[3] On 2 January 1541, Pitlessie was created a free burgh of barony in favour of John, 4th Lord Lindsay by James V. The land was then passed through down his descendants until it was later sold to Crawford of Montquhanie.

[7] From its beginnings, the linen industry of the River Eden, along with the surrounding arable farmland, served as primary employers for the village's small populous.

Founded by James Martin of Priestfield, the maltings were acquired by the Bonthrone family in 1937 who operated similar facilities in Newton of Falkland, Ladybank, Stratheden, and Auchtermuchty.

Local issues in the village and wider parish are managed by the Cults Community Council, which meets on the first Monday of every second month in the Wilkie Memorial Hall.

[16] The Pitlessie Public Park was opened in 1900, on land gifted to the Parish Council by the Laird of Priestfield.

The school, along with Craigrothie Primary, is led by Tamsin Frost and is attended by a single class of under 20 pupils.

After returning from the Trustees' Academy in 1804, in one of his earliest works, he depicted the scenes of Pitlessie Fair which included many of his family members and neighbours.