Winchelsea to Hastings via Three Oaks walk

The 1066 walk route through pleasant hilly territory from Winchelsea to Icklesham and Three Oaks, then south over a ridge to the sea at Fairlight. A strenuous finish into Hastings.


This is a list of previous times this walk has been done by the club (since Jan 2010). For more recent events (since April 2015), full details are shown.

Date Option Post # Weather
Sat, 10-Jun-23 Winchelsea to Hastings via Three Oaks 13 blazing hot sunshine
Sat, 01-Aug-20 From an Ancient Town to a Cinque Port Town via a Mediterranean Dip 22 fine clear skies with a cooling sea breeze
Sat, 29-Jun-19 Saturday walk - Winchelsea to Hastings via Three Oaks [New walk] 17 hot

Length: 26.4km (16.4m) / 13km with one of the shortcut options
Toughness: 9 / 10
Transport: Take either the 9:37 from London St Pancras to Ashford and change there to the train to Winchelsea arriving 10:52, or take the 8:38 from London Charing Cross to St Leonards Warrior Square and change there to the train to Winchelsea arriving at 10:43. Return trains from Hastings at xx:25 to London St Pancras and London Victoria, xx:21 and xx:46 to London Charing Cross.

This is a great summer walk. Instead of following the coast to Fairlight as some other walks do, it turns inland to follow the edge of the River Brede valley. Lunch is at the delightful Three Oaks pub before the walk winds its way through woodlands and across undulating hills to the coast. There, you keep to the usual exhilarating coastal route with steep climbs and descents along the cliffs to Hastings. You should pass the beach at Fairlight Glen at about high tide for a refreshing swim.

You can shortcut the walk by either finishing it at the station at Three Oaks (13km) and missing out on the coastal scenery, or starting the walk at Three Oaks (13.5km).

  • 10-Jun-23

    5 assembled at the start of this walk and doubtless enjoyed a fine morning in pleasant scenery. 4 of them arrived at the lunch pub in Three Oaks at around 2pm (??)….where they met us, just leaving. We were 4 people who got the 10.38 train from Charing Cross (10.47 London Bridge) and then changed at St Leonard’s for a train to Three Oaks, arriving 12.35. We did a short circular “appetiser walk” and then enjoyed a fine lunch, with huge portions.

    When the long walkers turned up, we decided, in time-honoured SWC tradition to “wander on ahead”. We set out across flowered-filled (though in places a bit drought-parched) countryside in blazing hot sunshine to climb the mighty ridge to Fairlight. The weather forecast had suggested cooler temperatures on the coast. Reader, it was wrong.

    Having reached the snow-flecked pastures at the top of the ridge, we eschewed tea in favour of the short cut to the coast path, and jostled our way down the naturists’ path to Fairlight Cove. The tide here was at the full and the beach fairly packed. Two swam, the others paddled. We also met a Brighton-based SWCer here who had done the full walk but started an hour early. So 10 on this walk in all.

    I had expected a brief cold swim. But the hot sun had done its work and the water was gorgeous. I went further out than I have been all year and there encountered what I first thought was flotsam, then a wet-suited diver, but finally realised was a seal. Moments later it resurfaced about 30 metres away from me and gave me a curious stare. A lovely moment.

    We lingered on the beach for an hour, hoping the long walkers might turn up. I had a second swim and the seal came in quite close to the shore. Eventually we left. The others turned up shortly afterwards, I guess, and four of them swam.

    In Hastings we short walkers found a quiet pub in the back streets of the Old Town. Despite having walked “only” nine miles, we felt very adequately exercised. One left to get the 19.46 train. The remaining three surveyed the seafront chippies and found the Codfather had an offering we couldn’t refuse. We met two of the longer walkers, one of whom joined us on the 20.21 to Charing Cross. The journey flew by, aided by two bottles of cool white wine.

  • 11-Jun-23

    2 more got the posted train but started from Three Oaks, so that's 12 if we are counted. We got to the beach at Fairlight about three and had a paddle - I see what you mean about the rocks making it tricky to get in the sea at mid-tide. Then we repaired to the Royal Standard in Hastings for drinks with a friend of my companion, fish and chips and the 1825 train (jam-packed from Ashford). it was a bit too hot for me but all in all, a really nice alternative to the more well-trodden walks to Hastings.

  • 14-Jun-23

    PS I’ve since heard that one other started from 3 Oaks an hour earlier than us, making 13 altogether at 5 different start times/points!

