Plantation Before the
Plantation of Ulster, the area covered by the town was known as
Killechally,
Killycolly and
Killycollie ( 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 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. 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. On 9 July 1921 the Free State barracks in Bailieboro were attacked and taken, the arms of its garrison being seized. ==Schools==