Motte & Bailey
Annan’s position close to the border and the disputed lands between Scotland and England made it a target for reivers. Watch towers were positioned on high points around the town in the 16th century, and the remains of many, such as Repentance Tower, can still be seen.
The motte and bailey defending the river crossing provides significant evidence of early medieval Annan. As the settlement expanded in later medieval times it followed the line of the present-day High Street. Although there are no extant medieval buildings from this period, evidence of the town’s medieval layout with its once long burgage plots running back from the main street, can still be seen in some of the wynds and courts, such as Downie’s Wynd. In 1296 Annan had become a burgh but when the town was attacked and burned by the English in 1516, the charter was lost. Two decades later in 1538 James V reinstated Annan as a royal burgh and in 1612 James VI reconfirmed the town’s royal burgh status.
This gave Annan important trading privileges, including rights to fish the river, and the town developed to have a busy market and later a port. Today areas such as Fish Cross, which marks the site of the old fish market, testify to the town’s medieval past.