The town's two historical points of interest are the ruined medieval Crowland Abbey and the 14th-century three-sided bridge, Trinity Bridge, which stands at its central point and used to be the confluence of three streams.
In about 701 a monk named Guthlac came to what was then an island in the Fens to live the life of a hermit. Following in Guthlac’s footsteps, a monastic community came into being here, which was dedicated to Saint Mary the Virgin, Saint Bartholomew and Saint Guthlac in the eighth century.
The place-name 'Crowland' is first attested circa 745 AD in the Vita S. Guthlaci auctore Felice, reprinted in the Memorials of Saint Guthlac published in Wisbech in 1881. Here the name appears as Cruglond, Crugland, Cruuulond and Cruwland. It appears as Croiland in the Domesday Book of 1086. The word cruw is thought to mean a bend, and to refer to the bend in the River Welland at Crowland, which was more pronounced before the draining of the fens.
The town of Crowland grew up round the abbey. By a charter dated 716, Æthelbald of Mercia granted the isle of Crowland, free from all secular services, to the abbey with a gift of money, and leave to build and enclose the town. The charter's privileges were confirmed by numerous other royal charters extending over a period of nearly 800 years. Under Abbot Ægelric the fens were tilled, the monastery grew rich, and the town increased in size, enormous tracts of land being held by the abbey at the Domesday Survey.
The Croyland Chronicle (1144–1486 ), an important source for medieval historians, is believed to be the work of some of the monastery's inhabitants.
The town was nearly destroyed by fire (1469–1476), but the abbey tenants were given money to rebuild it. By virtue of his office the abbot had a seat in parliament, but the town was never a parliamentary borough. Abbot Ralph Mershe in 1257 obtained a grant of a market every Wednesday, confirmed by Henry IV in 1421, but it was afterwards moved to Thorney. The annual fair of St Bartholomew, which originally lasted twelve days, was first mentioned in Henry III's confirmatory charter of 1227. The dissolution of the monastery in 1539 was fatal to the progress of the town, and it rapidly sank into the position of an unimportant village. The abbey lands were granted by Edward VI to Edward Clinton, 1st Earl of Lincoln, from whose family they passed in 1671 to the Orby family.
In 1642, near the start of the English Civil War, the remains of the abbey were fortified and garrisoned by Royalists under Governor Thomas Stiles. After a short siege it was taken by Parliamentarian forces under the command of Oliver Cromwell in May 1643.
The surrounding agricultural area suffered from extensive flooding in 1947 as the River Welland and the surrounding drain network was overwhelmed with meltwater. A flood defence bank, West Bank, still exists, forming the north-west perimeter of the village and eastern flank of the River Welland's flood plain.
The Great Northern and Great Eastern Joint Railway crossed the north-east part of the parish until the 1980s. It passed near De Key's Farm to the east and Martin's Farm to the north. Postland railway station was near Postland House.