This beautifully preserved medieval town on the East Sussex coast is really worth more than a daytrip – it’s a terrific place to spend a weekend! 

The history of this fortified township – which was once on the coast but now sits some two miles back from open water thanks to the silting up of the harbour – stretches back to at least Saxon times.

But it was in the Middle Ages that, thanks to its position relative to France, it flourished as a port and was eventually given the distinction of being a member of the Cinque Ports Federation (the federation originally included the ports of Hastings, New Romney, Hythe, Dover and Sandwich and was later expanded to include Rye and Winchelsea).

However, the proximity to France also meant the town had an interesting relationship with the French who conducted repeated raids including in 1339 when 52 houses and a mill were burned, and in 1377 when the town was almost completely burnt to the ground and the invaders made off with the bells of St Mary’s Church (dating from 1150, the church is certainly well worth a visit, particularly for the stunning views from the bell tower roof).

Key surviving fortifications including the 14th century The Ypres Tower (originally called Baddings Tower, this 40 foot high structure – pictured right – with three round towers is now home to half the Rye Castle Museum – the other half being in East Street) and Landgate (this was built as part of a series of walls and gates constructed after the devastating 1377 raid) were built to counter this threat and when the French raided again in 1449, they were successfully resisted.

Rye’s location – it now sits at the confluence of the Rother, Tillingham and Brede Rivers – also meant that since its earliest days, it was popular with smugglers despite government efforts to stop them (they did eventually succeed in the early 19th century thanks to customs law reforms and the establishment of a national coastguard service). Among the most famous to frequent the town was the Hawkhurst Gang, who used the Mermaid Inn in the beautiful cobbled Mermaid Street (pictured, below) as one of their bases in the area in the early 18th century (the gang was eventually captured and executed in 1749). The inn apparently may date back as far as the 12th century and has a fascinating history.

Aside from the many Tudor and Georgian homes, notable buildings include the Old Grammar School in High Street (founded in 1636), the Town Hall in Lion Street (1742) and the red brick fronted Lamb House in West Street – once home to authors Henry James and EF Benson and now owned by the National Trust. There’s also a model of the town (complete with sound and light show which gives a great overview of the town’s history) at the Rye Heritage Centre located in an old sail loft on Rye Strand Quay – a good place to visit for information and details of walks and tour options.

Not far from Rye can be seen Camber Castle, a round artillery fort (essentially a glorified gun platform) built by King Henry VIII. It’s now managed by English Heritage and can be visited on tours.

Rye is located about an hour’s journey by car from the M25 and can be reached by train from Charing Cross, London Bridge or Waterloo East or from St Pancras (via Ashford International).