This is a delightful walk with lovely coastal views is the hardest in the book - it has a very hilly ending, and is best done in summer if you would like to swim, otherwise in spring when the woodland floor is covered in bluebells and other wildflowers and, in early May, the gorse is bright yellow. The inland start from Winchelsea is flat to begin with, with just 1 climb for lunch at an excellent and very pretty pub. After lunch the route heads to the coast and follows the coastal path, and there are 4 steep cliffs to climb (with the Fireheights lookout, and Fairlight Glen beach in the middle). Hastings has a 'working beach', a resort beach, and a quaint old town.
Starting below Winchelsea (once a coastal port, but storms have since stranded it 2km inland), the walk follows the River Brede and canals to an early lunch at a 17th century pub near the church in Icklesham. The pub is quaint, and its beer garden has a lovely view, but don't dawdle, less than 5km of this walk is before lunch, and the ending is strenuous.
After lunch, the route crosses two relatively clear streams, both with ill-fitting names: Pannel Sewer and Marsham Sewer, to the coast at Cliff End.
From here, the walk follows the hilly coastline, with sea views. A detour off the coastal route through the houses of Fairlight is required, as a result of severe coastal erosion (an average 1.4 metres of cliff-face is lost annually in these parts). Thereafter you follow the coastline through Hastings Country Park, with 3 steep climbs out of the wooded Warren, Fairlight and Ecclesbourne Glens. The first summit is Fireheights, a coastguard lookout, with excellent views of the coastline. from here on, there are many side paths worth exploring to secluded viewpoints.
The very picturesque Fairlight Glen has a nudist beach where you can drip-dry in fine weather, if you don't happen to have a towel. The path down to it is officially closed due to landslips, but (at your own risk) duck under the fence by the 'closed' signs, and you will find a trail that well maintained by locals. Swimming is good at high/medium tide, not so good at low tide due to rocks. At low tide (but you must follow local advice on this) the adventurous, at their own risk, may be able to walk along the beach from Fairlight Glen to Hastings, past a new 'under cliff' (landslip). It involves rock hopping along the beach - proper shoes required - its harder work than the cliff top path.
Otherwise, the suggested route has more steep climbing till Ecclesbourne Glen, where there has been a fresh landslip. There is either a signed detour inland, or the brave can (at their own risk) attempt the 'closed' path. There have been fresh landslips in this area each winter that have prevented the repair of the path. See Ecclesbourne Glen below.
Finally, you can see Hastings, and you descend down steps into the old town, with its Net Shops on the 'working beach' (tall, black, wooden sheds that were built for hanging out fishermen's nets) and, inland, its lanes and twittens (narrow alleys) of half-timbered cottages. From here, it is a 20 minute walk through the town and along the seafront beneath the Norman castle to the station.
In summer, take sufficient water, and a hat
You could shorten the walk by getting a regular bus back to Winchelsea, or on to Hastings from near the pub at Icklesham to Hastings or a taxi from the pub at Pett Level.
Starting from Rye
As Winchelsea has an infrequent train service, directions are also given to start the walk from Rye. Its a long, flat, peaceful path with views over the levels.
This makes a longer walk of 24km (15 miles). The OS map for the Rye to Winchelsea leg is Explorer 125.
Alternative route from Winchelsea to Icklesham
This route (see section C in the online directions below) takes you from Winchelsea station up into the pretty and historic village of Winchelsea (otherwise not visited on the main walk) and then by an attractive ridge route with fine views to the Queen's Head in Icklesham, the recommended lunch pub. It adds 0.7km (0.4 miles) to the walk length.
Following the Shoreline
Its possible for the adventurous, at their own risk, and on a falling tide only, to follow the shoreline. You must follow local advice on this.
Petts Level to Fairlight Glen beach at low tide only. Note that it is hard going (you have to hop from rock to rock in places), and there is no longer a way up to Fairlight Village (the old path fell into the sea). You pass a deserted beach though - you can see the houses above teetering on the edge due to cliff erosion.
Fairlight Glen beach to Hastings: You pass a new 'under cliff' (landslip). This is a good point to turn back, as after this, its rock hopping along the beach, even at low tide, with no access points - proper shoes required - its harder work than the cliff top path
Winchelsea or Rye Circular
By combining this walk as far as Pett Level with the latter part of Walk 29 Hastings to Rye in Time Out Country Walks Volume 2 (directions also available on this site), you can create either a Winchelsea Circular walk of 16km (9.9 miles) or a Rye Circular walk of 21.4km (13.3 miles). How to join up the two walks is indicated in section D in the online directions below.
