Dan Hobson

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

On The Map

Tours & Highlights

    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 centre, hike south to Mick’s Cross and then southeast along greenlanes to Slaugham.

    Next, the trail heads south through gently-undulating farmland to the outskirts of Warninglid, before following Colwood Lane to Wykehurst Corner. Here, it descends steadily through Malthouse Wood to Bolney village, which has a couple of places for food and drink, should you fancy a pit-stop.

    After crossing under the A23, wind through Bolney Wood, skirt the tip of North Wood and follow Pickwell Lane along the edge of Raggat’s Wood. You then take footpaths through Black Forest and Long Wood, emerge into farmland and head east through Cuckfield Park.

    Right before the finish, you pass Holy Trinity, a beautiful Grade I-listed church from the 12th century. A short step later, you finish in the village of Cuckfield, which has accommodation and places for food and drink.

    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 hike, read on.)

    From Cuckfield, hike north through Whiteman’s Green and head right after Lower Spark’s Farm. Footpaths lead east to Borde Hill Gardens, at which point country lanes take you over the railway line and alongside Wickham Wood.

    Next, hike north along tree-lined footpaths, cross the railway and continue through River's Wood into farmland. At Ardingly Reservoir, head east through trees, around Saucelands Pond, past Ardingly College and through Standgrove Wood.

    The trail then heads to Ardingly, snakes north along lanes and footpaths, winds through Chiddinglye Wood and ascends to a high point in West Hoathly. If you wish to split the stage, both Ardingly and West Hoathly have accommodation and options for food and drink.

    You follow lanes out of the village and then descend along footpaths through Whitestone Wood, past Lower Lake and through Warren's Wood. At Bushy Wood, head south alongside the Bluebell Railway heritage line, which you eventually cross. A short time later, cross the River Medway and hike over Stone Farm Rocks, which were formed 140 million years ago.

    A short but sharp climb takes you from Weirwood Reservoir past Standen House, before a steady descent around Dunning's Wood and into East Grinstead. Here, you find an excellent choice of accommodation and places for food and drink.

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  • Difficult
    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 the former Tunbridge Wells railway line, which closed in 1967, southeast to Forest Row.

    Next, rise steadily north through fields, skirt Hazel Wood, and then bend east along serene footpaths to Hartfield. Here, the trail crosses fields to Withyham and then snakes southeast through farmland and woodland over gently-undulating terrain around Lye Green and onto Groombridge.

    When you reach the village, a worthy detour is heading onto Groombridge Place — a beautiful country estate complete with sculpted formal gardens, a moated 17th-century manor house and over 200 acres of parkland — and finishing at a pub that was once the headquarters for a band of ruthless smugglers, the Groombridge Gang.

    There is limited accommodation in East Grinstead. However, there is a train station which provides regular services to Royal Tunbridge Wells, a vibrant town with plenty of choice.

    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 is popular with climbers. The trail then heads east through farmland to Eridge Rocks, another ancient rock formation hidden amongst the trees.

    Next, head through Eridge Green village into Mill Wood and rise along the edge of Whitehill Wood to Frant. The trail then descends steadily through woodland and farmland to the outskirts of Tunbridge Wells, where it crosses the county border into Kent, and continues northwest to Pembury along lanes and footpaths.

    The final section loops east around the edges of Snipe Wood and Brenchley Wood to Matfield, which boasts a pretty village green dominated by a handsome Grade I-listed manor. There are some accommodation options and places for food and drink around the village. However, places to stay are limited. Pembury also has options.

    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, continue south to the outskirts of Horsmonden and follow green lanes through woodland.

    Next, the trail zig-zags through orchards, heads south through fields and joins country lanes at Lordship Wood. You continue along lanes over the River Tesse to Trottenden Farm, before ascending along tree-lined footpaths to Goudhurst, which boasts a Grade I-listed church and places for food and drink if you fancy a pit-stop.

    The trail then curves southeast through expansive farmland and clusters of trees and eventually rises into Angley Wood, an atmospheric woodland composed of chestnut, birch, hazel, beech, oak and pine. From here, it is a short step to finish in Cranbrook, where you find accommodation, places to eat and drink, quirky shops, galleries, and other attractions.

    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 town, before heading southeast though pastures, arable land and small woodlands to the outskirts of Benenden.

    After crossing the B2086, you follow a Roman Road for a short time before looping into Benenden, which has a 14th-century church on the village green and a community cafe which is perfect for a pit-stop.

    You follow the road out of the village and then take serene footpaths southeast through expansive farmland and pockets of woodland. At Woodcock Lane, the trail heads east and picks up footpaths to Rolvenden.

    Next, head south to the hamlet of Rolvenden Layne and then hike northeast along footpaths through open fields to Tenterden, affectionately known as the ‘Jewel of the Weald’. Within the town you really are spoilt for choice in terms of places to stay, eat and drink, as well as shops and other attractions.

    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 continues to soar in popularity.

    You leave Tenterden to the south and follow footpaths through farmland and clusters of woodland to Small Hythe, which was, astonishingly, a thriving medieval port. Here, you also find Smallhythe Place, an early 16th-century house and cottage gardens owned by the National Trust, and the Chapel Down vineyard and winery.

    The trail then rises through fields to Wittersham, heads southwest to the River Rother. Here, you join the Sussex Border Path (komoot.com/collection/1059197/a-historic-hike-through-medieval-landscapes-sussex-border-path) for a short distance before peeling away east to Peasmarsh.

    You drop from higher ground near Peasmarsh into the Tillingham Valley and follow the river through old orchards and grazing land to finish in Rye.

    Within the charming little East Sussex town, you find cobbled alleys lined with historic buildings that are filled with quirky shops, cafes, eateries and more. There is an excellent choice of accommodation, too, as well as a train station.

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Collection Stats

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

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