A Historical Walk from Chilham to Perry Woods Guided History Walk
Castles, ancient woodland and hidden stories
Step back in time….
On Sunday 13th September for a guided historical walk exploring one of Kent’s most picturesque villages and the beautiful countryside that surrounds it. Starting from Taylors Hill Car Park in Chilham, this circular route leads through rolling farmland, ancient woodland, and quiet country lanes before climbing to the magnificent Perry Wood.
Leaving Chilham behind, we’ll pass the impressive Chilham Castle before making our way through fields and woodland towards the rural hamlets of Dane Street and Shottenden. From there, the route climbs steadily to Perry Wood, one of Kent’s largest and most beautiful ancient woodlands, before winding its way back to Chilham through peaceful countryside.
Throughout the walk, you’ll hear fascinating stories that bring the landscape to life, including villages that have starred in countless films and television productions, ingenious communication systems that once linked communities across the countryside, and the secret burial place of a saint. Combining stunning scenery with engaging local history, this walk offers a memorable journey through one of Kent’s most captivating landscapes.
The details about A historical walk from Chilham to Perry woods
the details
Schedule
Date: 13 September 2026
Meet and Start Time: 09:15 meet for 09:30 am start
Walking time: 4.5 hrs (incl. lunch break)
Walk Leader: Ben Crozier
Location
Meeting point: Taylors Hill, Chilham, Canterbury CT4 8BZ
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Car Parking: Charges not included
Route
Terrain: There will be a few undulating hills and one long climb in the middle of the walk.
Distance: Approximately 12 km (7.5 miles)
Walk Type: Circular
Difficulty: Moderate
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: Full payment becomes due if a user cancels within 4 days of the activity. Any person cancelling outside of 4 days, will receive a credit available to use within 90 days. Cancel at least 4 days before the event to receive a credit note for a future walk, valid for 90 days.
Learn more aboutthis wonderful walk
Explore the history, landscapes, and hidden stories of the Kent countryside on this guided circular walk led by Ben Crozier and the Boots on Adventures team. Covering approximately 13.3 kilometres (8.3 miles), this route combines scenic rural walking with fascinating storytelling, creating a memorable and engaging day out.
Starting from Bridewell Lane Car Park in Tenterden, the walk begins by gradually leaving the bustling town behind and entering the quieter countryside that surrounds it. The route passes through a varied landscape of open fields, orchards, woodland paths, and country lanes, offering a classic taste of the Kent Weald.
As we make our way towards Rolvenden and Rolvenden Layne, the scenery becomes increasingly peaceful and rural. Along certain sections of the route, there may even be the sound of steam trains travelling along the nearby heritage railway, adding another layer of character to the walk and connecting the landscape to its transport heritage.
The route also follows streams and waterways that gently weave through the countryside, bringing a calm and timeless quality to the journey. These natural features, combined with orchards and rolling farmland, create a landscape that feels deeply connected to Kent’s agricultural past.
A central part of this walk is the storytelling woven throughout the day. Along the route, Ben will share tales of unusual local events and intriguing historical figures, including a dramatic incident involving a windmill, a Reverend whose actions caused problems with royalty, and stories linked to a secret garden hidden within the area.
The walk is expected to take around four and a half hours at a relaxed and sociable pace, allowing time to enjoy the scenery and hear the stories connected to the places we pass through. The terrain is mainly flat with a few gentle hills and some stiles along the way, making it suitable for walkers with a reasonable level of fitness.
Dogs are welcome provided they are friendly and kept on a lead throughout the walk.
With its combination of countryside scenery, local history, and engaging storytelling, this walk offers a rewarding opportunity to discover the character and hidden past of one of Kent’s most picturesque areas.