Pitlessie Fair is an 1804 genre painting by the Scottish artist David Wilkie.

[1][2] It depicts the annual mayfair being held in his native village of Pitlessie, in Fife.

One of his earliest works, it came two years before his major breakthrough at the Royal Academy's Summer Exhibition in 1806 with The Village Politicians.

Both paintings show the strong influence that seventeenth century old masters had on Wilkie's work.

The success of Pitlessie Fair enabled Wilkie to move to London where he based himself for the rest of his career.