Westerham, Kent:  A Guide To Churchill’s Hometown

Westerham at a glance:

• Travel time: 45mins drive from London, or a 30min train to Sevenoaks followed by a short bus ride.
• Vibe: Traditional, charming, historic.
• Top must-see: Chartwell – the beloved family home and gardens of Sir Winston Churchill.
• Best for: History buffs, beer lovers (the local brewery is famous!), walkers.

This guide has everything you need to enjoy a trip to Westerham, Kent. It’s a pretty town, known by many as being the hometown of former Prime Minister, Winston Churchill, for over 40 years. It’s also a great spot for independent shopping and dining out. Being close to the countryside too and on the border of Surrey, it’s near many great places for those that love spending time outside.

Places to eat in Westerham

No trip is complete without good food, which is why I have included places to eat in Westerham, Kent first. Although the town is fairly small, there’s no shortage of options to eat out, no matter the time of day.

Chows

This Chinese restaurant has been in Westerham for 25+ years. When I dined there the food was great and the service quick, even with a large table of us dining and lots of different dishes to prepare. There was a good atmosphere from other customers being around. Mr Chow is very friendly and attentive too, speaking to all the guests that dine there.

Rendezvous Brasserie

Another restaurant that has survived the test of time is Rendezvous, which opened over 30 years ago in Westerham. They serve classic French cuisine, in a simple, modern setting. This spot is also open for breakfast which is great for people staying in the area – the menu is full of eggs though, so not somewhere to head if you’re a vegan.

The Old Bank

If you’re one for fine dining, The Old Bank is the place to head in Westerham. The head chef Adam has trained with some of the best, including the head chef for the Queen. The regal deep green exterior is matched by elegant interiors and expertly plated food. The former vault is now a wine cellar which you can visit for wine tasting sessions.

Tudor Rose Tea Rooms

Located in a central spot behind the Winston Churchill statue on the green is the Tudor Rose. There have been tea rooms in this spot for over 100 years! The menu is made up of everything you’d want from a tea room – tea, cake, sandwiches, and even full English breakfasts. If you’re lucky, you may be able to nab a spot to dine outside on a sunny day.

Grasshopper on the Green

With low ceilings, antique jugs and a roaring fire, the Grasshopper on the Green is a 700 year old pub with an oldy worldy charm about it. The twinkling fairy lights outside welcome you in. There’s also a small garden for drinks in the summer, as well as picnic tables on the green. The menu is full of hearty meals including pies, burgers, chilli, and roast dinners.

No17 Wine Bar

You’re spoilt for drinks choice at this bar with a 15 page menu full of wines, gins, and cocktails. The interior is stylish and contemporary, offering something different to this historic town. Nibbles are available too, and there is regularly live music.

Napoli e

Tucked away down a side lane is this Italian restaurant. You could almost be fooled into thinking you had stepped out of Westerham, Kent and into Italy with its authentic feel. The menu is full of the classics you’d expect, with a wide range of pastas and pizzas as well as meat and fish dishes. Food is cooked to order using fresh ingredients and online reviews all rave about the ambiance.

Shopping in Westerham, Kent

Shopping in Westerham, Kent is a must if you visit, as there’s several independent shops and boutiques. Whether you’re looking to pick something up for yourself or treat a relative or friend, you can find homewares, fashion, food and more here.

The Interior Design Studios

If you’re looking for statement pieces for your home, then you need to look in this interior design store. From the outside it’s a very attractive building but you can’t tell just how far back the shop stretches, and there’s a downstairs too. I saw some of the biggest chandeliers I’ve ever seen in here! There’s plenty of unique pieces of furniture that will be the talking point for any visitors to your home.

Chocs on the Green

This sweet little shop is full of greetings cards, gifts, chocolate, and fudge – everything you need to celebrate an occasion in one shop. You can buy pre-made chocolate boxes, or pick chocolates individually to make up a personalised box. There’s a lot of variety, and the options change seasonally too. I was impressed that they had a range of vegan options as I can’t have dairy so I enjoyed some fudge from here.

Quercus Wines

This small but perfectly formed shop is the place to head if you’re a wine fan. There’s a range of wines to browse, that have come from small wine producers around the world. The selection is regularly changing, and the owner can help advise if you’re not sure what to pick.

The Vintage Home Co

This home interiors shop has been based in one of Westerham’s Victorian buildings for over 16 years. It’s a maze of different rooms and an outdoor space filled with furniture and homeware that’s been carefully curated. It’s a lovely shop to explore and is definitely loved amongst locals who like to check out the latest finds in the window display.

Places of interest in Westerham, Kent

As well as shopping and dining on the main high street, there’s plenty of other places to explore in and around Westerham, Kent. You can try out locally produced beers and wines, enjoy the history of National Trust owned properties, or get some fresh air with plenty of walking routes.

Chartwell

The home to former Prime Minister Sir Winston Churchill, this property is now owned by the National Trust. It sits in beautifully maintained gardens and there is also a restaurant and shop on site. The rooms in the house remain much as they were when he lived there, and you can also see many of the paintings Churchill completed.

Westerham Brewery

Westerham has a strong background in producing beer. Not only are there tours of this brewery, there’s also street food traders who serve meals here on different nights of the week. This includes spaghetti on Wednesdays, pizza on Fridays, fried chicken and hotdogs on Saturdays, and Italian seafood on Sundays.  

Quebec House

This is another National Trust owned home which was once the residence of James Wolfe, a British army general who was born in Westerham. Under his command the British won against the French in the Battle of Quebec, however sadly James was fatally wounded. You can discover more about his life and his childhood at this property.

Toys Hill

Yet another area owned by the National Trust, Toys Hill is made up of more than 200 acres of woodland. It offers great views over the Weald of Kent, and is a great picnic spot. It’s recognised as a grade I site for nature conservation. If it’s a sunny day and you’re driving, aim to get there early as the car park and the road leading to it quickly fills up.

Squerryes Winery

Squerryes is a 300 year old estate where you can tour the vineyards and of course, enjoy wine tasting sessions in their special tasting room. You can discover more about their ancestral estate and vintage sparkling wines. If you want to eat, there’s a restaurant on site too.

Limpsfield Chart

This is a lovely trail to walk in the woodlands. Even better, it has a hidden fairytale animal village called the Peter Rabbit Trail. It’s rather enjoyable to spot the different animal lodgings if you’re out on a dog walk or visiting with children! There’s a few different car parks in the area but the closest to the Peter Rabbit Trail is Ridlands Grove.

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