The Town of Whitstable grew from the main road to Canterbury, now known as the high street, and the alley ways developed as local residents needed greater access to the sea. The multitude of alleys also served as convenient escape routes for smugglers, as Whitstable was, like most Kentish coastal towns, awash with the illegal trade in tobacco and spirits, as well as people during the Napoleonic wars.

Once known as Granny Bell's Alley, due to the fact that a grandmother of sixteen children lived there, the reason for its present title quickly becomes clear as you try to pass through it! The walls on each side loom high and dark as the alley bottle-knecks at the Island Wall end. According to history, the alley way may also have got its name from a game local boys once played with a potentially very unamused overweight policeman who was unable to pursue them through this confined space.

Once upon a time, various Whitstable pubs, regardless of the law, would take possesion of nerby stretches of land in order to provide their patrons with safe passage to and from their establishment. This alley was one such example, however, today it is the site of "The Old Favourite", an oyster yawl built over a hundred years ago for the oyster trade. It now serves as a traditional exhibit, and has recently received the care and attention needed to return this beautiful example to its former glory.

Here's where the coastguards built their quarters in an attempt to combat Whitstable's once thriving smuggling trade.

In the great freeze of 1895, dozens of children would use this alley every morning to go to Mr.Collar's store where food, cocoa, and warmth were supplied free of charge. It was also once the site of a saw pit where planks would be cut for boats' timbers.

This slipway once served as the approach route for horses to sailing ships lying off shore. The horses could paddle up to the flat-bottomed Thames barges which would sit on the sea bed at low tide. Oysters and iron pirates produced in Whitstable would be loaded here. The name may have been different in the past though, as apparently, a local pub called "The Bear and Key" may be a pointer to an older name - "The Baron's Quay", named after a local lord of the manor.