At the heart of the town are the Bonnygate, and the adjoining Crossgate, which are the town's principal shopping streets.

At the meeting of the two stands the Mercat Cross, which dates from 1683 and was relocated from the Fluthers hill in 1897.

Notable buildings in the town include the Parish Church of Cupar Old & St Michael of Tarvit, St John's Church, the Fife County Buildings, Yeomanry House an old Napoleonic prison, now the Fife and Forfar Yeomanry/Scottish Horse barracks, and the A-listed Tarvit Home Farm Steading with its unusual and distinctive spire.

To the South by the village of Craigrothie are the Hill of Tarvit mansion house and Scotstarvit Tower. The house was rebuilt in 1906 by Sir Robert Lorimer in the Edwardian style to house a collection of French, Chippendale and vernacular furniture. Dutch paintings, Flemish tapestries, Chinese porcelain and other artworks are also on display.

There are plenty of activities for families to enjoy with Cairnie Fruit Farm offering you the chance to pick your own strawberries, raspberries and blackcurrants whilst your children can explore the six acre Mega Maze.

Cupar was established as a royal burgh in 1363 by David II of Scotland and was the location of the 11th and 12th century castles of the Macduffs, thanes of Fife, who featured in William Shakespeare's famous play Macbeth.