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Hike the medieval heart of the South East — High Weald Landscape Trail

antonychammond (CC BY-NC-SA 2.0)

Hike the medieval heart of the South East — High Weald Landscape Trail

Hiking Collection by Dan Hobson

7-14

days

3-6 h

/ day

98.7 mi

6,600 ft

6,750 ft

The High Weald Landscape Trail is a long-distance hike that explores ancient woodlands, rolling pastures, orchards, vineyards, sandstone crags, medieval farmsteads and historic villages in the rural heart of South East England.

Crossing the counties of West Sussex, East Sussex, and Kent, the route visits some of the most picturesque parts of the High Weald Area of Outstanding Natural Beauty (AONB). You can expect varied walking, ever-changing views, abundant wildlife, captivating history and a real sense of solitude throughout.

The trail begins in the market town of Horsham and meanders southeast through St Leonard's Forest, Cuckfield, East Grinstead, Groombridge, Royal Tunbridge Wells, Cranbrook, and Tenterden to finish in the historic town of Rye. The official route is 95 miles (153 km). However, with a couple of detours to some worthy sites, this Collection totals 99 miles (159 km).

The High Weald is an area that has been sculpted by humans throughout the ages. Its first inhabitants were Mesolithic hunter gatherers some 10,000 years ago. All the subsequent civilisations — Neolithic, Bronze Age, Iron Age, Roman, Saxon — have left their mark, too.

During the medieval period, the population of England increased three-fold and the High Weald became a vital food source. The temporary settlements created by seasonal pig herders became permanent farmsteads, the likes of which can still be seen today. Whilst the area went on to have a booming iron industry, the Weald is still considered to be a medieval landscape.

Highlights along the way include: St Leonard's Forest, a historic woodland packed with wildlife and legend; Stone Farm Rocks; a sandstone crag formed 140 million years ago; East Grinstead, a market town with one of the longest stretches of 14th-century timber-framed buildings in England; Eridge Rocks, an ancient crag with unique plant life; Cranbrook, the ‘Capital of the Weald’; Union Mill, a working smock mill from the 1800s; Smallhythe Place, a stunning 16th-century house; and Rye, which boasts an abundance of historic sites.

The geology along the trail switches between sandstone and clay, the latter of which can be muddy in wet conditions. As such, sturdy, waterproof boots are recommended in all but the driest weather. Other than that, the walking is generally leisurely throughout, owing to the gently-undulating nature of the landscape. Paths are well-maintained and waymarked, making the route a good choice for all abilities.

In this Collection, I split the route into seven stages, averaging 14 miles (23 km), heading west to east. As Stage 2 is above average distance, I suggest how you can split the hike. Of course, you can divide the Collection into as many days as you are comfortable with or walk any single stage. Public transport links are generally good along the trail. The choice of which direction to walk is entirely yours.

You are reasonably well-served by accommodation throughout. However, places to stay are not always abundant so it is worth planning in advance and booking ahead. Places for food and drink are plentiful en route, too.

Getting to the start and finish of the trail is easy as Horsham and Rye both have railway stations, good public transport links and are served by arterial roads

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High Weald Landscape Trail

95.0 mi

6,475 ft

6,650 ft

Last updated: November 11, 2021

Plan your own version of this adventure in the multi-day planner based on the stages suggested in this Collection.

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Tours & Highlights

  • Difficult
    06:26
    14.9 mi
    2.3 mph
    1,050 ft
    925 ft
    Expert Hiking Tour. Very good fitness required. Mostly accessible paths. Sure-footedness required.

    The first stage winds through West Sussex countryside dotted with ancient woodlands, chocolate-box villages and pretty mill ponds.

    

    From Horsham Station, the trail heads east out of town and follows tree-lined footpaths into St Leonard's Forest, an extensive woodland with abundant wildlife. In the forest

    by Dan Hobson

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  • Difficult
    07:40
    17.4 mi
    2.3 mph
    1,500 ft
    1,425 ft
    Expert Hiking Tour. Very good fitness required. Mostly accessible paths. Sure-footedness required.

    Steam railways, rocky crags, rolling woodland and lake views combine on this stage, which leads you to the historic town of East Grinstead.

    

    The most challenging route in this itinerary, Stage 2 is 17.4 miles (28 km) long with 1,500 feet (457 m) of elevation gain. (For a suggestion on how to split the

    by Dan Hobson

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  • Difficult
    06:33
    15.3 mi
    2.3 mph
    800 ft
    1,000 ft
    Expert Hiking Tour. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

    This stage winds through picturesque patchwork countryside on a journey from West Sussex to East Sussex.

    

    To begin, the trail passes some of East Grinstead’s most historic buildings, including the 11th-century Church of St Swithun and Sackville College, a Grade I-listed Jacobean almshouse. You then follow

    by Dan Hobson

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  • Difficult
    06:09
    14.1 mi
    2.3 mph
    1,125 ft
    1,000 ft
    Expert Hiking Tour. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

    Ancient rock formations and glorious views await on this hike, which explores the rolling landscape south of Royal Tunbridge Wells and leads into Kent.

    

    You leave Groombridge to the south and wind around Birchden Wood. At the southeast corner of the woodland lies Harrison's Rocks, a sandstone crag that

    by Dan Hobson

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  • Intermediate
    04:59
    11.4 mi
    2.3 mph
    825 ft
    900 ft
    Intermediate Hiking Tour. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

    Stage 5 snakes through orchard country to the ‘Capital of the Weald’, Cranbrook, which boasts medieval streets and a historic smock mill.

    From Matfield, hike southeast through farmland dotted with hamlets and pockets of woodland to Brenchley. You then head through a vast orchard, skirt Furnace Pond

    by Dan Hobson

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  • Difficult
    05:30
    12.8 mi
    2.3 mph
    725 ft
    775 ft
    Expert Hiking Tour. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

    You can expect varied walking and ever-changing views on this hike, which continues through the glorious rolling pastures of Kent.

    

    To begin, it is worth sauntering through the medieval streets of Cranbrook to Union Mill, a Grade I-listed smock mill from the 1800s. You rejoin the trail in the north of

    by Dan Hobson

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  • Difficult
    05:32
    13.0 mi
    2.3 mph
    600 ft
    775 ft
    Expert Hiking Tour. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

    The finale explores a picturesque landscape where vineyards thrive and medieval history survives.

    

    The countryside around Tenterden historically produced apples and potatoes. However, due to its temperate climate and well drained south-facing slopes, grapes are the hot crop these days and Kentish wine

    by Dan Hobson

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Questions and Comments

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Collection Stats

  • Tours
    7
  • Distance
    98.7 mi
  • Duration
    42:49 h
  • Elevation
    6,600 ft6,750 ft

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Hike the medieval heart of the South East — High Weald Landscape Trail

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