Pittenweem
Pittenweem was founded as a fishing village around an early Christian religious settlement, it was granted the status of a Royal Burgh by King James V in 1541, giving it the right to self government and the right to trade with other countries in return for paying taxes to the crown. By 1587 Pittenween ranked as the twelfth richest town in Scotland.
Pittenweem has a deep, safe harbour with a covered fish market, it is the main harbour for the fishermen of the East Neuk of Fife. You will notice that the end of the buildings are "crow step [Scots: corbie-steppit] gable", where the gable ends rise in steps rather than the more normal smooth angled line - an architectural feature imported from Belgium and Holland.
The layout of Pittenweem town centre, was not to any plan, but grew up piecemeal over several centuries, its numerous winding streets and alleys is one of its particular charms. Few 
Scottish towns have so well preserved their ancient character.
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The Pittenweem Arts Festival started a number of years ago when a couple of people decided to exhibit paintings together for a few days. Gradually more and more people joined in the fabulous annual arts festival today. The ordinary house holders in Pittenweem turn over parts of their home to the artists for the festival. It is a really original way for art to be shown and you are guaranteed to have a great time. The festival
is held for 10 days from the first weekend in August each year.
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A short walk through Pittenweem to some of the points of interest.
1. The Mercat Cross, the symbol of the Pittenweem burgh's right to hold markets and fairs, stands at the east end of the High Street.
2. Kellie Lodging. In 1651 the town entertained King Charles II to a meal on his way to Anstruther. The meal was served in Pittenweem outside Kellie Lodging. Until recently it was known as King's Halt in recognition of this occasion. It was the town house of the Earls of Kellie.
3. The Pittenweem Tolbooth at the top of the High Street had a prison on the ground floor while the council chambers were on its upper floor.
4. St Fillan's Cave is in the heart of Pittenweem. Traditionally St Fillan lived and taught the Picts here during the 7thC. Obtain the key from the Cocoa Tree and Chocolate Shop, 9 High Street. Adults £1, (free leaflet), children free.
5. Gyles House was built in the 17thC for Captain James Cook who took Charles II to France after his defeat at the battle of Worcester in 1651.
6. Pittenweem harbour is home to 
one of Scotland's last remaining fishing fleets. The outer pier is the oldest, building probably started in the 16thC. The tower on the outer pier was built in 1864. A fish market is held most weekday mornings.
7. West Shore houses. Here the fishermen lived in homes much smaller than the sea captains' houses at East Shore, Pittenweem.