by Janis / 0 comments - Orginally published:12th April 2022

Exploring Chartwell, Hever, Chiddingstone and Edenbridge along the way

There is so much to discover in this relatively short Kent road trip. From a Prime Minister’s family home of Chartwell, charming picture-postcard villages and a magnificent castle fit for a King. And that’s prior to us visiting the surrounding historic towns of Westerham and Edenbridge.

The entire circular mini road trip is only around 23 miles (37km). As it is just a stone’s throw from the M25, it would be incredibly easy to explore at the weekend.

If you’re a National Trust member, don’t forget to bring your card, as there are some true delights to be found in this region of Kent. Check out the details further down this post.

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A brick-built triple arch within the Rose Garden at Hever Castle
Archway to the Rose Garden in Hever Castle

Our Westerham Loop Road Trip Destinations

We'll be discovering the delightful country residences of Chartwell and Hever Castle and popping into the quaint National Trust village of Chiddingstone. We’ll also be exploring the historic towns of Westerham and Edenbridge along the way.

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We chose a circular route around this historical region of Kent, starting and ending in Sundridge. Sundridge can be accessed very easily from the M25 (jct. 5) along the A25; the road trip’s entire loop is only around 23 miles (37km).
The A25 road weaving its way past historic red tiled buildings on the edge of Westerham in Kent
The A25 on the edge of Westerham
Okay, so without further ado, let’s buckle up and hit the road.

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Discover Emmetts Garden

A National Trust gem

Once you leave the M25, travel the short hop along the A21 and then west on the A25 to Sundridge.

Sundridge is an attractive village in Kent with an antique shop to rummage around and a relaxing country pub to enjoy.

From Sundridge, head south along Church Road towards Ide Hill; you’ll spot on your right Emmetts Garden. This hillside garden is your first opportunity to break out your National Trust membership. It is open all year round. They hold events through the spring and summer.

The lush rockery garden at the National Trust Emmetts Garden in Kent
The Rockery at Emmetts Garden

As you continue winding across the lush Kent countryside, you pass through the charming village of Ide Hill with its welcoming village green. Nearby Ide Hill is the Bough Beech Reservoir, a nature reserve managed by Kent Wildlife Trust.

Continue to head south; the next stop is the beautiful National Trust village of Chiddingstone.

Map, guides and more

This region of Kent is ideal for hikes as it is close to the North Downs (AONB), an Area of Outstanding Natural Beauty and High Weald. To explore the trails in this region of Kent, the Ordnance Survey map that will help you along the route is no. 147, ‘Sevenoaks & Tonbridge’.

Alternatively, why not purchase and download the OS Maps App, which covers all of Great Britain.

When you arrive at Chiddingstone village parking, is very limited along the short High Street, and respect should be given to its residents. There is parking in the nearby Chiddingstone Castle for a small charge.
Half-timbered Tudor houses and shops on the High Street of the National Trust Chiddingstone village in Kent
Chiddingstone High Street

Chiddingstone is unique in that the entire village is owned by the National Trust. The tiny cobble-stoned one-street village is one of the oldest in Kent, and what it lacks in size, it makes up ten-fold in charm and character.

The stunning timber-framed Tudor dwellings are exceptional and lovingly cared for by the National Trust residents. Chiddingstone is mentioned in the Domesday Book of 1086, which was completed by order of William the Conqueror.

A wooden bridge leading to the 19th Century Chiddingstone Castle on a bright spring day
Chiddingstone Castle

The first historic home in Chiddingstone was built in the mid-15th-century, shortly followed by the Castle Inn where you can enjoy lunch today. Take a stroll through the gates by Castle Inn, and head up to the eye-catching Chiddingstone Castle on the hill.

Chiddingstone Village is free to visit.

If you're intrigued by Kent's weird and wonderful history, or all unusual stories around the county, then take a peek at "Kent's Strangest Tales".

You won't be able to put it down, you can pick it up for your Kindle or in good old paperback.

We’re now arching round north through Bough Beech and south to Hever and its fairy-tale castle. Hever is a tiny, picturesque village; however, its main magnificent attraction is Hever Castle and Gardens, the childhood home of Anne Boleyn.
The entrance across the moat to Hever Castle in Kent
The entrance across the moat to Hever Castle

Hever Castle is beautiful all year round, and the double-moat surrounding the 13th-century castle makes it magical. It’s quite breath-taking when you first see it from a distance at the brow of the hill.

Not only are you able to visit the medieval castle, which has over 700 years of incredible history, but you can also explore the 125 acres of award-winning gardens. The yew maze is great fun to get lost within and see if you can spot the giant topiary chess set.

I loved strolling around the quintessentially English Rose Garden and the stylishly classic Italian Garden. At the far end of the Pergola Walk, you’ll discover the delightful collonaded Loggia overlooking the 38-acre lake.

Rowing boats moored up on the shore of the lake at Hever Castle with its Italian styled Loggia in the background.
Boats for Hire
There are events taking place all year round at Hever Castle. If you visit during the spring and summer months, you can even venture out to the boating lake.

We have created a little YouTube video of  Hever Castle.  Why not take a look?

Also, why not subscribe to our YouTube channel and get the latest clips as we post them?

