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.
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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Discover Emmetts GardenA 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.
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.
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.
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.
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.
Where to stay in Hever
Our Kent road trips
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.
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.
Inspired into creating your own adventure?The planning starts here
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.
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.
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.
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.
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
Our videos of the Westerham and the Weald of Kent Road Trip
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