Boots on Adventures is excited to team up with Visit Tunbridge Wells for this year’s High Weald Walking Festival.
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 what3words: ///unit.snippets.secure 🚗 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.Hotels near The High Street
Staying overnight in Cranbrook?
Wondering where to stay that's close to The High Street? We've teamed up with Booking.com to provide the best room rates for hotels, guesthouses and B&Bs near the A Historical Walk From Cranbrook To Sissinghurst event in Cranbrook.
The George Hotel &
In a historic 14th-century building, this beautiful boutique hotel houses 12 unique and individually designed rooms, offering a stunning blend of stylish contemporary design and beautiful original period features..
The Old Telephone Exchange
Situated in Sissinghurst, this holiday home features a barbecue. It provides free private parking. Canterbury is 41 km from The Old Telephone Exchange, while Eastbourne is 42 km away.
The Goudhurst Inn
Featuring free WiFi, a restaurant and a terrace, The Goudhurst Inn offers accommodation in Goudhurst. Guests can enjoy the on-site restaurant. Free private parking is available on site.
The Star And Eagle
Once an ancient monastery, The Star and Eagle Hotel dates back to the 14th century. It offers charming accommodation in the Kent countryside, 20 minutes drive from Royal Tunbridge Wells..
Southgate - Little Fowlers
Situated in the quiet village of Hawkhurst, 6 miles from Sissinghurst and a 25-minute drive from Royal Tunbridge Wells, the 300 year old country house Southgate - Little Fowlers boasts 5-star accommodation, beautifully landscaped gardens, free Wi-Fi,...
Field Green Oast
Nestled 7 miles south of the historic market town of Cranbrook, Field Green Oast is a converted square kiln oast house with free WiFi and free on-site parking..
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VenueThe High Street
AddressThe Street, Cranbrook, Kent,
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