SWC 316: Winchelsea to Hastings (via Three Oaks) T=swc.316

Distance: 16.4 Miles or 26.4 km for those more metrically minded (with options to shorten to about 8 miles by starting or finishing in Three Oaks -- see walk notes)

Difficulty: 8 out of 10

Train: Take the 9:34 AM train from London St. Pancras to Ashford International and change onto the Southern service to Brighton (arriving 10:11 and departing 10:25) to arrive in Winchelsea at 10:51. Return trains from Hastings are regular and varied: to Charing Cross 17:18; 17:50; 18:18; 18:50; 19:50; 20:50 and 21:50 to Victoria 17:23; 18:23; 19:23; 20:23 and 21:26 and to St. Pancras (via Ashford) 17:27; 18:27; 19:27; 20:27 and 21:27. Buy a day return to Hastings.

This walk features a new twist on an old favorite. It starts off rather innocently in a gentle (almost misleading) way across Romney Marsh on the 1066 path from the delightful Ancient Town of Winchelsea and finishes with a bang with a few steep climbs along coastal cliffs and an opportunity for a cooling idyllic swim in an almost Mediterranean cove towards the end (who needs Spain). You can find more information about the walk and download the walk instructions here.

Lunch is probably still advised as a picnic – but the Three Oaks Pub in, well you guessed it, Three Oaks (01424 813 303) about 8 miles/12.9 km into the walk is open according to its website. Although sadly, I think the Coastguards Tea Room is closed, the old port in Hastings offers a variety of refreshment options at the end of the walk.

Enjoy the walk and swim!

  • Anonymous

    Due, probably to the coronavirus, the last bus out of Fairlight is now 16.58 (5 o'clock) and not 18.58 (7 o'clock) as indicated in the walk notes.

  • 31-Jul-20

    Just rang The Three Oaks and they are doing food. I'll eat there. Lovely pizza last time I was there. Gavin

  • 31-Jul-20

    I just checked the tides at Hastings for tomorrow: Low tide at 15:58. Dooh. No swimming at Fairlight Glen then. Hastings beach might still be fine.

  • 31-Jul-20

    Why is low tide not good for swimming.

  • 31-Jul-20

    Why is low tide not good for swimming.

  • 31-Jul-20

    As for tides, I think low tide will actually be an hour later, taking in BST....which should make it ok...very low tide means you can negotiate out through the rocks, as they will be exposed....the problem period is mid-tide when you can't see rocks...but the tide is not high enough to swim out over them....

  • 31-Jul-20

    Low tide is 16.56 BST, according to the BBC

  • 31-Jul-20

    Yes, low tide is 15:58 GMT, i. e. 16:58 BST. Didn't read this correctly. Let's see how it will look.

  • 02-Aug-20

    Gosh, where to start....a really fab day, aside from a somewhat crowded train from London and a very crowded one from Ashford to the end 17 emerged on the platform at Winchelsea and set off breaking into smaller groups under fine clear skies with a cooling sea breeze . In Winchelsea we encountered 2 regulars who joined us for a spell before they circled back to Winchelsea at Icklesham. The rest set off into what was new territory for some with lovely rolling hills and great views. Most picnicked a top a hill with vast views about a mile before the pub in Three Oaks, then went to the pub for a drink and met with the pub lunchers. The walk then climbs up to the cliffs from the back which provided an interesting perspective. Once on the cliffs, most opted for the slight short cut to head direct to the swimming cove...though a few opted for an easier finish avoiding the big dips along the coast into Hastings....As for the swimmers, on the beach we found one early starter and two late Three Oaks starters...the tide was at the "peak" of low and one could easily walk around the rocks into the the very pleasant (though slightly lively) water with a very Mediterranean backdrop...absolutely gorgeous....After our refreshing dip, we continued into Hastings and reconnected with some who had done the easier finish, most caught either the 19:27 fast or 19:50 slow coach....a trailing group of 4 who had some navigational problems finished a bit later also after a visit to the swimming, all in all... 22 with 10 swimmers and 2 paddlers...

  • 03-Aug-20

    And I stand corrected: It is perfectly possible to swim at high tide and low tide at Fairlight Glen. In fact at low tide the beach is transformed into a shallow sand beach. Only in between tides will you scrape your knees and stump your toes on the rocks ....

Length: Full walk: 26.2km (16.3 miles). Shorter options possible of Winchelsea to Three Oaks 12.9km (8 miles) or Winchelsea to Fairlight 20km (12.4 miles) - or Three Oaks to Hastings 13.3km (8.3 miles) T=3.316

9.34 Southeastern High Speed train from St Pancras International, changing at Ashford (arrive 10.11, depart 10.24) for Winchelsea, arriving 10.50. Change as quickly as possible at Ashford, as the Winchelsea train is only two-car and can get very crowded.

Late start option: 12.37 South Eastern High Speed train from St Pancras International, changing at Ashford (arrive 13.14, depart 13.24) for Three Oaks, arrive 13.57: you need to be in the front carriage for Three Oaks. Join the main group there at lunch (they should reach the pub at around 1.45) and do the 8.3 mile afternoon and evening part of the walk.

