Rye and Winchelsea (East Sussex) - Free Walking Guide

Ticket to Rye? A Turbostar diesel train en route to the town.

The information on this page may be freely used for recreational walks. It was originally printed as a free guide which was available at the Queen's Head pub in Rye. Beware that some information may change over time. Any known errors will be corrected. Photo by Mark Gostling.

The ancient Cinque Port of Rye is a great base for exploring the diverse scenery of East Sussex. There is a station on the Marsh Link railway line which runs between Ashford, Kent and the coastal towns of Hastings and Eastbourne. It is one of only two remaining diesel lines in the provincial Southern region. Rye has a striking feature in the form of a stone archway known as the Landgate. The Rye Town Model is also well worth a visit. The scenery around Rye is very varied, making the town a great base for walkers. The rivers Brede, Rother and Tillingham meet at the town, and the smaller town of Winchelsea, three miles southwest, is arguably to be the smallest town in England. 

Winchelsea Loop (6 miles)

When exiting Rye Station from the main building, head towards the town past the bus stops on the left-hand side and turn right to walk along Cinque Ports Street. Continue ahead at the junction with the road to Battle, walking along either pavement until reaching a mini roundabout with the A259 near a fish & chip shop.

Continue ahead (signed 'Hastings') and after around 400 yards. take the turning on the left, signed 'Rye Harbour'. Here you will bridge the River Brede. Turn right onto the track. Fork left onto the grassy trail at the houses and follow this for a mile, with views of Camber Castle to your left. This was built by Henry VIII. The modern-day village of Camber is actually located several miles away on the opposite side of the Rother estuary. The path bears left as though heading towards the castle and then turns right to continue running along a grassy ridge.

The path rejoins the river-bank for a bit and later bears left to pass through a gate. Continue ahead on the concrete drive and onto a lane at the second gate. Upon reaching a larger road, turn right and walk for half a mile to the end of the road.

At the T-junction with the A259, turn left, and after passing the former Bridge Inn (now a house on the right) turn left again, climbing the steep hill into Winchelsea. Winchelsea has a claim on being England's smallest town and it is thought that it once possessed around ten times its modern day population.

Winchelsea was laid out in a grid pattern in the 13^th century, like a quaint precursor of Milton Keynes! You will pass around the stone arch Strand Gate, one of three which mark the ancient entrances to the town. At the top of the hill continue straight ahead, passing the churchyard to your left. Comedian Spike Milligan is buried here and there is a well-trodden path through the grass to this location. St Thomas' Church is worth entering, not least to discover Winchelsea's influence on famous paintings.

At the New Inn pub, turn right, and then left at the next junction. Cross the A259 at the end of the road (with views of the Pipewell Gate to your right) and continue ahead along the drive on the other side. Follow the footpath ahead passing a beacon which marks the site of an ancient windmill. Continue, descending into the Brede Valley, bearing right around the hillside as you go. Keep bearing right to pass through a gate and over a small footbridge into trees, eventually reaching the road again. Turn left onto the lane signed 'Winchelsea Station'. Cross the railway line and follow the lane onward towards the hills. At the end of the lane, turn right onto the curiously named 'Dumb Woman's Lane.' Where this lane turns sharply left to climb the hill, continue ahead along the bottom of the hills on the trackway. This route can also be cycled as it forms part of the South Coast cycle route.

When the track becomes a small lane near houses, turn right to follow the path. After passing a car park, turn right opposite the windmill and cross the railway line. You will exit onto the A259 where you can turn left to retrace your steps to the station, but don't miss out on Rye town centre before you leave.

Leasam / Houghton Green Loop (4 miles)

When exiting Rye Station from the main building, turn right to pass a large supermarket. When you reach a level crossing at the end of the road, turn right to cross the railway and continue down the alleyway to the right of the former Queen Adelaide pub.

Continue ahead on this path towards the hills. At the end you will see a footpath with steps climbing steeply ahead. Take time to savour the view behind as you climb.

At the top, follow the gravel trail through a cemetery, bearing right when you pass a small chapel. The tarmac drive will bring you out onto the A268. Cross the road and turn left to follow the pavement passing the Playden Oast Inn. After two thirds of a mile you will come to a turning on the right, just before the T-junction with the B2082. Turn down the lane towards Houghton Green and follow it around a sharp left-hand bend.

100 yards after the bend you will see a public footpath on your right hand side. Follow this along the field edge which gradually bears left. Continue into the next field, walking beside the hedgerow on your right. Soon you will come to a bridge over a stream. Bear left at the stile after the bridge and follow the bottom (left) edge of the field, continuing into the next field in the same direction. Eventually you will reach a lane. Bear right.