The part-Norman All Saints Church at Icklesham contains a variety of architecture styles and has a nave and chancel that are not aligned with one another. A 1592 legacy notice in the church leaves over £3 a year ‘for ever' for highway maintenance.
Ex-Beatle Paul McCartney, who lives a few miles from Winchelsea, funded the renovation of Hog Hill windmill (see map), which is visible from the walk route.
Iron Age chieftains had fortresses on both the east and west hills of Hastings. When the Romans left, the barbarian Haestingas tribe gave its name to the place, having to be subdued by King Offa in 771. William the Conqueror built his first castle here above the town. In 1287 large parts of Hastings were washed away in the Great Storm, the one that left Winchelsea stranded way inland. In medieval times, Hastings was one of the Cinque Ports, supplying 25 ships for 15 days a year for the country's defence purposes, in the days before the Royal Navy existed. (The Cinque ports, pronounced ‘sink’, were Sandwich, Dover, Hythe, Romney and Hastings, plus the two ancient towns of Rye and Winchelsea).
Take the train nearest to 10am from Charing Cross Station to Winchelsea, (or the train nearest to 9am to Rye, if doing the Rye start), changing at either Ashford International or Hastings. Journey time about 1 hour 50 minutes via Ashford or 2 hours via Hastings, depending on the connection. For a premium, you can reduce the journey time to 1 hour 20 minutes by taking the High Speed Train from St Pancras and changing at Ashford. Trains back from Hastings to Charing Cross run twice an hour (hourly in the evenings). Journey time 1 hour 30-45 minutes. Buy a day return to Winchelsea.
If doing the Rye Circular, trains back are hourly, changing at Ashford for either Charing Cross or St Pancras services. Winchelsea has trains every two hours, but the number 100 bus leaves for Rye from outside the New Inn hourly.
Note: There are 3 train routes to Hastings for the Rye / Winchelsea branch line. The High Speed route from St Pancras (change at Ashford International). The longer direct route from Charing Cross / London Bridge. And the even longer route from London Victoria via Clapham Junction and East Croydon. As of 2016, there are cheap 'super off peak' fares on Southeastern Trains from London terminals. In the past the Victoria route was cheapest.
If driving, you can park by Winchelsea station for free, or in Hastings, inland from Hastings County Park. There is a large pay-and-display car park by Rye station. There are half-hourly buses between Hastings, Icklesham, Winchelsea and Rye – routes 100 and 344.
The highly recommended lunch place is the Queens Head (tel 01424 814 552), Parsonage Lane, Icklesham, which serves good food from midday to 2.45pm daily (all day at weekends), but tends to become rather crowded. Booking ahead advisable and essential at weekends. Its nice inside, and the beer garden has a beautiful view. However, this pub is very close to the Winchelsea start, leaving a long afternoon of four hours.
A good alternative lunch pub, closer to mid-point in the walk, in the village of Pett, is The Royal Oak Inn (tel 01424 812 515) with comfortable inside dining areas and a beer garden at the rear. This walker friendly pub has a good, varied menu and serves lunch from 12 noon to 2.30pm Monday to Saturday and from 12 noon to 5.45pm on Sunday. The Royal Oak is an excellent alternative to the Queen's Head when the latter is booked up at weekends, and also makes for a welcoming mid-afternoon stop to take on liquid on a hot summer's day for those who had taken lunch earlier.
Unfortunately, what used to be your late lunch option, the Smuggler Inn at Pett Level, just below the sea wall, CLOSED in 2018 and there are no obvious signs of it reopening (August 2019).
Inland from Fireheights is the Coastguards Tea room. Its approximately four miles before Hastings, and a good place to gather your energies before the steep hills at the end. It does tea and cakes, and serves alcohol. Coastguards Tea Room, Coastguard Lane, Fairlight, Hastings, East Sussex TN35 4AB. Tel 01424 812 902. www.coastguardstearoom.co.uk From the landward side of the radar station (mentioned three paragraphs after point ), take the tarmac lane leading inland, heading for the church. In 300 metres, at the end of a small car park, leave the road to continue straight on, passing to the right of the Hastings Country Park Visitors Centre, up a path between two concrete bollards. In 10 metres this becomes a residential road. The Coastguards Tea Room is 170 metres up on the right.
You go past numerous tea places on the route through Hastings.
On the Winchelsea Circular the New Inn does cakes and tea. The old town in Rye has various options on the Rye Circular walk.