[3] The town is believed to have grown around the site of Cupar Castle, which was the seat of the sheriff and was owned by the earls of Fife.

[5] Towards the latter stages of the 13th century, the burgh became the site of an assembly of the three estates – clergy, nobility and burgesses – organised by Alexander III in 1276 as a predecessor of the Parliament of Scotland.

[5] Although written information of a charter for the modern town was lost, evidence suggested that this existed as one of the many properties owned by the Earls of Fife by 1294.

[6] The oldest document, referring to the royal burgh, was a grant by Robert II in 1381 to give a port at Guardbridge on the River Eden to help boost trade with Flanders.

[8] The Cupar area supports three multi-member wards with eleven councillors sitting on the committee of Fife Council.

[9] County Buildings on Catherine Street are the main headquarters for the east region of Fife Council, which deals with administrative, planning and agricultural issues.

[10] Cupar is in the UK Parliamentary constituency of North East Fife, electing one Member of Parliament (MP) to the House of Commons by the first past the post system.

[18] Reported places of birth were:[13] The economic activity of residents aged 16–74 was 42.20% in full-time employment, 12.32% in part-time employment, 5.89% self-employed, 3.10% unemployed, 2.96% students with jobs, 3.94% students without jobs, 17.68% retired, 4.83% looking after home or family, 4.35% permanently sick or disabled, and 2.72% economically inactive for other reasons.

To the east is St Catherine Street, home to the burgh chambers and county buildings, both designed by Robert Hutchison.

[7] The Category B listed[21] Cupar Burgh Chambers, built between 1815 and 1817, contains a three-story bow street corner and a doric entrance.

[7] At the east end of St Catherine Street is the Category B-listed[24] Cupar War Memorial in a classical Greek style overlooking the Cart Haugh, one of several designed by John Kinross with assistance from leading contemporary sculptors, for the exception of the Victory statue which was done by Henry Snell Gamley.

[7] On the Bonnygate, the Category A-listed[26] Preston Lodge built by the Laird of Airdrie is the town's second oldest building.

On the Kirkgate is the Parish Church of Cupar Old and St Michael of Tarvit, designed by the architect, Hay Bell.

[7][31] To the south of the town on the A914 and A916 is the Category A-listed[32] Hill of Tarvit mansion house and nearby scheduled monument[33] Scotstarvit Tower.

The larger employers are Kettle Produce (fruit and vegetable producer) and Fishers Services Ltd. Other employers include the SRUC Campus at Elmwood College (Fife education); Quaker Oats Ltd (food and drink) and Fisher & Donaldson (food and drink).

The main shopping facilities are located between the Bonnygate and Crossgate, including family-owned businesses and some smaller chain stores.

Shops include Burger King, Costa Coffee, B&M, Card Factory, Indigo Sun, Baynes the Baker and Nimbus Beds.

[46] Westfield Family Nurture Centre was opened in 1981 as part of Castlehill Primary School, but was made independent at some point.

[47] Castlehill Primary School opened to pupils on the present site in 1975 and is located on the town's outskirts and has enrollment of 420.

[50] Bell Baxter High School located on Carslogie Road, serves both the town and surrounding villages.

The station is situated on the East Coast Main Line, served by ScotRail and CrossCountry with regular services running between Edinburgh Waverley and Aberdeen.

The SNIY provides a Light Cavalry capability and have travelled to Germany and the United States on training and on operations in Afghanistan, Iraq and Cyprus.