Where to stay in Hever

- Hever Castle Luxury Bed and Breakfast - This is your chance to stay in the beautiful grounds of Hever Castle, fit for a King. This luxury accommodation is stunning, stylish and relaxing.
- Beautiful Countryside Bedroom - Is located around 1.7 miles from Hever Castle. It's set within beautiful tranquil grounds; the room has a garden view and terrace.

Our Kent road trips

If you’ve fallen in love with the county of Kent, we’ve created a few more road trips around the “Garden of England” that we believe you will enjoy too.
Jumping back in the trusty steed and we’re heading northwest to the delightful town of Edenbridge. Drive along Hever Road, and you’ll join at the south end of Edenbridge High Street. Journey along the High Street, and you’ll find the Market Yard car park, which is free.
The Eden Valley Museum in the historic Church House on the High Street of Edenbridge
The Eden Valley Museum in Edenbridge

If your timings are perfect and you arrive in Edenbridge on a Thursday, there is a small market in the car park which sells some delicious local produce.

The old town of Edenbridge has many beautiful medieval timber-framed buildings, one of which houses the Eden Valley Museum.

A planted hand cart in the courtyard at the back of the Eden Valley Museum in Edenbridge
The museum courtyard in Edenbridge

Edenbridge is a relatively small town with the usual modern facilities; however, it still possesses the charm of an old English town. You’ll find plenty of independent stores. One that particularly caught my eye was the local hardware shop selling everything for those little DIY projects.

Our next stop is to Chartwell, the splendid family home of Sir Winston Churchill via Four Elms.

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Head north out of Edenbridge along Station Road and turn right onto the B2027. On reaching the pretty village of Four Elms, turn left at the lovely village duck pond and briefly journey along the B269. Then right onto Mapleton Road for 2 miles until you reach Chartwell.

Chartwell is managed by the National Trust, so, once again an excellent opportunity to use your membership card.

The rear view of the red-brick Chartwell House from the corner of the lawn.
The rear of Chartwell House

It’s easy to see why Winston Churchill and his wife Clementine fell in love with Chartwell House. The picturesque views across the Wealden countryside are glorious.

I loved visiting Chartwell; it is such a gorgeous home. The National Trust does a remarkable job of maintaining the impressive house, art studio, and vibrant gardens. Each garden area is so distinctive from the hidden ponds, an exquisite walled garden built by Winston, the Marlborough Pavilion, the orchards, and the lake.

Even though Chartwell is a manor house, it feels like a family home, full of precious items and thoughtful, personal touches. It even has its own resident marmalade-coloured cat.

A selection of canvases, painted by Sir Winston Churchill, in his studio in the grounds of Chartwell.
Inside Churchill’s studio at Chartwell
I must admit my favourite part of Chartwell was Churchill’s isolated art studio. It was extremely emotive and an incredible place to escape and express your thoughts and feelings to canvass.

We have created a little YouTube video of  Chartwell if you are interested.  Why not take a look?

Our final stop is 2 miles north of the historic and delightful town of Westerham.

Escape for a few days

Are you looking for that ‘perfick’ holiday hideaway to relax in while you discover the Garden of England?

After a day exploring the Kent coast and its many historic castles enjoy one of the handpicked properties and unique retreats at Holiday Cottages.

We really enjoyed visiting the market town Westerham it was full of charm and so much character. Westerham was mentioned in the Domesday Book of 1086, although it is recorded as early as the 9th-century.

Parking is available at the Darent Car Park in the east of the town.

A statue to General James Wolfe in the quaint, shops lined, Westerham Green in Kent
A statue to General James Wolfe in Westerham

Westerham not only has the political history of Sir Winston Churchill coursing through its streets, with a statue of the British statesman sitting high on the town green. But Westerham also has a famous military son, General James Wolfe, born in the town in 1727. A statue of this young Major General stands nearby Winston.

General James Wolfe was the victor of the Battle of Quebec in 1759 and where he lost his life. His childhood home Quebec House has been preserved by the National Trust and can be visited in Westerham.

The Rendezvous Brasserie on Market Square in Westerham in Kent
Rendezvous Brasserie in Westerham

Market Square has many historical and quirky buildings. Beautiful timber-framed dwellings and elegant Georgian homes. There are plenty of independent and unique shops in Westerham and some fine pubs and restaurants too.

From Westerham, drive east along the A25, passing through the quaint village of Brasted, and you’ll arrive back at Sundridge, where your road trip started. You’re now just a short hop away from the M25.

Have a delightful time on your Westerham loop road trip, and don’t forget to leave a comment below to let us know how you enjoyed your adventures.

Where to stay in Westerham

- Willow Cottage - This beautiful holiday home with exposed beams is in the heart of Westerham and surrounded by some delightful restaurants and shops. It’s around 1.7 miles from Chartwell and offers free parking.
- The Kings Arms Hotel - This charming pub is in the centre of the historic town of Westerham. It has plenty of amenities on your doorstep and offers a full English breakfast. It’s around 1.7 miles from Chartwell and offers free parking.

Our videos of the Westerham and the Weald of Kent Road Trip

We have also created a two-part YouTube video of this road trip for you to follow.  Why not check them out?
Also, why not subscribe to our YouTube channel and get the latest clips as we post them?

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