At the end of this lane, turn left, taking great care walking along the road. The cliffs here once formed part of the ancient coastline when Romney Marsh was covered by the sea. Cross the bridge over the River Rother on your right when you reach a dam, and then turn right to follow the Royal Military Canal Path along the east bank of the waterway with views of the Cheyne Court wind farm.

Follow the bank for a mile and a half, eventually passing beneath the railway bridge and coming out onto the A259. Cross the road and turn right along the pavement, bridging the river. Continue ahead at the mini-roundabout and cross the road again at the lights, climbing the slope on the opposite side. You can explore the town centre by turning left at the top. To return to the station, turn right at the top to pass beneath the Landgate arch and turn left onto Cinque Ports Street, looking out for the station approach on your right as you continue.

One-way route to Hastings (13 miles)

A long-distance walk for seasoned ramblers:

Follow the first three paragraphs of the Winchelsea Loop but before you bridge the Royal Military Canal to reach the A259, turn left onto the canal path to follow the south bank south-westward. The canal is a 28-mile waterway which was built as an obstruction against a feared invasion by Napoleon. It is the third longest defensive structure in the UK (after Hadrian's Wall and Offa's Dyke). This area of marshland is known as Pett Level, and this southernmost section of the canal is much narrower than the section from north of Rye to Appledore, Hamstreet, Hythe and Seabrook. There is a sister blog post on walks from Hamstreet which explore the Kent section of this waterway.

Remain on this side of the waterway for the next three miles. Be prepared: you may encounter long grass and weeds in places. Continue ahead when you eventually cross a concrete drive.

Cross the bridge over the canal at this point and continue to the end of the canal along the north bank. Turn right at the road - you will pass the former village shop of Pett Level (now a private house). There used to be a pub in the village called the Smuggler too. Bear left at the T-junction to follow the main route towards Fairlight. Take extreme care as you walk for a mile along the road around some right-angle bends.

Soon you will reach a track to your left just before the road bridges a stream. Take this shady trackway and continue straight ahead at each of the junctions, climbing past houses. Beware that this can be wet / muddy. Eventually Lower Waites Lane becomes Smugglers Way which bears left and climbs steeply. Turn right at the end onto Bramble Way. At the end of this road turn left to reach the cliff-top Saxon Shore Way track. Turn right here, climbing towards Hastings Country Park. A footpath continues ahead on the left side where the track becomes private.

Each time there is a fork, take the left path to remain following the cliff-edge (also follow the marker posts for Hastings). After passing a lookout tower to the right you will descend into three deep glens (Warren Glen, Fairlight Glen and Ecclesbourne Glen). The views are stunning but a certain level of fitness is required as there are a lot of steps. At the final descent into Hastings the route opens up into a wide green, heading towards a beacon. The green eventually funnels towards a series of steps down beside the East Cliff lift. At the bottom of the steps, continue straight down the hill and cross the A259 at the bottom. Continue ahead into Hastings Old Town on Courthouse Street.

Turn left at the T-junction with High Street, Then take the 2^nd turn right into George Street. Continue onward when you emerge back onto the A259 and bear right at the roundabout to go through the underpass and into the pedestrianised area. At the large junction of streets, take Havelock Road which continues ahead past the John Logie Baird pub and curves to the right. Continue ahead at the traffic lighted junction to reach the station to catch your train back to Rye.

A humorous travelogue by the author of this blog is available. Check out 'Mud, Sweat & Beers' today!

The South Coast Trunk Road (Part II)

[Last updated January 2020]

Last time I left you stranded near Pevensey in East Sussex. This month we complete the South Coast Trunk Road narrative (purloined from a withdrawn web page of mine) with a large portion of A259.

Nicknamed as the ‘world’s worst trunk road’ by some, this road is of a reasonable standard to begin with, being a long, tree-lined straight (actually some of the gentlest curves imaginable). It then bears smoothly right and climbs, suddenly winding back and forth at the top, before slowing right down to enter unbanity (or ur-banality) for the next ten miles, beginning with Little Common. There is a 30 limit for much of this section.

Bexhill (apparently the home of British motor racing) presents us with one roundabout and a box junction where the A2690 uses a former railway trackbed to bypass the suburbs to reach the A21. Personally I think it would be better utilised by number it as an extension to the A28 as a signed route to Ashford, avoiding the urbanity that is follow on the A259.

So, back to the A259, there is a brief rat-race climb, where the road briefly flirts with dual carriageway around the back of the town centre, quirklily named King Offa Way. Then it plunges back into urbanity with a long, slow straight all the way to the out-of-town entertainment complex that marks the border with Hastings.

