Uffington White Horse in Chiltern Hills seen from above

Best Places to Visit in the Chiltern Hills

Almost two-thirds of the Chiltern Hills Area of Outstanding Natural Beauty is working farmland and foodies can enjoy the local produce on menus everywhere from the historic coaching inns to Michelin-starred restaurants.

Walkers and cyclists won’t be disappointed with the array of trails through the chalky downlands and rolling valleys where wildlife thrives, while Midsomer Murders fans will love visiting the sleepy villages that were used as filming locations.

Indeed, the pace is beautifully slow in the hills, but as you head towards the Thames you’ll find sophisticated towns like Henley that offer a livelier scene.

Berkhamsted castle ruins in Hertfordshire, Chiltern Hills

Berkhamsted, Hertfordshire

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.

A monument at the top of Coombe Hill, looking out over the Buckinghamshire countryside in Chiltern Hills

Princes Risborough, Buckinghamshire

Princes Risborough is a small market town that lies between the Vale of Aylesbury and the western ridge of the Chiltern Hills and is known for its mysterious chalk hillside carving, called the Whiteleaf Cross.

At nearby Coombe Hill, which is the highest point in the Chilterns, you can admire far-reaching views over the Aylesbury Vale and Chequers, the country home of the Prime Minister.

Managed by the National Trust, Coombe Hill is a designated Site of Special Scientific Interest for its chalk grassland and acid heathland. It’s a popular place for birdwatching and in the summer the display of wildflowers is stunning. 

In the countryside surrounding Princes Risborough, there are many prehistoric sites including the Icknield Way which is better known as a multi-use trail suitable for walkers, cyclists and horse-riders. It also links to the Ridgeway National Trail.

Meanwhile, the Phoenix Trail follows a disused railway line for 5 miles through the countryside between Princes Risborough and Thame and is suitable for wheelchair users. Back in the town, there are plenty of shops, cafes and pubs to keep you suitably refreshed, as well as a popular street market held on Thursdays.

Looking across a Barley field to Old Amersham

Amersham, Buckinghamshire

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.

Bekonscot Model Village

Beaconsfield, Buckinghamshire

The Old Town of Beaconsfield with its grand houses, parish church, green and old coaching inns is the historic heart of the town and offers a glimpse of rural England in times gone by.

Along the main street, there are lovely independent shops, restaurants and pubs, while on the fourth Saturday of every month there’s a highly-regarded farmers’ market.

The new part of town meanwhile, offers a good range of shops and, by the train station, you’ll find the popular tourist attraction of Bekonscot Model Village and Railway that opened in 1929.

Nearby, there are some great country pubs including the Royal Standard which was used by Royalists in the 1640s during the English Civil War. Step inside and see the medieval floor tiles and stained glass windows, hunker down in front of the log fire, or relax on a summer day in the beer garden.

Families will love Odds Farm Park where there are activities including feeding baby goats and collecting eggs to take part in.

However, if you’ve come for the country walks there’s an easy circular route from Beaconsfield to Seer Green, with the option to return by train. Burnham Beeches nature reserve, just a couple of miles from Beaconsfield, is also a great place for walking.

Marlow, UK

Marlow, Buckinghamshire

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.

A narrow boat moored opposite Greenlands on the River Thames at Hambleden, Buckinghamshire, UK

Hambleden Valley, Buckinghamshire

Representing the English countryside at its very best, this part of the Chilterns is utterly charming. It’s only a few miles from both Henley-on-Thames and Marlow, and along with the Turville and Wormsley valleys it links the River Thames with the Chilterns.

However, the Hambleden Valley feels wonderfully remote and is perfect for anyone in search of peace, quiet and nature. The sleepy villages of Hambleden, Fingest, Skirmett and Turville, with their pretty churches, quaint country pubs and gorgeous scenery, offer the chance to take it easy.

Midsomer Murders fans can visit an array of filming locations used for the TV series, while if you’ve come for the wildlife, this is one of the best places in England to look for Red Kites – they’re sometimes spotted gliding over Hambleden Brook.

The Hambleden Valley is also great for walking and horse riding too, with the Chiltern Way passing through, while the circular Thames & Chilterns Walk links Hambleden with the River Thames.

However, lovers of fine wine and beer should venture to the Chiltern Valley Winery and Brewery for a tour and tasting of award-winning wines, beers and liqueurs.

River at Henley-on-Thames

Henley-on-Thames, Oxfordshire

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.

Uffington White Horse

Wantage, Oxfordshire

Wantage is a small, but busy market town and was the birthplace of the Saxon king, Alfred the Great, who was born here in AD 849. However, the history of Wantage stretches way beyond the Saxon period and if you want to find out more, pop into the Vale and Downland Museum for an insight into Wantage’s cultural heritage.

There’s a real sense of community in the town and amongst the 17th and 18th-century buildings, there’s a good range of independent shops and places to eat and drink, including some cosy pubs. For evening entertainment there’s The Beacon that runs a programme of comedy, music and theatre nights.

Wantage is surrounded by beautiful countryside that’s popular with walkers and cyclists who use The Ridgeway National Trail to explore all it has to offer.

The Ridgeway is 87 miles long in its entirety, with half of it running through the Chiltern Hills. It largely follows a ridge of chalk hills along an ancient track and about 7 miles away you’ll come across the iconic, prehistoric Uffington White Horse that’s engraved into the hillside.

Ascot, Berkshire

Ascot, Berkshire

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.

Aerial view of Windsor castle, a royal residence at Windsor in the English county of Berkshire

Windsor, Berkshire

The lively town of Windsor on the River Thames has a lot going on for visitors, especially those fascinated by royal history. Windsor Castle, the largest and oldest inhabited castle in the world, dominates the town and parts are open for the paying public to discover.

You can also watch the royal guards marching along the High Street on their way to the Changing of the Guard ceremony at the castle.

From the castle, follow the corridor of elm trees that connects Windsor Castle to Windsor Great Park and its beautiful parkland, deer park, gardens and woodlands.

Back in the town, there are plenty of places to shop and the old Victorian railway station is now a quirky retail space selling everything from designer labels to specialist items.

Alternatively, take a sightseeing boat trip along the River Thames where points of interest include Eton College Chapel, Brunel’s Bow String Bridge and Royal Windsor Racecourse.

However, for family fun it’s hard to beat LEGOLAND® Windsor theme park, that’s not too far from town.

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