In the early 17th century, William Bailie established Bailieborough. He was a planter from Ayrshire in Scotland. He built a castle beside a lake but nothing survives today, , to the west of Bailieborough there are forest trails through the estate. During the 1798 rising there was a battle at the Rebel Hill, which is a mile to the north-west of the town. Captain William Young bought the Bailieborough estate early in the 19th century. who had made a fortune in the East Indies. His son John was a member of parliament and governor general of Canada and New South Wales. The town has very close links with Canada; there is even a small region of Ontario called Bailieborough. In 1903 a co-operative was set up to market dairy products and this continues to bring prosperity to the town.
