There’s something special about a crisp autumn morning when you pack the dogs in the car, and head off somewhere to find some peace and spot some beautiful autumnal colours. Recently, I did just that and decided to visit the wonderful grounds of Chartwell, Sir Winston Churchill’s much-loved country home just over the border from Surrey into Kent.

Chartwell is situated in Westerham, which is actually a cute little town with charming shops and restaurants and worth a visit too. When I first drove through here it reminded me a little of Reigate, but with a nicer, gentler feel and just a little bit more refined.

Whether you’re drawn by the history, the scenery, or the promise of a peaceful walk with your four-legged friend, Chartwell is one of those places that feels both grand and welcoming. It’s a little slice of English countryside calm with a fascinating story woven through it.

A warm welcome (and free parking for National Trust members!)

Driving in from Surrey, the journey to Chartwell, Westerham is perfect for getting that countryside vibe before you even get there. You’ll experience winding lanes, rolling hills and those postcard-perfect views Kent is known for. There’s an ample car park with space for an overflow if necessary, and if you’re a National Trust member, it’s free (always a win in my book.)

From the moment I stepped out of the car, I could sense why Churchill fell in love with this place. His quote about the view being “the most beautiful and charming I have ever seen” couldn’t be more true.

Friendly staff will greet you at the admissions desk and if you need a map or the kids want a trail to follow, you can get one here.

Don’t forget to get your dogs’ PAWSport stamped here too!

Exploring the gardens with the dogs

Dogs are welcome at Chartwell, though they do need to stay on leads. My two were in their element, tails wagging as we followed the paths that wind through the estate. My older dog, who’s now twelve and can’t manage long walks anymore, still enjoyed a gentle meander around the formal gardens, stopping to sniff the autumn air and the scent of other dogs.

The paths are well-kept, and there are plenty of benches where you can pause and soak in the views across the Weald of Kent. For more energetic pups (and humans) there are longer woodland trails that weave through the surrounding countryside. There’s a woodland walk within the grounds, which takes you around the outskirts. It’s a little hilly but worth the walk and you’ll discover a bomb crater if you make it to the top of the hill.

If you’re planning a dog-friendly walk near the Surrey/Kent border, Chartwell is perfect, just enough space to stretch your legs without feeling rushed, and plenty of peaceful corners to sit and take in the scenery.

Don’t miss…

I don’t want to spoil it all by over sharing but there’s so much to see at Chartwell. You’ll get to see the outdoor swimming pool, built by Churchill and often enjoyed by the black swans that live on the estate. There’s also a fish pond with a perfectly situated chair where Churchill liked to sit. The walled gardens are a delight and this time of year filled with dahlias, produce and lots of pumpkins. Look carefully in the walled garden and you’ll discover the ‘Mary Cott’ a cute little brick built miniature play house that Churchill built for his youngest daughter.

One of my favourite spots is the Marlborough Pavilion, a fascinating little building, decorated with stunning murals telling the story of the Battle of Blenheim, inspired by his ancestor, the 1st Duke of Marlborough. 

The house and its history

Because I had my dogs with me, I couldn’t go inside the house this time, but it’s worth mentioning that Chartwell House is beautifully preserved, almost exactly as the Churchills left it. Inside you’ll find Churchill’s study, his art studio in a separate building, and family rooms, giving a glimpse into the private life of one of Britain’s most remarkable figures. You can also enjoy viewing loads of photos and artefacts.

If you want to see inside, timed entry tickets are available on the day from the admissions desk (it’s best to arrive early on weekends). Dogs aren’t allowed indoors, so if you’re visiting as a couple or with friends, you might take turns exploring while someone enjoys a coffee or time outdoors with the dogs.

A bite to eat or a quick coffee

After our walk, we stopped by the café for a quick sandwich, although there was plenty more available. There are picnic tables outside where dogs are welcome, making it an easy, relaxed stop after exploring the gardens. On the way out I noticed that some people were inside with their dogs. There must be a separate dog friendly area inside, which is definitely worth remembering, especially as the weather continues to cool down.

There’s something so peaceful about sitting in a scenic spot, looking across the lawns towards the hills, and thinking of Churchill painting that very same view decades ago.

What you need to know before you go

• Location: Mapleton Road, Westerham, Kent, pop TN16 1PS into your satnav or phone.
• Parking: Free for National Trust members.
• Dogs: Welcome on leads in the gardens, grounds and woodland trails, but not inside the house.
• Facilities: Dog-friendly outdoor seating at the café, water bowls available.
• There’s no need to book if you are a National Trust member.
• Take your phone or camera – there are some stunning opportunities for photos all year round.

Chartwell is one of those rare places that offers something for everyone – history, art, glorious countryside views and a genuinely dog-friendly atmosphere. Whether you’re after a peaceful National Trust dog walk, a scenic day out local to Surrey, or simply a new corner of Kent to explore, it’s well worth a visit.

As we headed home, two happy, sleepy dogs in the back of the car, I couldn’t help thinking that Churchill had it right. A day spent at Chartwell is a day well spent indeed!