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Maybole and district had many associations with Robert Burns, whose birthplace at Alloway is 5 miles north of the town. Burns’ mother, Agnes . b Brown, was born in Kirkoswald Parish and lived for thirteen years in Maybole with her maternal grandmother before her marriage to William Burness.

They met for the first time at a fair in the town and the site of their meeting place is marked by a small bust of the Poet on the gable of a shop at the foot of Maybole High Street. Burns often visited Maybole to meet his old school friend William Niven who had been at school with him in Kirkoswald Village. This village is 4 miles south of Maybole and in the old graveyard there are buried the world famous drouthy cronies, Tam o’ Shanter and Soutar Johnnie.

Since 1193 when Duncan the first Earl of Carrick granted a charter of Maybole to the Monks of Melrose, through the centuries to the present time, the old town of Maybole has seen many changes. The Prince of Wales is the present Earl of Carrick and Minniebolers are ever proud and conscious of this fact.

Although religion ruled, as is evidenced by the many chapels throughout the district, at the same time there were warlike periods when the might was right and there are many old fortified castles, mostly built in true Scottish baronial style, scattered around Maybole and district. Some, such as Cassillis, Kilhenzie, Killochan, Maybole Castle. etc. are still inhabited and in good preservation, while only the ruins of many others remain.

Originally a quiet rural town built on a sloping hillside overlooking the Southern Uplands, gradually Maybole through the centuries grew until in the 19th century it was a thriving weaving town of over 6,000 inhabitants and was also a busy market town for the farmers from the surrounding country. In coaching days, before railways, Maybole was the "half way house" between Glasgow and Port Patrick, the port for Ireland, and all travellers rested a night in the town. Many travelers such as Keats, Wordsworth, Shelley, R. L. Stevenson and others stayed over to explore the wonderful countryside and to write about it.

At this time the famous road maker McAdam lived in the district and carried out his experiments on the local roads and the first macadamised road ever laid is traditionally said to be at Whitefaulds Farm, in Culzean Road, Maybole.

Gradually weaving died out through the introduction of power looms in larger towns and boot and shoemaking became the town's main industry. This has also receded and efforts are now being made to attract new industry to the town.