A historical walk from Cranbrook to Sissinghurst (Booking Essential)

BOOKING ESSENTIAL

Boots on Adventures is excited to team up with Visit Tunbridge Wells for this year’s High Weald Walking Festival, offering a unique free guided walk that celebrates the rich history and natural beauty of the High Weald National Landscape.
Our journey begins in Cranbrook, a charming market town known as the “Capital of the Weald.” From the High Street, we’ll venture out across rolling fields and along the ghost traces of ancient Roman roads, winding through the heart of one of England’s most treasured historic landscapes.
The route leads us to the iconic Sissinghurst Castle Garden, once home to the writer Vita Sackville-West. While we won’t enter the main National Trust property, the surrounding public footpaths provide striking views of the famous tower and glimpses into the estate’s fascinating past.
Throughout the walk, you’ll hear captivating stories that bring the countryside to life — from ghostly legends and evacuees to grumpy WWII prisoners of war and bohemian parties that left their mark on this peaceful corner of Kent.
Highlights:

• A 7.4-mile circular walk through the High Weald National Landscape
• Views of the iconic Sissinghurst Castle from the surrounding countryside
• Historic tales and local legends shared by your Boots on Adventures guide
• A friendly group walk through woodlands, farmland, and historic routes.

Whether you’re a local explorer or visiting the Weald for the first time, this walk offers the perfect mix of heritage, landscape, and storytelling.
the details
Schedule
Date: 21 September 2025
Meet and Start Time: 09:15 meet for 09:30 am start
Walking time: 4.5 hrs (incl. lunch break)
Staff Member: Ben Crozier
Location
Meeting point:
High Street Car Park, Cranbrook, TN17 3DW
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Car Parking: Charges not included
Route
Terrain: Largely flat with a few styles.
Distance: Approximately 12.05 km (7.4 miles)
Walk Type: Circular
your kit list

• Suitable footwear (preferably walking boots or sturdy shoes, no flip-flops)
• A waterproof coat (and waterproof trousers, if you have them) for rainy days
• Drinking water and a packed lunch
• Personal medication (Let us know confidentially about any medical conditions)
• Suitable walking attire

important notes

• We welcome friendly dogs on our walks, provided they remain on a lead at all times. The owner is fully responsible for their dog throughout the walk.
• We take photos during our walks for promotional and training purposes. If you prefer not to be included, just let us know on the day.
• Cancellation policy states: Can’t make it? Please let us know as soon as possible so we can offer your space to someone else.