Discover Churchill’s Chartwell: A Stunning Walk Around Westerham

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Tucked away in the rolling hills of Kent, the charming town of Westerham offers a perfect blend of history and natural beauty. This walk takes you through tranquil woodland, across meadows, and along scenic bridleways to Chartwell, the former home of Winston Churchill. Whether you’re a history buff, a nature lover, or just looking for a peaceful countryside escape, this 5-mile (8km) circular walk is one to add to your list.

Walk Overview

This scenic circular walk around Westerham takes you through the rolling countryside of Kent, with stunning views, historic landmarks, and peaceful woodland paths. The route is approximately 5 miles (8 km) and follows a mix of well-maintained footpaths, bridleways, and quiet country lanes. It offers a moderate challenge, with some gentle inclines and uneven terrain, making it ideal for walkers with a reasonable level of fitness.

The walk takes in key historical sites, including Chartwell, the former home of Sir Winston Churchill, and the beautiful countryside that inspired him. You’ll also pass through the picturesque village of Westerham, with its charming Georgian buildings, independent shops, and inviting pubs.

Public Transport Options

Westerham is well-connected by public transport, making it a convenient walking destination for those traveling without a car.

By Train: The nearest railway stations are Oxted and Sevenoaks.
- Oxted Station (served by Southern and Thameslink trains) is approximately 4 miles from Westerham. From here, you can take bus #594 or #595 to the town center.
- Sevenoaks Station (served by Southeastern trains) is around 7 miles away, with bus #401 running to Westerham.
By Bus: Several bus routes serve Westerham from nearby towns:
- #246 from Bromley (via Hayes and Biggin Hill)
- #401 from Sevenoaks
- #594/#595 from Oxted

Most buses stop in Westerham town center, making it an easy starting point for the walk.

Points of Interest

This walk offers a mix of history, nature, and breathtaking scenery. Highlights include:

Chartwell – The former home of Winston Churchill, now managed by the National Trust. You can explore the house, gardens, and woodland that Churchill loved so much.
Quebec House – A charming 18th-century house and the childhood home of General James Wolfe, the British officer who led the victory at the Battle of Quebec in 1759.
The Green, Westerham – A picturesque village green featuring statues of Sir Winston Churchill and General James Wolfe, celebrating their connections to the area.
Squerryes Court & Estate – A historic manor house with beautiful gardens and a vineyard, offering wine tastings and estate walks.
Valence School & Tower Woods – A lovely wooded section with scenic views over the surrounding countryside.
The North Downs Way – Part of the route follows this famous long-distance trail, offering spectacular panoramic views.

Starting the Walk: Through Westerham and Into the Countryside

Begin your journey at Westerham’s church, a picturesque spot at the heart of the town. From here, head towards the village green, where you’ll find a statue of Churchill himself. Cross the road and take Water Lane, directly opposite the statue.

As you follow Water Lane, you’ll soon reach a stone stile. Climb over and continue across the first meadow. The path takes you into a second meadow, and about halfway across, look out for a kissing gate well-hidden in the hedge—pass through here to continue your journey.

Woodland Trails and French Street

The next section leads you along a narrow lane before reaching a road. Turn right, then shortly after, look for a patch of common land on your left. Take the metalled lane that curves around a house and through the trees. Soon, you’ll arrive at a hard track—follow this by turning right, leading you towards the quaint hamlet of French Street.

Following the Greensand Way to Chartwell

As you pass April Cottage and Appletree Cottage, take the bridleway that veers slightly left. Follow this track through the woodland, eventually joining the Greensand Way. Enjoy the peaceful surroundings as you navigate through the trees, crossing a minor road before reaching a stile. Climbing over, you’ll find yourself at the entrance to Chartwell, the beloved home of Winston Churchill.

If you wish, take some time to explore the house and its beautiful gardens before continuing your walk.

Rolling Hills and Returning to Westerham

After crossing the road, continue along the Greensand Way, climbing a few stone steps before the path curves to the right. Soon, you’ll reach The Warren, an old brick house. From here, follow the tarmac track downhill until you reach a larger road. Turn right, walking alongside the road, before taking another right at the sign for Kent Hatch.

This bridleway leads past an isolated house built in 1787, then curves left towards another stile. Climb over and continue following the Greensand Way—be cautious here, as the path can be muddy at times. As you walk, enjoy the sweeping views over the Kent countryside.

Eventually, the landscape opens up. Cross a final set of stiles before the path descends into the outskirts of Westerham. Pass a small pool, then take one last stile before emerging into the village. Turn right, walk up the main street, and return to your starting point.

Why You’ll Love This Walk

This route offers something for everyone: historical intrigue, peaceful woodland trails, and stunning open landscapes. The highlight, of course, is Chartwell, a place steeped in history where Churchill spent his later years writing, painting, and tending to his garden.

For a perfect ending to your walk, why not stop at one of Westerham’s charming pubs or cafés? The Grasshopper is a historic pub dating back to the 13th century, while Tiffins and The Tudor Rose offer classic afternoon tea.

If you have time, make a detour to Squerryes Court, a beautiful 17th-century manor house visible on your return route. Though not a museum, the house holds an impressive collection of fine art and furniture.

Final Thoughts

This five-mile circular walk is a delightful way to experience the Kent countryside while stepping into the world of one of Britain’s greatest leaders. Whether you come for the history, the wildlife, or just a good excuse to stretch your legs, Churchill’s Hideaway at Westerham is a walk well worth taking.