This final leg of the High Weald Landscape Trail is a delightful blend of Kentish rural charm, winding through orchards and gentle hills before descending to the medieval town of Rye, set just a few feet above sea level.
Our walk begins in Tenterden, the “Jewel of the Weald”, with its gracious brick-and-tile buildings. A highlight early in the walk is Smallhythe Place, a beautiful 16th-century timbered house that was once the home of actress Ellen Terry. Soon after we enter Tilder Gill, a serene valley bordering a woodland stream.
Emerging from the glen, the route leads across the Isle of Oxney, once surrounded by rivers and marshes, this low-lying “isle” offers wide views over farmland and meadows yet now the area is dominated by pastoral fields and Chapel Down vineyards, their neatly ordered rows a sign of Kent’s flourishing wine production.
Continuing south, we cross back into East Sussex, traversing the old Rother River floodplain, wetlands, willow-lined paths, and polders. Look out for traces of early industry, hammer ponds and ancient waterworks, echoes of the region’s medieval iron-making past.
We will stop at suitable place for lunch, please bring a packed lunch
The journey culminates in Rye, providing a grand and historic finale to the trail. Arriving at Strand Quay, near the confluence of the River Rother, walkers are welcomed by the cobbled charms of Mermaid Street famous for its crooked, characterful medieval buildings and timeless atmosphere. There are ample options for a celebratory drink or meal.
Travel: We will catch the train from London Victoria at 9:31, arriving at Headcorn at 10:39. We then take the 10:53 Bus 12 at Headcorn Station (outside the station) and ride for about 20–25 minutes to Old Post Office, Tenterden.
In our way back we might catch the Rye → Ashford International → London St Pancras train (via Southeastern/Southern) at 17:48.
No booking required.
The finishing time is an estimate only and will be dependent on a number of factors such as, weather, the speed at which the group walks and the number of breaks taken.