15 Best Walks in the Chilterns (Hikes & Nice Walks)

15 Best Walks in the Chilterns (Hikes & Nice Walks)

By will

Are you looking for an escape from the hustle and bustle of everyday life?

A chance to get away from it all and reconnect with yourself and nature?

Then why not explore the Chilterns, an area of outstanding natural beauty located in South East England?

With its rolling hills, lush meadows, and captivating rivers, it’s no wonder that the Chilterns are so popular with hikers and walkers alike.

1. Ashridge Estate Boundary Trail

Sign for Ashridge Estate Boundary Trail
Photo by David Hawgood

The Ashridge Estate Boundary Trail is one of the best walks in the Chilterns.

Spanning seven miles, it takes in rolling hills, meadows, and woodlands that stretch the length of this ancient royal hunting ground.

Every step offers a new discovery – from picturesque villages to Iron Age hill forts and beech woods.

There’s also plenty of wildlife to spot, making it a great walk for nature lovers.

The trail is well-marked, with plenty of clear paths and signage throughout, making navigation easy even for those unfamiliar with the area.

There are also several benches along the way where you can take a break, enjoy the views, and reflect on your journey so far.

The route can easily be completed in a day but if you’d like to take it slower there are many places to stop off and explore further.

All in all, this is an ideal walk for anyone looking to escape the hustle and bustle of city life and unwind in beautiful countryside surroundings.

2. Chess Valley Walk

Chess Valley Walk
Photo by John Slater

The Chess Valley Walk is a great way for visitors to explore the stunning countryside of the Chilterns.

This picturesque walk follows the river Chess and takes you through some of the most beautiful scenery in England.

You’ll find lush meadows, winding paths, ancient woodlands, and rolling hills – all perfect for a leisurely stroll.

It’s easy to lose yourself in this peaceful valley, where time seems to stand still.

As you make your way along this relaxing route, you’ll have plenty of opportunities to spot wildlife such as deer and wildfowl.

And don’t forget to look out for the ruins of old cottages that dot the landscape.

The Chess Valley Walk is a wonderful experience and one that will stay with you long after you’ve returned home.

3. Chiltern Heritage Trail

Chiltern Heritage Trail
Photo by Shaun Ferguson

The Chiltern Heritage Trail is a stunning walk through the Chilterns, one of England’s most beautiful areas of natural beauty.

From rolling hills to lush meadows, this trail takes you through some of the most breathtaking spots in the region.

Along the way, you’ll pass quaint villages and pubs, and get a chance to marvel at some of England’s oldest churches.

The trail stretches from Chesham to Wendover and is divided into two parts: a northern loop that winds around Chesham, Amersham, and Little Missenden; and a southern loop that goes through Wendover, Wendover Dean, and Dunstable Downs.

The northern loop is especially scenic as it passes through picturesque woodlands, fields full of wildflowers, undulating hillsides, and breathtaking views across the countryside.

You can also spot plenty of wildlife along the way – look out for red kites circling overhead or deer grazing in the fields!

As you make your way around the southern loop there are plenty of opportunities to take a break at one of the traditional pubs or village shops.

At Dunstable Downs, you can even try your hand at kite flying!

The whole walk usually takes around five hours – so don’t forget to pack enough snacks to keep you going!

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4. Whiteleaf And Chequers Circular

The Whiteleaf and Chequers Circular is one of the best walks in the Chilterns, offering stunning views and a great way to explore this beautiful region.

Starting from Princes Risborough, the trail winds its way through forests and hills, with plenty of opportunities for wildlife spotting.

The route takes you up to Whiteleaf Hill for breathtaking vistas across the Chiltern Hills before descending into Coombe Hill Meadows.

Here, you can take time out in a tea room or just enjoy the peace and tranquility of the meadows.

Next, you’ll make your way to Chequers Estate where you can soak up its history and admire its beautiful gardens.

There’s also an opportunity to learn more about this former residence of British Prime Ministers.

As you wind your way back towards Princes Risborough, there will be plenty of chances to take in more spectacular views that form a fitting end to an unforgettable day out.

5. Beacon Hill

Beacon Hill is one of the most breathtaking walks in the Chilterns.

A short drive from London, this National Trust property offers a variety of trails that span across the rolling hills and woodland.

The area is abundant with wildlife, making it a great spot for nature lovers looking to explore.

The views from the summit of Beacon Hill are spectacular; on a clear day, you can see miles into the distance.

You can follow one of the many routes up to the top, or simply wander around at your own pace and take in all the beauty and tranquility of this special place.

Whether you’re looking for an easy stroll or a more challenging hike, Beacon Hill has something for everyone.

With its stunning scenery and abundance of wildlife, it’s no wonder why so many people come here for a peaceful escape from city life.

Come and experience it yourself – you won’t regret it!

6. Pitstone Common

Next up is Pitstone Common, a picturesque area that offers yet another opportunity to explore the sublime beauty of the Chilterns.