After Bulverhythe, the road passes under the railway bridge and finds its way to the sea, running along the promenade of St Leonards, all the way to Hastings, where the greensand escarpment above the old town is ever prominent, crowned with its castle. Apart from Dymchurch and Sandgate on the now-detrunked part of the A259 (Kent), this is the only point that the South Coast route truly hugs the coast.

At the centre of the ‘birthplace of television’, you will pass the pier and fun fair to your right. This epithet is due to John Logie Baird once residing in the town. I have heard that notable births in Hastings include Suggs (of the band Madness) and funny person, Jo Brand.

Beyond a completely pointless roundabout, you will pass the old, black, wooden fishing sheds. The A259 then dives inland for a sustained climb of almost a mile through the suburban housing, to Ore. Trumped ambitiously as ‘Ore Village’, the road forms the main shop-lined street here, and a short climb later, it presents the motorist with breath-taking views before its steep descent.

There used to a crawler lane all the way up the hill for traffic coming the opposite way. This has been shortened in recent years – maybe an attempt at traffic calming!

Beyond Guestling, the road narrows, then winds, then narrows some more, and regains its confidence for a mile or so before Icklesham, which has a windmill. The road regains momentum again beyond this pleasant village, with an impressive descent followed by the resulting climb to Winchelsea – Britain’s oldest ‘new town’, laid out in a grid pattern in the 13th century – well worth a visit and often quoted as ‘England’s smallest town’. Spike Milligan is buried in the churchyard, with 'I told you I was ill' in Gaelic etched on his stone (the same phrase in Engish being deemed too irreverent!).

The A259 has no such interest, and passing one of the three stone archways, it drops steeply down the wooded hillside with a sudden hairpin-bend at the bottom. After a bumpy ‘risk of grounding’ undulation, it uses straight lines along the banks of the Royal Military Canal to plot its narrow route across the marshes to Rye, a larger town which successfully contorts the A259 by 180 degrees to cross the River Tillingham, before hiding it away between the southern undercliff and its Victorian terraces. The Rye town model in the tourist office is a fascinating glimpse of the town's history.

After another mini-roundabout and a narrow bridge over the River Rother, the road streaks purposefully in a dead-straight line out onto the vast expanses of Romney Marsh – totally flat, pastoral, grazing land which remains so for the next 13 miles of our route. This speedy beginning is deceptive - at East Guldeford there's a chicane between two level crossings, and two right-angle bends follow, first right and then left, where we cross the border into Kent.

The Cheyne Court wind-farm is ever present here. After two more right-angle bends, the A259 remembers that it is a trunk road, widening and straightening out, through-passing Brookland with a 50 limit and roundabout. It used to run through the pretty High Street, sadly now devoid of basic amenities, however Brookland's church is worth a visit as its steeple is on the ground! You will barely notice the level crossing as you speed towards Brenzett – the transport hub of the marsh.

The next section is a real ‘rags to riches’ story. From the 2070’s humble beginnings as a B road from New Romney to Ashford, it has now usurped the Brenzett to Folkestone section of the A259, which has been detrunked, due to being a predominantly urban crawl through a series of coastal towns and villages.

The new route is a top-grade single carriageway to Ashford. The road has even been recommended for speed trails by motorcycle magazines – not advised! The terrain is completely flat, passing the hamlet of Snave towards the gently curving section that climbs the clay hills around Hamstreet – worth a detour for its typically Kentish weather-board buildings, and once featured on a set of UK postage stamps. We cross the Royal Military Canal again as we climb onto the ridge of clay hills. The canal was built as a barrier against a feared attack from Napoleon and is the UK's third longest defensive structure.

Beyond this village, the road is almost motorway-like, although still a single carriageway, with five bridges and only one further junction. It climbs through forest which was once part of the great forest of Anderida which covered the whole of the Weald. The picture at the top of the page is of this section. Our road then follows the railway line dead-straight across flat farmland until the roundabout serving the sprawling southern estates of Ashford.

A mile later, the A2070 reaches another roundabout and enters a brief 50 limit, to spiral up sharply onto the dual carriageway Southern Orbital road. This is now the land of business parks, and it is due to become much more urbanised as time goes on, with the proposed expansion of Ashford. Within two miles, you will cross another two roundabouts, taking the dual carriageway to junction 10A on the M20 which opened in 2019 which is where our trunk route ends, as the M20 steals its thunder towards Folkestone and Dover. It's been emotional!

The South Coast route as described is no longer used as a general east-west route, with most patrons opting for the M20, M26, M25 and a suitable conduit southward (M23/A3/M3/A303). Although efforts have been made to improve some parts of this road (Brighton bypass/Polegate bypass/Hamstreet bypass), it is hoped by many locals that no full-scale upgrade of the entire route occurs. In the interest of the countryside that remains along this varied route, they may just have a point.