Built in 1565 by John Maxwell, the tower takes its name from an inscription Repentance carved on the stonework above the entrance door.

[4] Walter Scott made a note of traditions connected with the tower in Minstrelsy of the Scottish Border.

He knew the tower and the views from Trailtrow Hill very well,[6] leaving vivid descriptions in his letters and Reminiscences.

[1] Gun loops, shot holes and small windows are present with the entrance at the first floor level, now provided with a set of stone steps although originally a retractable wooden ladder would have been used.

[7] In 1579 Lord Herries wrote to James VI saying "..the wache toure upoun Trailtrow callit Repentance mon be mendit of the litill diffacing the Englische army maid of it.

The tower had only one small fireplace and was not designed as a habitation,[1] its purpose being to provide an elevated place of safety from which sentinels or guards could keep watch on the surrounding land, the West March of the Border, and the Solway Firth for English invaders or raiding parties.

A platoon of the Annan Home Guard occupied the tower with instructions to keep watch on the Solway for enemy invasion forces.

[8] Several suggestions regarding the origin of the name 'Repentance Tower' have been made in addition to the recompense for robbing the stone from Trailtrow Chapel.