Heathfield is very much a gateway town to both the wonderful High Weald National Landscape and the Low Weald. So if you’re thinking of exploring the area, here are some of the things to do in Heathfield and the surrounding area.
Heathfield
Heathfield is a market town and rights to hold a fair here were first granted in February 1316. The town prospered in the 16th and 17th centuries as a result of the iron industry and again, with the arrival of the railways in the 1880s.
Markets, fairs and festivals
Within the town centre, there are a number of little boutiques and independent shops and cafés. There are also two main monthly markets: the Artisan Market and the Farmers Market. The latter is held on the third Saturday of the month and the Artisan Market is on the first Saturday of the month.
The Heathfield Agricultural Show is an annual agricultural show held in May with livestock competitions, shopping, fresh produce at the farmers market and lots more. The Heffle Cuckoo Fair first started in 1315. Heffle is the old name for Heathfield and according to legend, Dame Heffle would arrive at the fair and release a cuckoo or two to mark the beginning of spring. Sadly, the fair hasn’t been held since the Covid pandemic.
Heathfield Park dominates the area to the east of the town behind a long wall. Within the wall, parts of the park are a Site of Special Scientific Interest and the mansion house dates back to the 17th century and is Grade II listed. It’s now privately owned. Within the grounds, is the Gibraltar Tower. This folly commemorates a former owner of the estate, George Augustus Eliot, who was Governor at Gibraltar during the lengthy ‘Great Siege’ by the Spanish and French of 1779-1783.
High Weald National Landscape
The High Weald National Landscape covers an area of approximately 1,500 square kilometres (560 sq mi) across Sussex as well as Kent and Surrey. It is the fourth largest Area of Outstanding Natural Beauty in England and Wales and is a rolling landscape of woodland, fields, ancient villages and masses of wildlife. Heathfield and Battle sit within this area, with East Grinstead, Haywards Heath and Hastings right on the edges.
The High Weald Walking Festival is held in September each year and for long distance walks in the area, try: the High Weald Landscape Trail, Wealdway, 1066 Country Walk, Saxon Shore Way, Vanguard Way and Sussex Border Path. Or visit Bewl Water and Ashdown Forest.
The Cuckoo Trail
The Cuckoo Trail is a 22.5 km greenway from Heathfield to Polegate suitable for walkers and cyclists. Named after the Cuckoo Fair, it runs along the old disused railway (which was closed in 1968). It’s a wonderful asset to the town and a must visit for those exploring the area.
Markly Wood
To the north of Heathfield, you’ll find Markly Wood and Tilsmore Wood. Some of this is fenced off and privately owned but there is also some great walking in the woods which are very beautiful.
The old railway lines runs north through the centre of the wood and you can access it from the Co-Op car park. From here you can follow the line north for 1.6 km before turning left on to the Sussex Diamond Way and then left again to bring you back to the west end of Heathfield and making a walk of about 5.5 km.
Look out for the old Heathfield railway tunnel and the gorgeous and evocative Victorian railway bridge high over the path. As a shorter and alternative walk, turn north off the High Street up Firwood Rise. At the end, there is an entrance into the woods. Follow the winding path, down and then round through these enchanting woods and you soon come to the top of the steep embankments above the railway line. The path then follows the line until you come to the railway bridge which feels wonderfully wild and abandoned. Cross the bridge, turn left and follow the path until it slowly brings you down onto the old disused line which you can follow back to the Co-Op.
Old Heathfield
Old Heathfield to the south west of the town won’t take you long to to explore. It is pretty, with a church that dates back to the 14th century that has a 14th century piscina and 16th century squint. However, check opening times before you visit. The Star pub next door is pretty with a great garden and was built by the stonemasons as their shelter while building the church.
Folly Trail
Head a little east of Heathfield to Brightling, Dallington and the Mad Jack Folly Trail. If you like crazy but striking follies, a great story, some ancient churches and some fabulous countryside, this is definitely the walk for you.
Batemans
While you’re exploring east of Heathfield, a visit to National Trust property Bateman’s, former home of Rudyard Kipling is also a must.
Mayfield
Head north a little from Heathfield and you come to the hopelessly pretty village of Mayfield. Here you’ll find a wonderful legend about the Devil, some amazing old buildings and a windmill as well as local vineyards.
Hadlow Down
For a small village to the west of Heathfield, you might be surprised to find two main attractions in Hadlow Down, namely, Tinkers Park and Wilderness Woods. Tinkers Park has a collection of steam engines known as the Claude Jessett Collection and they hold steam engine rallies once a year at the end of May and beginning of June. In 2025, they also have a Rail Gala on the 9th and 10th August, as well as their annual open day in September.
Wilderness Woods is a 60 acre community woodland where they have lots of things going on from family bushcraft days to printing workshops, recycled craft workshops and drama summer camps.
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