.

Marlow is also a magnet for foodies and the park hosts celebrity Chef Tom Kerridge’s ‘Pub in the Park’ festival in the summer, while his Hand and Flowers pub boasts two Michelin stars. If you’re partial to a beer, do also stop by the Rebellion brewery shop to stock up on real ale to sup back at your cottage.

Henley-on-Thames is an elegant Georgian town on the River Thames that oozes style and is famous for the annual Henley Royal Regatta which is an elegant affair.

Many of Henley’s charms centre around the river and one of the oldest boat operators on the Thames, Hobbs of Henley, offers pleasure cruises to Hambleden Lock, as well as rowing boat hire, perfect for a romantic picnic, while private charters are available for special events.

Henley also hosts a Festival of Music and Arts where acts perform on a floating stage, the Henley Fringe Festival and a Literary Festival.

The town itself is a lovely mix of historic buildings including the town hall and market square, while Kenton Theatre is one of the oldest performing theatres in England.

There are many independent shops, great places to eat and lovely tea rooms, but if you like beer you should follow the Brakspear Ale Trail which features 10 pubs.

To experience the countryside, head onto the Thames Path National Trail which runs through Henley, or set out by bike along The Chilterns Cycleway.

Meanwhile, the 16th-century mansion and peaceful gardens of Greys Court, 5 miles from Henley, makes a great day out for history buffs.

Ascot is an elegant town with plenty of shops, restaurants and bars, that sits at the edge of beautiful countryside, is only several miles from Windsor and has quick transport links to London.

However, there is no denying that Ascot is best known for Ascot Racecourse which is one of the finest racecourses in the UK, attracting thousands of people every year who come to watch world-class horse racing.

It was Queen Anne who arranged the first race meeting here in 1711 and so it followed that Royal Ascot was born. Taking place in June, Royal Ascot is the highlight of the summer racing season here and one of the most eagerly anticipated events in the British social calendar.

Set across five days of racing, with important members of the royal family arriving by horse-drawn carriage in a procession that’s been a tradition since 1825, there’s a real sense of grandeur to proceedings. Race-goers dress to impress with beautiful outfits, not forgetting the hats that tradition states must be worn by all ladies on Gold Cup Day (also known as Ladies Day). There are always many spectacular headpieces to see, many of which are nothing less than works of art.