Before the Norman Conquest, Macclesfield was held by Edwin, Earl of Mercia, and assessed at eight pounds. The Normans arrived in 1070 and devastated the area so thoroughly that the Domesday Book recorded the manor's value as having collapsed to twenty shillings. The medieval town rebuilt itself on the hilltop around what is now St Michael's Church, originally All Saints, and was granted its borough charter in 1261 by Edward, the future Edward I. Macclesfield Grammar School was founded in 1502 by Sir John Percyvale. The Cheshire archers, an elite body of longbowmen, served Edward I as personal bodyguards from 1277, and Cheshire bows fought at Crecy and Agincourt. From its hilltop core, the town spread down to the River Bollin and outward toward the moors, the boundaries of the Earl of Chester's manor reaching as far as Disley.

Macclesfield had a button industry from the seventeenth century, and by the middle of the eighteenth it was becoming the world's biggest producer of finished silk. The first water-powered mills were succeeded by steam, and the population grew from around 2,600 in 1664 to 8,743 in 1801 and 24,137 by 1841. Paradise Mill, built for silk throwing and Jacquard weaving, reopened in 1984 as a working museum where visitors can watch the looms run. The Macclesfield Canal, built between 1826 and 1831 to connect the town to Marple in the north and Kidsgrove in the south, was surveyed for its Act of Parliament by Thomas Telford himself. The mill town was, by local tradition, the only one in England to escape bombing in the Second World War, and after the war two pharmaceutical companies, Geigy (now Novartis) and ICI's pharmaceuticals division (now AstraZeneca), set up large facilities here. AstraZeneca remains a major employer.

Macclesfield's landmarks reward a walk. The Georgian Town Hall on Market Place was designed by Francis Goodwin and completed in 1823 on the site of the old guildhall. St Alban's Roman Catholic Church on Chester Road, Grade II* listed, was designed by Augustus Welby Northmore Pugin, the architect of the Houses of Parliament interiors. The Arighi Bianchi furniture store, founded in 1829, occupies an extravagant glass and iron building visible from the bypass. The 108 stone steps from Waters Green up to St Michael and All Angels Church are themselves a local landmark, the kind of climb that residents take in their stride and that visitors pause halfway up to photograph. The Sunday School on Roe Street, completed in 1812 for 1,127 boys and 1,324 girls, was an extraordinary feat of working-class education founded by John Whitaker in 1796 to, in his words, lessen the sum of human wretchedness.

For a town of about fifty-four thousand people, Macclesfield has produced a remarkable musical output. The British blues singer John Mayall was born here in 1933 and shaped the careers of Eric Clapton, Mick Fleetwood and Mick Taylor through his Bluesbreakers. Ian Curtis, lead singer of Joy Division, lived and died in Macclesfield, and is buried at Macclesfield Cemetery where his memorial draws visitors from around the world. Stephen Morris and Gillian Gilbert, who founded New Order with Joy Division's survivors after Curtis's death in 1980, are both from the town, and the 2007 film Control, about Curtis's life, was shot here. The Macc Lads, a band who sang foul-mouthed comic songs from the 1980s onward, were also locals, as was the Brit-Pop band Marion and, more recently, the rock band the Virginmarys. Silk Brass Band, the brass band tradition meeting the silk-town identity, has competed in the championship sections of the UK brass band system.

In 2004 a study in The Times named Macclesfield and its borough the most uncultured town in Britain, citing a thin offering of theatres and cinemas. The town has spent the years since arguing with that verdict. The Northern Chamber Orchestra, the oldest professional chamber ensemble in northwest England, is based at the Macclesfield Heritage Centre and presents eight concerts a year. The Macclesfield Literary and Philosophical Society was founded in 2006, partly as a direct response to the article. The Barnaby Festival, a reinvention of the medieval St Barnabas day fair, fills the streets every June. Cinemac and the Silk Screen art cinema operate in the Heritage Centre, two amateur dramatic societies stage productions in their own venues, and Gawsworth Old Hall hosts an annual Shakespeare festival just outside town. The 2008 happiness ranking by Sheffield and Manchester universities placed Macclesfield fifth out of 273 districts in Britain. The reading depends on the question.