This charming spot lies just outside the village of Pitstone and provides breathtaking views across some of England’s most idyllic countryside.

Here, visitors can enjoy a leisurely stroll or an invigorating hike while taking in the fresh air and stunning scenery along the way.

Pitstone Common is filled with lush meadows, forests, and heaths, giving you plenty of secluded spots to take in the views.

Throughout your journey, you’ll be able to admire wildflowers in bloom as well as native wildlife such as hares, birds, rabbits, and deer.

As you wander around this peaceful landscape, you may even find yourself pondering life’s wonders or simply admiring nature’s beauty.

The perfect destination for those looking to escape from everyday life, Pitstone Common is sure to leave an indelible impression on all who visit.

7. Pegsdon And Deacon Hill

Pegsdon and Deacon Hill offer a spectacular walk for those seeking adventure in the Chilterns.

Starting from the village of Hexton, you can wind your way up Pegsdon Hill and onto the smaller Deacon Hill.

The trail is well-marked, with plenty of signs pointing the way.

Along the route, you’ll be rewarded with breathtaking views across the countryside, as well as spotting a variety of wildlife.

On a clear day, you’ll be able to see all the way to London.

The paths are easy to follow and take roughly four hours to complete in full.

There are plenty of places to stop along the way for lunch or a rest break; however, it’s worth noting that some parts of the walk can get quite steep.

Bring along some sturdy walking boots and plenty of water to make sure you’re comfortable throughout.

This is an ideal trip for anyone looking to escape everyday life and find some peace in nature’s beauty.

If you’re feeling adventurous, why not take on this challenge? It’s sure to provide a sense of freedom that will stay with you long after your journey is over.

8. Hurley Loop Walk

The next hike on our list is the Hurley Loop Walk.

This walk takes us away from the Chilterns in a southwesterly direction, bringing us to the picturesque village of Hurley in Buckinghamshire.

The route follows the banks of both the River Thames and River Loddon, providing stunning views of these rivers as they meander through the countryside.

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This 8-mile walk is a great way to enjoy some fresh air and take in some lovely scenery.

As you traverse across fields and meadows, you’ll encounter charming old villages and plenty of wildlife along your journey – with deer being particularly plentiful near the rivers.

Along this route, we also come across two historic sites: Temple Island, which was once home to an Augustinian priory established in 1233; and Hurley Lock, built by Thomas Telford in 1810.

These are just two fascinating stops along the way for those looking for something extra special during their hike.

9. Wendover Loop

The Wendover Loop is a stunning seven-mile walk through the rolling hills of the Chilterns in Buckinghamshire, England.

This loop takes walkers through some of the most breathtaking scenery and beautiful nature in the area.

Starting in Wendover, you’ll wander along the chalk hillside before reaching Coombe Hill and its incredible views over Aylesbury Plain.

As you make your way back along The Ridgeway path, look out for raptors soaring overhead and wildflowers carpeting the fields below.

Along with all this natural beauty, there are plenty of historical monuments to explore including Neolithic earthworks at Coombe Hill and an Iron Age fort near Princes Risborough.

The walk also passes by many picturesque villages with quaint pubs, traditional tea rooms, and independent shops supplying all sorts of local produce.

For those seeking a peaceful escape from city life, the Wendover Loop provides a perfect opportunity to reconnect with nature and enjoy some fresh air while surrounded by stunning landscapes and rich history.

10. Chenies To Sarratt

The Chenies to Sarratt walk is the perfect dose of the countryside and historical exploration.

Starting at Chenies Church, the route offers stunning views of the Chiltern Hills before winding through the picturesque villages of Latimer, Chesham Bois, and Hawridge.

As you make your way along this 6-mile stretch, take time to explore all that this part of England has to offer.

Stroll past ancient churches, old stone walls, and a variety of wildlife as you meander through the beautiful landscapes.

Visit the quaint village of Latimer for some local history or simply relax in the grassy meadows that line the path.

The tranquil atmosphere here will make you feel as though you’ve stepped out of reality and into a world of freedom.

Enjoy every moment as you journey through this breathtaking part of England.

11. Medmenham

From Chenies to Sarratt, the Chiltern Way delivered stunning views of the rolling hills and lush woods.

Now, we take a short walk from Sarratt to Medmenham, where we’ll discover a truly magical place.

The journey between these two villages is mostly flat and easy-going and follows an old road that winds through fields of gorgeous wildflowers.

Along the way, you’ll be amazed by the many varied landscapes that this area offers.

From meadows filled with vibrant blooms to dense woodlands bursting with life, it’s no wonder why this walk is so popular amongst locals and visitors alike.

As you reach Medmenham, you’ll find yourself surrounded by tranquillity.

The village itself is steeped in history – from its ancient church to its country pub – but it’s also full of life thanks to its many small businesses and friendly locals.

Whether you choose to explore or simply soak up the atmosphere, Medmenham provides a wonderful escape for those looking for some peace and quiet away from the hustle and bustle of modern life.

