Motte & Bailey
The motte and bailey castle played a significant role in the control of the Scottish-English border, guarding the area from invaders coming north from England. Edward I of England made several attempts to occupy Scotland during the Wars of Independence and in 1332 John Balliol, who had been put on the throne of Scotland by Edward II camped in the town of Annan, where he
was attacked before fleeing to Carlisle.
The fortified motte and bailey castle in Annan was the Bruces’ main stronghold
until 1218. It is likely that part of the castle embankment was eroded around this time. Legend tells that it fell victim to a curse placed on it by the Irish churchman St Malachy, who stayed with Robert the Bruce II in 1140. During his stay St Malachy is reputed to have overhead servants talking about a robber who was awaiting sentence and probable death. St Malachy asked Bruce to spare the life of the man. Bruce promised he would and in turn St Malachy blessed the Bruce household. Later as he was leaving, St Malachy saw the robber hanging from Annan’s gallows and angered by the deceit, put a curse on the household. The story goes that soon after, a flood swept away a large section of the motte bringing down part of the castle resulting in the Bruces transferring their headquarters to Lochmaben. Although the castle was abandoned, Annan continued to be important as a boundary post close to the Solway Firth. Indeed evidence of the town’s important defensive position right up until the Second World War can still be seen in the spigot mortar overlooking the bridge crossing the River Annan. 
The medieval roots of the town’s layout can be seen in the 1859 edition of the Ordnance Survey map.
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.
The Riding of the Marches in Annan.