A railway town in the Howe of Fife, lying to the north of the River Eden and 5 miles (8 km) southwest of Cupar.

Ladybank developed during the latter half of the 19th Century at a railway junction built on land drained during the 18th century and formerly known as the Moss of Monegae or Our Lady's Bog. Lady's Bog was changed to the more elegant Ladybank and the name Monkstown which is applied to the southern quarter of the town is the only part of the settlement that predates the building of the railway in the 1850s. It is a reminder of the days when the monks of Lindores Abbey used to cut peat here.

The town was designated a burgh in 1878 and developed linen and maltings industries. Ladybank Railway Station is reckoned to be one of the oldest unaltered stations in Scotland. There are forest walks in the neighbouring Heatherhall Wood. Sand and gravel are extracted at Melville Gates. At Annsmuir, a half-mile (1 km) to the northeast, was a prisoner-of-war camp built in 1942. It is now the location for a caravan park and the 18-hole Ladybank Golf Course.

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