Before the Norman Conquest, Macclesfield was held by Edwin, Earl of Mercia, who also held much of the east of the county.
Three crosses survive from this period, originally located in Sutton, and J. D. Bu'Lock speculates that there might have been a Pre-Conquest church.
The area was devastated by the Normans in 1070, and had not recovered by 1086; the Domesday Book records the manor as having fallen in value from £8 to 20 shillings.
Hugh d'Avranches, Earl of Chester held the manor himself after the Conquest; there was a mill, meadow for oxen, and woodland 6 leagues by 4 leagues.
A Norman castle was built at Macclesfield.
Macclesfield was granted a borough charter by Ranulf de Blondeville, Earl of Chester, in the early 13th century, and in 1261 a second charter was granted by the future King Edward I, allowing a market, fair and judicial court.
The medieval town stood on the hilltop, centred on the parish church of All Saints, which was built in 1278, an extension of a chapel built in approximately 1220.
In 1357, a hall was built in the town for the mayor's court and the borough court (portmote).
The town lacked industries at this date and was described as poor, remaining a small market town until the end of the 15th century, with a population numbered in the hundreds.

The borough had a weekly market and two annual fairs: the Barnaby fair on St Barnabas day (11 June), the other on the feast of All Souls (2 November).
In recent years the Barnaby fair has been reinvented as the Barnaby Festival, a cultural festival in mid-June.
The weekly market no longer happens but on the last Sunday of each month the Treacle Market is held, a large market selling locally produced food and handmade items such as clothing, handmade goods and pottery.

Macclesfield was the administrative centre of the Hundred of Macclesfield, which occupied most of east Cheshire.
The Earl of Chester's manor of Macclesfield was very large, and its boundary extended to Disley.
The manor house was on the edge of the deer park, on the west of the town.
In the 14th century, it had a king's chamber and a queeen's hall, as well as a large stable, and the manor served as a stud farm for Edward the Black Prince.
The Earls of Chester established the Forest of Macclesfield, which was much larger than its present-day namesake.
It was used for hunting deer and pasturing sheep and cattle.
By the end of the 13th century, large areas of the forest had been ploughed because of the pressure of population growth.
In 1356, two trees from the forest were given to archer William Jauderell to repair his home.

Macclesfield Castle was a fortified town house built by John de Macclesfield in the later Middle Ages.
Construction began in 1398, and that year an application was made for a licence to crenellate, or fortify, the building.
Two chantries were founded in the town: one in 1422 by the Legh family, and one in 1504 by Thomas Savage.
In 1502, Macclesfield Grammar School was founded by Sir John Percyvale.

No proof exists that Macclesfield was ever a walled town.
When the settlement was first established and for some centuries afterwards there would have certainly been some sort of ditch and palisade round the western side of the town which was not naturally defended.
 This was necessary in order to keep out undesirable people and stray animals.
 No physical trace of a ditch remains though measurements and the shape of certain streets suggest where such a ditch could have been and most of the medieval building were within this area.
 It is unlikely that the ditch and palisade were succeeded by a wall for no record has been found of a murage tax, which would certainly have been levied to keep the wall in repair.
 The suffix "Gate" in the names of several Macclesfield streets has been taken to indicate the former presence of a gate in the sense of a guarded opening in a wall, however, this is very unlikely as the term 'gate' is derived from 'gata', Scandinavian for road, which became gate in Middle English.
Therefore, Chester Gate, the Jordan Gate and the Church Wall Gate (some sources
Before the Norman Conquest, Macclesfield was held by Edwin, Earl of Mercia, who also held much of the east of the county. Three crosses survive from this period, originally located in Sutton, and J. D. Bu'Lock speculates that there might have been a Pre-Conquest church. The area was devastated by the Normans in 1070, and had not recovered by 1086; the Domesday Book records the manor as having fallen in value from £8 to 20 shillings. Hugh d'Avranches, Earl of Chester held the manor himself after the Conquest; there was a mill, meadow for oxen, and woodland 6 leagues by 4 leagues. A Norman castle was built at Macclesfield. Macclesfield was granted a borough charter by Ranulf de Blondeville, Earl of Chester, in the early 13th century, and in 1261 a second charter was granted by the future King Edward I, allowing a market, fair and judicial court. The medieval town stood on the hilltop, centred on the parish church of All Saints, which was built in 1278, an extension of a chapel built in approximately 1220. In 1357, a hall was built in the town for the mayor's court and the borough court (portmote). The town lacked industries at this date and was described as poor, remaining a small market town until the end of the 15th century, with a population numbered in the hundreds.
The borough had a weekly market and two annual fairs: the Barnaby fair on St Barnabas day (11 June), the other on the feast of All Souls (2 November). In recent years the Barnaby fair has been reinvented as the Barnaby Festival, a cultural festival in mid-June. The weekly market no longer happens but on the last Sunday of each month the Treacle Market is held, a large market selling locally produced food and handmade items such as clothing, handmade goods and pottery.
Macclesfield was the administrative centre of the Hundred of Macclesfield, which occupied most of east Cheshire. The Earl of Chester's manor of Macclesfield was very large, and its boundary extended to Disley. The manor house was on the edge of the deer park, on the west of the town. In the 14th century, it had a king's chamber and a queeen's hall, as well as a large stable, and the manor served as a stud farm for Edward the Black Prince. The Earls of Chester established the Forest of Macclesfield, which was much larger than its present-day namesake. It was used for hunting deer and pasturing sheep and cattle. By the end of the 13th century, large areas of the forest had been ploughed because of the pressure of population growth. In 1356, two trees from the forest were given to archer William Jauderell to repair his home.
Macclesfield Castle was a fortified town house built by John de Macclesfield in the later Middle Ages. Construction began in 1398, and that year an application was made for a licence to crenellate, or fortify, the building. Two chantries were founded in the town: one in 1422 by the Legh family, and one in 1504 by Thomas Savage. In 1502, Macclesfield Grammar School was founded by Sir John Percyvale.
No proof exists that Macclesfield was ever a walled town. When the settlement was first established and for some centuries afterwards there would have certainly been some sort of ditch and palisade round the western side of the town which was not naturally defended.  This was necessary in order to keep out undesirable people and stray animals.  No physical trace of a ditch remains though measurements and the shape of certain streets suggest where such a ditch could have been and most of the medieval building were within this area.  It is unlikely that the ditch and palisade were succeeded by a wall for no record has been found of a murage tax, which would certainly have been levied to keep the wall in repair.  The suffix "Gate" in the names of several Macclesfield streets has been taken to indicate the former presence of a gate in the sense of a guarded opening in a wall, however, this is very unlikely as the term 'gate' is derived from 'gata', Scandinavian for road, which became gate in Middle English. Therefore, Chester Gate, the Jordan Gate and the Church Wall Gate (some sources
Macclesfield