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Pittenweem is the number one port in the East Neuk of Fife and visitors will see the harbor at its liveliest when the fish sales are held early in the morning. The name Pittenweem means " place of the cave " and dates back to the very early days when a cave in old Cove Wynd was used as a place of worship by the missionary St. Fillan during the 7th century.

This cave was restored in 1935 and is still open to visitors. Inside there is the Saint Well and an altar where St. Fillan used to write - reputedly aided by a luminous glow from his left arm.

Lying of the shores of the East Neuk is the Isle of May where David I founded a priory about 1143. In the 14th century the priory came under the jurisdiction of the Augustinian monks of St. Andrews. This resulted in the priory being resited in Pittenweem which offered better protection from invading pirates. The new location was a boon for Pittenweem which soon became one of the most prosperous burghs in all of Scotland. The fishing industry naturally developed around the harbor whereas the trading centered around Market Square and the High Street, located at the top of the steep slopes rising from the shore.

The two centers were connected by various wynds ( alleyways ) such as Cove Wynd, Water Wynd and School Wynd and are the most interesting way to explore the character of the old village.

In 1541 the village became a Royal Burgh and soon after the Parish Church and Tolbooth were built in 1588. The Council Chambers were situated at the first floor level in the Tolbooth Tower and down below were the dungeons. In the distant past the folk of Pittenweem had a fearsome reputation for witch hunting and many a poor victim was thrown into the dungeons before being killed for dabbling in witchcraft. In the year 1704 Janet Cornfoot was the last witch to be cruelly killed in Pittenweem.

Pittenweem is ideally located for easy trips to St Andrews, Dunfermline, Culross, Perth, Edinburgh, Falkland Palace, and all of historic Fife.