A road trip around the Kent countryside

In Counties, Kent, Our Journeys, Road Trips, Trip-Types, UK Travel by Janis10 Comments

The ‘Perfick’ way to fall in love with the Garden of England

Imagine it now, the breeze in your hair, steam engines chugging through the lush countryside, oast houses nestled by vineyards and haunted villages ready to welcome you in.

An idyllic country scene of a period house in the village of Smarden Kent

Water Lane, Smarden

Yes, you’ve arrived into “Darling Buds of May” country, in the beautiful Kent countryside in the southeast of England.
So, climb on board the “sharra-bang” (charabanc) we’re taking you on a tour of some of Kent’s most charming towns and villages.

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A pretty Tudor half-timbered house alongside two white topped oast houses in Rolvenden, Kent

Oast Houses in Rolvenden

An interesting read

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.

A little history

In this region of Kent during the 14th century, King Edward III introduced weavers from Flanders. The Wealden cloth industry then began to flourish, which resulted in so many eye-catching half-timbered ‘Cloth Halls’ dotted around the county.

We start our mini road trip adventure in Headcorn, which is only 10 miles south of Kent’s county town, Maidstone.

Looking across the High Street to ‘The Chequers’ and Shakespeare's house, behind the village War Memorial

‘The Chequers’ & Shakespeare House - cloth hall, Headcorn

When strolling around this lovely bustling village, you really feel that it has its community at heart and blends effortlessly with its historical past.

Half-timbered cloth halls are standing shoulder to shoulder in the High Street. Family-run independent stores and the traditional butchers and bakers, serving the same loyal locals for years.

Looking over the headstones of the graveyard towards St Peter and Paul's church in Headcorn

Church of Saint Peter & Paul, Headcorn

Take a stroll around the picturesque churchyard of St Peter and Paul, located at the far end of the High Street. Where there are beautiful cottages and charming medieval homes all along Church Walk.

The round trip

Although there are 10 destinations on this circular road trip, the distance from Headcorn picking up all these picturesque locations and back is only around 38 miles (62 km).

However, you may want to detour off along the way.

The next stop is Pluckley, and I love this pretty tiny village, it just feels like you have stepped back in time. If it wasn’t for a couple of modern-day vehicles, you might believe that you had strolled onto a movie set, and quite literally.

It’s here within the tranquil village of Pluckley that the heart-warming TV series “Darling Buds of May” was filmed. With the stars David Jason and Catherine Zeta-Jones, yes, it is ‘Perfick’.

A traditional butchers and post office in the village of Pluckley, Kent on a beautiful day under blue skies.

Pluckley local post office and butchers

One of the other reasons that Pluckley attracts visitors is because of its ghoulish goings-on. Pluckley is believed to be the most haunted village in England. I’ve never witnessed any spooky activities, although I wasn’t going to hang around to find out.

Gravel path leading from the church between 2 sets of cottages with one draped in wisteria on a beautiful summer’s day.

Pluckley, could it be England’s most haunted village?

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.

When we hopped out of the car at Smarden, it was one of those places that I immediately felt an affinity with. I could so comfortably live there; it was picturesque and quaint with its lovely local cricket green and half-timbered cloth halls.

A beautiful black and white half-timbered period building with a red tiled roof.  It is now home to the Chequers Inn on the High Street in Smarden Kent

The Chequers Inn on The Street, Smarden

However, it felt like the heart of the village was its community, and it was so peaceful. Very few visitors around and a couple of very tempting country pubs, serving local food and ales.

A half-timbered home, probably dating from the Tudor period, on the outskirts of the village of Smarden, Kent

Half-timbered home in Smarden

The attractive church in Smarden is St Michael the Archangel. The church is sometimes known as "The Barn of Kent" due to its high scissor beam roof. Within the church, a copy of the Royal Charter can be found. This was originally granted in 1333 by King Edward III, for the village’s efforts for the weaving industry. It was later ratified by Queen Elizabeth I in 1576.

A view from the pathway in the churchyard of St Michael the Archangel looking towards white weather boarded buildings with red tiled roofs in Smarden, Kent

Churchyard of St Michael the Archangel, Smarden

Theirs is so much history in Smarden for such a little village.

Curious to know more?

Take a look our posts on Tenterden, Headcorn and Cranbrook and find out a little more about these historical locations.

Travelling further through the Kent countryside we stop at High Halden, and park by its central village green.