12. Coombe Hill To Chequers

The popular Coombe Hill to Chequers walk is a picturesque stroll through the Chilterns area.

It’s an ideal route for those seeking a leisurely, yet rewarding outing.

The walk takes you along a ridge that overlooks the Vale of Aylesbury and the surrounding countryside.

As you wander along, you’ll be treated to stunning views of rolling hills and woodlands.

Along this route, you’ll come across plenty of wildlife and wildflowers, as well as ancient woodlands and quaint villages.

You might even catch sight of deer grazing in the fields!

You can take your time to soak up the beauty of this unspoiled area or make use of the many benches along the way to pause and admire your surroundings.

This delightful walk is sure to make for an unforgettable experience – one that will leave you feeling refreshed, invigorated, and re-energized.

Whether it’s a peaceful stroll or an energetic hike, there’s something special about being surrounded by nature so close to home.

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So why not grab your walking shoes and head out on this delightful journey through nature?

13. Hambleden

Hambleden is a picturesque village in the Chilterns, renowned for its ancient bridges and spectacular views.

The village is surrounded by rolling hills and fields of wildflowers, making it an ideal spot for long, peaceful walks.

One popular route takes hikers from the village center along the Hambleden Valley, past the river Thames and out into the surrounding countryside.

This walk offers breathtaking views of the surrounding area, with plenty of interesting wildlife to observe along the way.

You can also explore local woodlands or take a stroll around one of the many quaint villages nearby.

If you’re looking for something more adventurous, you can head to nearby Henley-on-Thames and take part in some water sports or take on one of their challenging hikes.

Whether you’re after a leisurely stroll through nature or an adrenaline-pumping adventure, Hambleden has something to suit everyone’s taste – perfect for those seeking peace and relaxation in one of England’s most beautiful regions.

14. Little Marlow Walk

The Little Marlow Walk is a delightful and tranquil journey through the Chiltern Hills.

Starting in the market town of Marlow, you’ll wander through lush meadows, picturesque villages, and countryside full of wildlife.

The charming landscape is perfect for an afternoon stroll, with its rolling hills and idyllic views.

It’s a great way to explore this beautiful area of England and get away from it all for a while.

The route takes about two hours to complete and provides plenty of chances to take in the scenery.

You’ll pass by historic churches, charming cottages, and woods full of wildflowers, streams, and fields.

This is truly an enchanting experience that will make you feel at peace with nature.

At the end of your walk, you’ll be rewarded with stunning views across the Chiltern Hills – a fitting way to conclude your journey in this beautiful part of England.

15. Bourne End Circular

The Bourne End Circular is renowned for its picturesque views of the Chilterns.

With plenty of rolling hills, thick forests, and serene meadows, it’s no wonder why this particular walk has been so popular.

The path starts in the town of Bourne End, making it easily accessible to any traveler.

Along the way, you’ll pass through numerous quaint villages and take in stunning sights of nature.

As you make your way up some of the steeper inclines, you’ll be rewarded with breathtaking views across the countryside.

From Bourne End, follow a footpath that runs along the edge of a wood and then onto a scenic track that follows an old railway line.

You’ll soon come to a bridge that overlooks fabulous views over fields and farmland.

This is where you can take a break from your journey and soak up some stunning scenery as far as the eye can see.

After crossing the bridge, you’ll continue on until you reach a viewpoint at Bledlow Ridge where you can enjoy panoramic views over Buckinghamshire before heading back down again toward Bourne End.

This hike is ideal for anyone looking to get away from it all and explore some of England’s most beautiful countryside while taking in some fresh air and peace of mind; allowing travelers to find their own little slice of freedom amongst nature’s finest scenes.

It’s a great opportunity to appreciate all that nature has to offer – so gather your friends or family and head out on this unforgettable adventure!

Best Walks in The Chilterns – Final Thoughts

I have explored some of the best walks in the Chilterns and I’m sure you’ll enjoy them as much as I did.

The scenery is stunning, with rolling hills and picturesque villages.

Whether you’re looking for an easy stroll or a more challenging hike, there’s something to suit everyone.

I particularly enjoyed the Chess Valley Walk, where I was able to take in views of the river Chess and its surrounding countryside.

The Chiltern Heritage Trail also offers stunning views and a great opportunity to learn about the area’s history.

The Chilterns is a fantastic area for walking, so if you’re looking for a great day out why not head down there?

With fifteen of the best walks listed above, you’re sure to find something that suits your needs.



What are some easy walks in the Chilterns?

Some easy walks in the Chilterns are Beacon Hill, Pitstone Common, and Harlock Nature Reserve.

What are the best circular walks in the Chilterns?

Some of the best circular walks in the Chilterns are Chequers circular, Homefield Wood circular, and Chiltern Hills circular.

What are some good family walks in the Chilterns?

Some good family walks in the Chilterns are Amersham to Little Missenden, Ashridge Estate Walks, and Woodland Walk.

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About the author

Will is an avid hillwalker and traveler. You may find him surfing in Cornwall or hiking in the Yorkshire Dales.