High Weald Landscape Trail

Total distance covered; 102 miles (162kms)
8 days walking (plus a rest/relocation day) based in Royal Tunbridge Wells and Rye

visit our tour base - Royal Tunbridge Wells

visit our tour base - Rye

The High Weald Landscape Trail is a 95 mile (152kms) route which traverses the High Weald AONB (Area of Outstanding Natural Beauty) from the Sussex town of Horsham in the west, to the Cinque Port of Rye in the east. 

In early medieval (Saxon) times the whole area was heavily wooded and swineherds drove their herds into the forest from the coastal settlements to fatten their pigs on acorns. Gradually seasonal shelters and small clearings grew into larger settlements and villages, but the main change in the landscape came in the 15th century when the invention of the blast furnace turned the High Weald into the industrial powerhouse of Tudor England. Swathes of the forest were felled to provide timber for charcoal to fuel the iron industry, and also to build ships for the fast growing naval fleet, so large areas of land became available for grazing, orchards, and the growing of hops. 

  iStock-481475426, Footpath near Rye


Nowadays the iron industry is long gone and the quiet rural landscape of the High Weald is characterised by ribbons of deciduous woodland interspersed with patches of heathland, pasture, hay meadows, arable fields, orchards, hop gardens, parkland and, in the east, marshland grazing. In the attractive villages evidence of local building materials abounds, with many houses timber-framed and built with hand-made bricks fashioned from local clay, often with tile-hung frontages, weatherboards and steep tiled roofs.


iStock-1128256661, Kent wild flowers 

Highlights of the High Weald Landscape Trail include the views across to the South Downs from the wealden ridge; the sight of oasthouses and windmills; Harrisons Rocks where the sandstone outcrop is a haven for climbers; the handsome brick facade of Benenden School; the views of the surrounding marshes from the landlocked Isle of Oxley, the charming villages of Slaugham, West Hoathly, Hatfield, Goudhurst and Matfield, with their attractive village greens, medieval cottages and churches; the historic towns of Tunbridge Wells, Cranbrook and Tenterden and the sight of the Ypres Tower as we enter the ancient town of Rye, the end point for our walk.  

  iStock-1059598814, Goudhurst


To keep the transport journeys to/from the start/finish of each day's walk manageable, the holiday has been split between two bases, Royal Tunbridge Wells and Rye, with four days walking from each, and a rest/relocation day in between. 

Visit our tour base - Royal Tunbridge Wells

Visit our tour base - Rye

What's included in the price of this holiday?



Holiday Options 2021

Date:May 16 - May 24, 2021
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Daily Itinerary 

Day 1: Horsham to Cuckfield  15 miles (24kms)
Day 2: Cuckfield to West Hoathly 11 miles (18kms)
Day 3: West Hoathly to Hartfield 14 miles (22kms)
Day 4: Hartfield to Royal Tunbridge Wells 15 miles (24kms)
Day 5: Rest/relocation day
Day 6: Royal Tunbridge Wells to Horsmonden 14 miles (22kms)
Day 7: Horsmonden to Benenden 12 miles (19kms)
Day 8: Benenden to Wittersham 13 miles (20kms)
Day 9: Wittersham to Rye 8 miles (13kms)



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