Winchelsea Loop

Winchelsea Loop

by Graham Buckton 

Broadbridge Heath, West Sussex

Graham only passed his test in August 2022 but since getting through his mod 1 & 2 at the first hurdle, he's really 'hit the ground running'.

He'd long since considered getting in to biking and after reading a review of an electric bike he immediately booked a taster session. He must have enjoyed himself as it was only a couple of months later that he had his A licence, after passing on a Kawasaki 650Z (green of course).

So started the hunt for his first bike. He wanted something to hone his skills he says  it had to be, "compact, light and nippy".  He came across a 2nd hand BMW310, single cylinder, light, loads of MPG and with a seat height that Graham was comfortable with. 

Graham on board his BMW

Graham's Route

Starting from The Chalet, a small but popular bikers café just south of Cowfold in Sussex.  We will head south and east into the South Downs National Park before entering the High Weald Area of Outstanding Natural Beauty (ANOB). There are many places of interest along or near the route. Whilst some of these will be pointed out the object of this run is to visit wonderful Winchelsea. It is reputed to be the smallest town in Britain but it has lots to offer as we'll see later.

The route is roughly a loop and ends in East Grinstead high street. Clearly as it is a loop it can be accessed from any point. 

So what makes this ride so special?

"Immediately after turning right out of The Chalet, you are on some special roads. there will be a really good mix of quaint villages, winding roads with enough national speed limit signs to make it interesting"

The route heads towards the County town of East Sussex, Lewes. But not via the normal route and one far more interesting and surprisingly quick. I'd recommend getting off the bike in historic Ditchling where there is a lovely cafe near the crossroads named The Nutmeg Tree. The café is styled on the 30's and 40's and staff are dressed accordingly with that time. Also from the village you could detour to Ditchling Beacon, which from the car park at the top the view is sensational. On leaving the village you'll head towards Plumpton on the B2116. This road is  a stunner, it follows the line of The South Downs until it reaches A275 on the outskirts of Lewes.

Castles & Cafés

This route skirts Lewes, if you've never visited the town I would highly recommend it, though you'll need at least half a today we'll ride through.

Graham's run continues to journey east on roads running parallel to the busy A27 and A259 coast roads. We'll ride through Ringmer without much of a 2nd look, Lower Dicker will grab our attention but Herstmonceux is certainly worth some attention. The impressive 15th century Herstmonceux Castle is the former home of The Royal Observatory. 

Our next point of interest is the town of Battle. The site of The Battle of Hastings 1066 when England fell to its Norman invaders. William (The Conqueror) ordered an Abbey to be built on the site. This today it is run by English Heritage. The attractive main street has many shops, cafes, banks and pubs.

Detour to Hastings

Leaving Battle, Graham's route goes around Hastings, though I would certainly say it is worth the detour. If you head there, make your way down the eastern end of its seafront. There you'll enter Old Hastings. The beachfront here is residence for the largest beach launched fishing fleet in Europe. You'll also see huge beach huts, they are in fact used to hang and dry fishing nets.

Hastings Old Town is a must for all visitors. There are ancient churches and lots of passages and narrow streets (twittens) to explore. One of the oldest buildings, the Court House, which stands at the southern end of The Bourne, was built around 1450.

Some of the best streets to visit in the Old Town are George Street, High Street and All Saints Street. Steeped in history these streets are also great for shopping, restaurants and bars.

Don't forget to visit Hastings East Cliff funicular railway. The top is the gateway to Hastings Country Park.

Pett Level and the Royal Military Canal

The Royal Military Canal is a canal, built at the start of the 19th century, that runs for 28 miles  between Seabrook near Folkestone and Pett Level. It was constructed as a defence against the possible invasion of England during the Napoleonic Wars. Park up at the Pett Level car park and you'll be able to marvel at one end of this incredible feat of engineering. Feeling energetic? You can walk its length quite easily.

Pett Level is a great place to take a look at one end of The Royal Military Canal


Following a short ride along the coastal road, you'll take a left turn and enter the town of Winchelsea through Strand Gate.

Park wherever you can, close to St. Thomas' Church and explore the town.

Winchelsea was once an important trading port. Though then the town was situated at the foot of Iham Hill where it stands today. "Old" Winchelsea which was located on a shingle promontory was devastated by severe storms in 1287. Destruction led to the new fortified town we see today being built on safer ground. This town had to withstand not only attacks from the sea, but attacks from our neighbours across the sea. It's commanding position, fortifications and streets laid in a block system all helped it not just survive, but the town thrived and became one of the primary ports of the realm. Shipping, shipbuilding, fishing, travel and trade, with some wrecking and piracy thrown in, all contributed to the common good - but the good times were not to last...Black Death, French and Spanish raids all reduced the population. As if that all wasn't enough, the harbour on which Winchelsea's prosperity depended, silted up and became unavailable.

Town Highlights

The Court Hall Museum  (admission £3) Displays and exhibits that illustrate the history of the town

St Thomas's Church originally a church of cathedral proportions. French and Spanish raids during the Hundred Years' War left it severely damaged.

In the graveyard you will find the burial place of Spike Milligan You'll discover for yourself whether the headstone is in fact inscribed with the words, "I told you I was ill".

Wesley's Tree stands in German Street with a plaque commemorating John Wesley's last open air sermon preached in 1790.

Further reading:

We'll now head towards home and the finish point in East Grinstead High Street. There is unlikely to be much time left to get off your bike, but Graham has pointed out a few places well worth further investigation.

Scotney Castle, owned and managed by the National Trust. A wonderful house, the ruins of the castle, wonderful gardens and café.

Also nearby Bewl Water. Busy leisure facility with café and toilets.