An iron beacon on the village green of High Halden in front of the Chequers Inn.

Village green in High Halden

In High Halden, you must pop into the Grade 1 listed St Mary's Church. This incredible church was built during the mid-13th-century. Its unique feature is the timbered tower which was constructed in the late 13th Century. It has an octagonal ground floor, a square upper storey and then rises to an 80-foot octagonal spire.

A pathway leading to the historic Church of Saint Mary's with its timbered tower in the village of High Halden, Kent

Grade 1 listed St Mary's Church

Inside the entrance of the historic Church of Saint Mary's in the village of High Halden, Kent

Inside St Mary’s Church in High Halden

When you enter through the main wooden doors, you immediately step into a dark timber cladded area which is used by the local bell-ringers. It feels quite eerie.

Map out your route

Whether you’re planning a road trip, plotting a hiking route or cycling one of UK’s scenic trails, there’s nothing quite like using a tactile paper map.

The Ordnance Survey folk are here to help, with maps, guides, gadgets and more. Take a browse through their vast array of maps and grab your ideal companion for your adventure.

The bustling town of Tenterden has a larger community than some of the other places we visited; however, it is equally as charming.
All through the main High Street are antique shops, boutiques, coffee shops and beautiful character buildings. It is also in this delightful town that you’ll discover the nostalgic Kent and East Sussex Railway.

A selection of antique shops and tea houses line the old High Street in period buildings.  Tables and chairs line the streets while antiques and bric-a-brac fill the windows.

Quaint little stores

This heritage steam railway is kept running by enthusiasts and lovers of all things locomotive. Hop on board, and you can visit the 14th-century moated Bodiam Castle, run by The National Trust.  Which is just five stops along the line.

The back of a steam train with dark smoke coming from its chimney and the driver preparing to get on his way on a bright sunny day

Final preparations at Tenterden Town railway station

However, if you fancy a visit to a lush English vineyard, head to Chapel Down, just on the outskirts of Tenterden, the wines are incredible.

If you’re curious about English wines

Take a look at our post on our tour and tasting at Chapel Down. You can read all about our personal experience on one of their guided tours. It was so informative and relaxed, and I loved the fact they didn’t pressure you into purchasing their products.

Ahh, Rolvenden, another pretty village and this quaint little place also has a tiny motor museum, which appears to double as an antique shop.

The Rolvenden motor museum also incorporating a gift shop alongside the village antique shop.   This bijoux little museum is something to do on your Kentish road trip.

Rolvenden Motor museum

A tiny traditional petrol station in garage in the village of Rolvenden, Kent

Cornex Garage, Rolvenden

You will really want to jump out of your car here and go and discover. Not only does Rolvenden have a beautiful half-timbered cloth hall and white weather-boarded homes. It also has pretty oast houses, which are so synonymous with the Kent countryside.

A typical Tudor era cloth hall half-timbered house alongside another symbol of Kent, the white topped oast houses in the village of Rolvenden, Kent

Cloth hall & oast houses, Rolvenden

The Bull Inn, a traditional Kentish country pub with the picket fence and tables and chairs in its garden in Rolvenden, Kent

The Bull Inn, Rolvenden

Along with the antiques barn, which is overflowing with curiosities, the Bull Inn looks very tempting. Just a short walk out of the main village is the restored Rolvenden post mill, circa1580 and of a type now rare in Kent, the mill, stands on a little hill and was featured in the Tommy Steele film Half a Sixpence.

The Rolvenden Windmill and a country house just by the roadside as you leave the village.

Rolvenden windmill

The central village green and cricket ground in Benenden is so quintessentially English, with the local village church of St. George standing so proud as the backdrop.

The village sign for Beneden in Kent depicting a man playing cricket whilst wearing a top hat

Benenden village sign

Never one to pass up an opportunity to take a stroll around an ancient churchyard. Gary and I had a little wander and found some touching Commonwealth war graves.
Benenden has a lovely village feel with quaint, picturesque homes surrounding the green. One of which was an old converted school. Then a short walk further on and there are tea rooms and little stores vying for your custom.

A historic home that was once the old school in Beneden , Kent

Old School in Beneden

Tempted to?

Discover more of the Great British Isles, why not jump in a car and tour the country at your own pace. You can do it all on a road trip, Rental Cars cover all budgets and allow you to pick up and drop off at different destinations.

