Long a borderland, because of its location between the Boyne and the Cooley Mountians, Louth featured strongly in the struggles between the Gaelic Irish and the colonising English throughout the Middle Ages, with many records of towns plundered and burned and populations massacred. Most of Louth was in the Pale and so under direct English rule. Even the church was partitioned between the English and Irish (all Catholics), with the English-appointed Archbishop of Armagh forced to administer his see from Drogheda or Termonfeckin, as it was too dangerous for him to go to Armagh. Edward de Bruce, brother of the more famous Scottish king, Robert, crowned himself king of Ireland in Dundalk on the second of May 1316 and died nearby, just two and a half years later, at the Battle of Faughart (14th October 1318). He also burned the parish church of (English) Ardee with the whole congregation in it.
The O'Neills had a very strong connection with Dundalk and surrounding areas (including the Gap of the North) in the sixteenth century and Hugh O'Neill surrendered to the English at Mellifont in 1603. Later in the seventeenth century Drogheda survived a siege by the Ulster Gaelic army from 1641 to 1642. It was not so lucky seven years later in 1649, when Cromwell had a disastrous impact on the town, which wisely surrendered quietly after the Battle of the Boyne in 1690. After the battle William of Orange presented the Drogheda Corporation with a very fine mace, to replace that melted down by (his uncle and father-in-law) James II to make silver bullion to pay his bills. The Mace was restored in 2009/10 and placed on display in the town's Municipal Art Gallery, the Highlanes.