Plantation

Before the Plantation of Ulster, the area covered by the town was known as Killechally, Killycolly and Killycollie (Irish: Coill an Chollaigh^[2]). The modern town was founded by William Bailie, a Scottish planter who was granted the lands of Tonergie (Tandragee) in East Breifne by James I, the King of England. This area was known as the Barony of Clankee, later known as Bailieburrow.

The conditions of being granted these lands were that within 2 years Bailie had to have constructed a house and bawn for himself, along with building tenant houses so he could collect revenue in the form of rent. An annuity would have to be paid to the English monarch, this annuity would also be reduced if Bailie gave preference to settling Scottish people on his land. Included in his duties of planting the area, he had to ensure that there were blunderbusses and muskets available so he could arm his men to defend the new plantation. Finally, he was obliged to take an Oath of supremacy to the English monarch as the Supreme Governor of the Church of England and the undisputed English monarch.

By 1613, Bailie had constructed an estate house for himself known as 'Manor of Bailieburrow'. This house, later known as Bailieborough Castle, was situated in a demesne that is today known as Castle Lake Forest. (This house was damaged by fire in the early 20th century and demolished in the 1930s.)^[5]

The town continued to develop, and in 1626 a report recorded that the town's name was now Bailieborough, which it has maintained to this day. Originally, a number of thatched houses had developed around the gates of the castle but this was deemed unsightly and it was decided that the settlement would be moved. Thus, Bailieborough moved to where the current old Church of Ireland chapel is located in the town. This remains the town's location.

In 1685, ownership of the estate was passed to a Scottish man known as Hamilton, who then sold the estate to a man called Colonel Stewart. The estate changed hands again when it was sold to Stewart Corry, a landowner from Rockcorry and a member of the Corry family. Leading up to the 1798 Rebellion, the castle grounds were used for training by rebels. Today, a memorial to the rebels stands at the foot of 'Rebel Hill' in the castle grounds. In 1814, the estate was sold to Sir William Young who had returned from travels in the East Indies. Young is responsible for the current design of the town, with the Main Street design being attributed to him.

Later development

Bailieborough's main street

The 1800s saw additional development in the town. For example, the town's courthouse was erected in 1817, with the Bridewell Jail being opened in 1833. The courthouse is no longer in use for its original design and is now a community hall. In 1833, work began on a new Church of Ireland church located at the bottom of the town. It was completed in 1875 when the bell was erected in the Belfry. The church replaced the old Protestant church located in the estate of Woodview, which now lies in ruin. As of 2023, the incumbent rector is Canon Ian W. Horner, having served in the role since 2016. In 2023, he also became Archdeacon of Kilmore.^[6][7]

A new Catholic church was constructed in 1839, with Phillip O'Reilly as the parish priest at the time. It replaced an old thatched chapel that had stood since the 1700s. The bell tower was constructed in 1851, while between 1868 and 1870 the chancel, baptistery and sacristy were erected. The marble altar located in the church has been in the church since 24 December 1895. The Stations of the Cross inside the church were painted by George Collie, an Irish artist in 1956.^[5] As of 2023, the parish priest was Fr. Ultan McGoohan, who moved from Teemore in 2019.^[8]

On 9 July 1921 the Free State barracks in Bailieboro were attacked and taken, the arms of its garrison being seized. ^[9]