Heading onto Cranbrook, which is a small town, is in the heart of Kent’s ‘High Weald’. The countryside all around this area of the High Weald is beautiful, so it’s no surprise that it has been classified as ‘AONB’ Area of Outstanding Natural Beauty.

The White Horse public house takes pride of place in the High Street of Cranbrook.  The windows are decorated with brightly coloured hanging baskets.

White Horse pub, Cranbrook

Cranbrook has some really attractive features, black and white half-timbered homes, beautiful English country gardens and a very interesting local church.

Within the church’s tower is a clock mechanism, which was installed in 1855 and was the prototype for ‘Big Ben’ in London.

A view over the graveyard towards the apex end the Saint Dunstan's church in Cranbrook on a beautiful sunny day

St Dunstan's churchyard, Cranbrook

Just a short hop from the church is the late medieval George Hotel, which has undoubtedly had a chequered past. As it was once frequented by Queen Elizabeth, I in 1573 and then during the 18th-century smugglers from the notorious Hawkhurst Gang hatched plans from here.

Just a short hop north from Cranbrook and you’ll arrive at Sissinghurst. Although this village is tiny, it’s so pleasant to visit.

Quaint little homes with white picket fences around their front gardens, overflowing with rambling roses and colourful window boxes.
Even though the village is small, there is always a place for the local store, as this is so often the hub of a community.

Looking along the High Street of Sissinghurst in Kent past beautifully decorated red brick homes

Sissinghurst High Street

Last but by no means least is the larger village of Biddenden. This village also has strong links with the Flemish clothworkers, as you’ll see there are quite a few half-timbered cloth halls dotted all around.

The town sign for Biddenden featuring the two ‘Biddenden Maids’ on a triangle section separating the road in front of traditional red brick homes.

Biddenden with the ‘Biddenden Maids’ village sign

This is once again lovely village to take your time to stroll around as it is immaculately kept and has an attractive 13th-century church. You can also pop into one of the local tea rooms and enjoy a cream tea while watching the world go by.

Half-timbered buildings on the corner of the High Street of Biddenden, Kent on a beautiful summers day

Biddenden High Street

Biddenden is also known for its ‘Biddenden Maids’ who were conjoined twins born in 1100. Eliza and Mary Chulkhurst were joined at the shoulder, and the hip and amazingly lived to the age of 34 years. The village sign in Biddenden is a touching depiction to them.

Other villages to discover

You can now head back to Headcorn, or if you have a few days to discover more of the beautiful county of Kent. Why not also take a peek at Appledore, Charing and the Market town of Lenham?

Would you like a little more?

We have created a little YouTube video of road trip - why not check it out?

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

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Inspired to tour Kent on a road trip?

Enjoy an overnight stay in one of Tenterden’s local inns spend a full day discovering the town and surrounding countryside.

The open roads await, pop in your location details then Rental Cars will search well-known car hire brands and discover the deals that suit you the best.
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About the Author


Janis, the co-founder of Our World for You, was born in London and raised in Kent and the Isle of Wight. Along with Gary her partner, they have been travelling part time since 1995. In 2016, they decided that enough was enough with the 9 to 5, so armed with the knowledge and experience that they had gained on their adventures, that they wanted to inspire others to travel the world near and far.

Trips100 - Travel Blogs
Trips100 - Travel Blogs


    1. Author

      Ahh, thank you very much, that must have been a lovely experience. There is still such a warming village feel in a lot of these places, glad it brought make some lovely memories.

  1. You’re really inspiring me to travel more around Kent. We live further west and I think it would be a super idea to visit a few of these lovely towns and villages on a road trip. Thanks for sharing this on #farawayfiles

    1. Author

      There really are some pretty villages in Kent and the countryside is beautiful too. It would certainly make a great day trip for you, hopping from one to another.

    1. Author

      I must admit it amazed me just how many half-timbered houses there were. I believe a lot of them originated from when the Flemish cloth workers were in the county.

  2. We’ve visited Kent each February for the last couple of years and I still feel like we’ve barely scraped the surface. I’d love to explore more of these towns. #FarawayFiles

    1. Author

      I know what you mean there are so many pretty villages throughout the county. Hopefully there are some places in this post, that you haven’t visited yet and then you’ll just have to return.

    1. Author

      It is a lovely part of the country and with so much history. I agree with you, the White Horse pub does look very tempting.

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