In partnership with Visit Tunbridge Wells | High Weald Walking Festival 2025
Free guided walk with Boots on Adventures - 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, the “Capital of the Weald.” From the High Street, we’ll venture across rolling fields and ghost traces of Roman roads, winding through one of England’s most treasured historic landscapes.
We'll arrive near the iconic Sissinghurst Castle Garden, once home to writer Vita Sackville-West. While we won’t be entering the main National Trust property, public footpaths offer striking views of the famous tower and glimpses into the estate’s remarkable past.
Throughout the walk, your guide Ben Crozier will share tales that bring the Wealden countryside to life — from ghost stories and wartime memories to the bohemian history of Sissinghurst.
⭐ Highlights
🥾 7.4-mile circular walk through the High Weald National Landscape
🏰 Views of Sissinghurst Castle Garden from nearby countryside
📜 Local legends & historic tales from your Boots on Adventures guide
🌳 Woodlands, farmland & Roman routes in one stunning walk
📅 The Details
🗓 Date: Sunday, 21 September 2025
🕤 Meet Time: 09:15 for 09:30 start
🚶♂️ Duration: Approx. 4.5 hours (incl. lunch break)
👣 Walk Leader: Ben Crozier
📌 Meeting Point:
The High Street Car Park, High Street, Cranbrook, TN17 3DW
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🚗 Parking: Available but charges apply (not included)
🗺 Route Info
📏 Distance: 12.05 km / 7.4 miles
🔄 Type: Circular
🌾 Terrain: Largely flat with a few stiles
🐕 Dogs: Friendly dogs welcome, must be on a lead
🎒 Kit List
👟 Walking boots or sturdy footwear (no flip-flops)
🌧 Waterproof coat (and trousers if you have them)
🥪 Packed lunch & drinking water
💊 Any personal medication
👕 Comfortable walking attire
⚠️ Important Notes
📸 Photos may be taken for promotional/training use – let us know if you prefer not to appear.
🐾 Dog owners are fully responsible for their pets throughout the walk.
✅ Booking essential – limited spaces available due to group size restrictions.
🔁 Can’t make it? Please let us know as soon as possible so we can offer your space to someone else.
🧭 Whether you're local or discovering the Weald for the first time, this walk blends heritage, nature, and storytelling into one unforgettable experience.
You may also like the following events from Boots On Adventures:
- This Sunday, 20th July, 09:30 am, A historical walk from Cobham to Luddesdown in Gravesend
- Next Friday, 25th July, 05:00 pm, Woodland Club - Fire, Food & Forest Celebration in Faversham
- Next Sunday, 27th July, 09:30 am, Higham Loop via Shorne Marshes in Rochester
Also check out other
Festivals in Cranbrook,
Trips & Adventurous Activities in Cranbrook.
