Skip to content
A statue of Winston and Clementine Churchill in the grounds at Chartwell
A statue of Winston and Clementine Churchill in the grounds at Chartwell | © National Trust Images/Sarah Haile
Kent

Westerham to Chartwell trail

Enjoy a countryside walk through the Weald of Kent, starting in the village of Westerham and finishing at Chartwell, Winston Churchill's family home.

Road safety

You will cross busy roads at several points on this trail route. Please exercise caution when crossing and watch out for oncoming traffic.

Total steps: 14

Total steps: 14

Start point

Winston Churchill bronze statue on The Green, grid ref: TQ447540

Step 1

Start at the bronze statue of Winston Churchill on the green in Westerham. Walk towards the bus stop and cross the A25 at the crossing in front of the bus stop. Having crossed the A25 you will see an alleyway in front of you to Water Lane. Continue up the alleyway. After a short way you will come across a small stone hump; take care when stepping over this.

Step 2

At the end of the alleyway you will come to a wooden kissing gate. Continue through the gate, entering the field (please keep dogs on lead at all times in the field) and head up the slope. Continuing up the slope, you will see a waymarked post pointing towards a metal kissing gate at the brow of the slope. Continue to the gate.

Step 3

Go through the metal kissing gate into the next field and continue on straight ahead. You will come to a crossroad and meet a waymark. Continue on straight ahead.

Step 4

You will meet another waymark prior to a steep slope. Follow the arrow and carefully descend the slope, taking care in wetter conditions. Head for the metal kissing gate in the corner of the field which will come into view as you descend.

Step 5

Go through the kissing gate, entering a pine woodland. You will see a waymark pointing straight ahead; follow this path. You will come to a junction with a path going off to the left and the main path climbing up in front of you, which you will need to follow.

Step 6

At the next waymark post, take a left turn. Continue up the path for approximately five minutes. You will reach Hosey Hill Road and a waymark.

Step 7

The waymark points across Hosey Hill Road at an angle. We recommended that you walk along the grass verge for 50 metres and cross parallel with the waymark on the opposite side of the road. Take care when crossing as the road gets very busy.

Step 8

Once in the car park you will see a waymark pointing to the right, out of the car park and up the path on the left-hand side. Shortly after you will see another waymark confirming the direction upwards. Follow the path and you will join a main path and meet a waymark pointing leftwards.

Step 9

Follow this path climbing gently upwards and continue until you see a slight clearing on the right. You will see a waymark indicating the direction to follow.

Step 10

Continue along the path until you reach a Y-junction and follow the direction on the waymark. As you walk this stretch of path it will begin to narrow and change shape. You will meet a crossroad and another waymark pointing ahead.

Step 11

Follow the path up ahead and you will come to a T-junction and a waymark pointing right. Take this turn.

Step 12

At the end of this path you will see a vehicle barrier and a waymark pointing across Hosey Lane. On the other side of the road you will see a Y-junction with a footpath to the right and another to the left. Follow the left path.

Step 13

Continuing downwards on this path you will notice a slight clearing to the right and a waymark on the fencing to the left. Continue in the waymarked direction.

Step 14

You will arrive at Mapleton Road with the Chartwell car park entrance on your left.

End point

Chartwell, grid ref: TQ454513

Trail map

Westerham to Chartwell, Kent trail map
Westerham to Chartwell, Kent | © Crown copyright and database rights 2013 Ordnance Survey

You made it

Share your experience

More near here

Rear view of Weardale Monument at Toys Hill, Kent. Tree trunk and roots in foreground
Trail
Trail

Weardale circular walk from Chartwell 

A beautiful 3-hour walk that links Chartwell with Emmetts Garden. From daffodils and bluebells to roses and autumnal shades, enjoy a rainbow of colour throughout each month of the year as you walk through the West Kent countryside.

Activities
Walking
DistanceMiles: 5 (km: 8)
A summer view across the Weald of Kent from Mariners Hill, a National Trust countryside site in Kent
Trail
Trail

Mariners Hill from Chartwell walk 

Explore Mariners Hill and enjoy views of Winston Churchill's home at Chartwell and the Weald in Kent on this moderate circular walk.

Activities
Walking
DistanceMiles: 1.4 (km: 2.24)
A summer view across Chartwell house and beyond from Mariners Hill
Trail
Trail

Hosey Common to Mariners Hill loop walk 

Explore Mariners Hill on this circular trail, which takes in fantastic views over Sir Winston Churchill's home at the Chartwell estate and the Weald of Kent.

Activities
Walking
DistanceMiles: 4 (km: 6.4)
Rear view of Weardale Monument at Toys Hill, Kent. Tree trunk and roots in foreground
Trail
Trail

Weardale circular walk from Chartwell 

A beautiful 3-hour walk that links Chartwell with Emmetts Garden. From daffodils and bluebells to roses and autumnal shades, enjoy a rainbow of colour throughout each month of the year as you walk through the West Kent countryside.

Activities
Walking
DistanceMiles: 5 (km: 8)

Get in touch

Mapleton Road, Westerham, Kent, TN16 1PS

Our partners

Cotswold Outdoor

We’ve partnered with Cotswold Outdoor to help everyone make the most of their time outdoors in the places we care for.

Visit website 

You might also be interested in

A hiker wearing an insulated jacket and a backpack watches the sunset over snowy mountain peaks

Walking 

Explore some of the finest landscapes in our care on coastal paths, accessible trails, woodland walks and everything in between. Find the best places to walk near you.

A view of the lake and garden with the house in the distance in spring at Chartwell, Kent
Article
Article

The estate at Chartwell 

Chartwell’s estate and surrounding countryside offers far-reaching views across the Weald. Walk in the footsteps of one of our founders Octavia Hill when you explore Mariners Hill.

A close up of a scone covered in cream and jam
Article
Article

Eating and shopping at Chartwell 

From tasty treats and hot and cold dishes, to souvenirs, gifts and Churchill memorabilia, you'll be spoiled for choice in the Chartwell café and shop. Why not treat yourself?

An aerial view of an adult and baby walking a dog along a path at Baggy Point, Devon
Article
Article

Staying safe at National Trust places 

The special places in National Trust care sometimes come with a few risks for visitors, be it coastline or countryside. Find out how to keep safe throughout your visits.

A visitor carrying a backpack and walking along a footpath at Divis and the Black Mountain with stone walls either side, the countryside visible in the background.
Article
Article

Follow the Countryside Code 

Help to look after National Trust places by observing a few simple guidelines during your visit and following the Countryside Code.

A group of people in a hiking group are being guided on a hike by rangers at Marsden Moor, West Yorkshire
Article
Article

Cotswold Outdoor: our exclusive walking partner 

Find out more about the National Trust’s ongoing partnership with Cotswold Outdoor as our exclusive walking partner.