Buy a day return to Hastings, valid for Southeastern High Speed

This is a NEW NEW NEW route, not the same as the traditional Rye or Winchelsea to Hastings walk, though it has the same finish over the cliffs as that walk, and it borrows the alternative Winchelsea to Icklesham start from it.

Otherwise it follows an interesting inland route, over gentle hills and with fine views, before turning south and approaching the high ridge that forms the Hastings cliffs from behind - very attractive territory. In all this it cannot make any huge claims to originality because for most of its length it follows first the 1066 Walk route and then the 1066 Walk Hastings Link. But it departs from the latter to climb up to Fairlight, and then follows the coastal route (with its hills and dips) into Hastings.

This walk is intended to be a map-led/GPX walk - GPX file here and map here - but there are some written directions here - notes on the route, if you like, to be used in conjunction with a map or GPX. They may, for all I know, be sufficient to complete the walk without a map or GPX, but I can't guarantee it.

The intention is that lunch should be had at the quirky Three Oaks Inn (its website says it serves food all afternoon), 8 miles into the walk, but it might be hard to resist the wonderful Queen's Head in Icklesham, which is only 3.3 miles in. If you want to do the short 8 mile walk, you could lunch here, have tea at the Three Oaks, and then get the train from the adjacent Three Oaks station, from where trains depart at 16.36, 18.36 and 20.36 for Ashford and then the High Speed. If you are set on doing this option you need only buy a day return to Three Oaks.

Otherwise, 4.3 miles further on from Three Oaks brings you to Fairlight. The Coastguards Tea Room is, as far as I know, still operating here (it was up for sale last year, but its website is still there, so cross fingers it is still open: the website says its hours are until 6pm). This is not just a nice place for tea but you can also, if you wish, get a bus from Fairlight into Hastings at 16.35, 17.35 and 18.35, thus ending the walk after 12.4 miles.

Or fortified by tea and cakes, the last four miles of the walk are the familiar coastal route into Hastings, a series of three big dips and climbs, except that the closure of the path into Ecclesbourne Glen eliminates the last dip if you follow the official diversion (as the GPX does), and the first dip can be avoided by a short cut. In the second of the dips, if anyone has the energy, a swim may be possible at Fairlight Glen, depending on the state of the path (which is officially closed, but is rebuilt each year by the naturists who use this beach).

You end in the Old Town of Hastings, which has lots of refreshment and food options.

Trains back from Hastings are at 26 past the hour (until 22.26) via Ashford, changing to the High Speed and taking 1 hour 28 minutes. Or at 18 and 50 minutes past the hour to Charing Cross until 18.50 and then 19.50, 20.50 and 21.50 (1 hour 44 minutes).
  • 28-Jun-19

    Just to point out that the forecast temperature for Winchelsea tomorrow is 27 degrees - so a good deal lower than inland

  • 29-Jun-19

    The route basically follows the 1066 Country Walk, and its Hastings Link, with a start familiar from another Winchelsea walk, followed by a new routing from Icklesham along a low ridge to the south of the Brede valley, with fine views across the marshes, some vineyards, another low ridge to the north, and - occasionally - the sea to the south. It was hot so progress was maybe a bit slower than it might have been in normal weather and we took nearly 3 hours to the lunch pub, which is trad but nice, with large portions.

    From Three Oaks to Fairlight and the Three Glens we followed an interesting route, plenty of up and down, fine vistas (Camber and Dungeness), some nice woods but also some pretty overgrown stretches.

    At Fairlight some took a right turn for an unofficial shortcut, but about half of my sub-group walked the shown route past the coastguard station. We then lost plenty people to the beach in the second glen and others to Fish & Chips or a drink in Hastings, so only a few made the 17.50 train.

    15 had gotten off the posted train and at the lunch pub we met one who had arrived at Three Oaks via Hastings as he had planned, due to a late night out; plus one other who had been on the posted train from London (which was full and standing) but had failed to get on the connecting train at Ashford (which was full and standing and dozens still standing on the platform). Southern even put on a free Express Bus to Rye for the overspill people... So she took the next train to Three Oaks and met us there. 17

  • 29-Jun-19

    Only three of us went to The Coastguard’s tea room in Fairlight then? Gorgeous cakes, and a nice breeze on its open veranda. We then went to Fairlight Cove, where two of us picked our way over the boulders, exposed and underwater, suffering only a few cuts and grazes, to have a delicious swim in the not too cold sea. A lovely golden walk to Hastings. Still waiting to see what train we get home.

    Today’s butterfly was the Meadow Brown. I must have seen several hundred of them. Also lots of very hot sheep, some of them doubtless glad of their recent haircut.

  • 30-Jun-19

    7 went swimming in the cove. We got split up choosing a pub in Hastings but eventually 8 of us reunited on the 1950 back to London.