George and Mary Johnston were the first permanent settlers in Islington. They made the arduous journey from Pennsylvania to Upper Canada in 1798, and around 1808 settled in Islington. Initially, they lived with their nine children in a log cabin they built on a 100-acre Clergy Reserve lot, which straddled Dundas between Kipling Avenue and approximately where Mabelle Avenue is today. Three of their sons, Thomas, Henry, and William, served in the 3rd York Militia during the War of 1812 and survived unscathed. In 1815, the Johnstons purchased an another 100-acre lot on the west side of Kipling Avenue, between Bloor Street and Burnhamthorpe Road, and moved into a new stucco-over-frame house they built at the north end of the property. Eventually six generations of Johnstons lived on and farmed the Kipling property, with the last piece of their land sold out of the family in 1985. Four heritage Johnston houses, built between 1862 and 1903, still stand in Islington at 1056, 1078 and 1100 Kipling Avenue and 66 Burnhamthorpe Road.
Other important early settlers in Islington were Amasa and Desdemona Wilcox, who arrived from New York State with their family about 1815. In 1816 they leased the Clergy Reserve lot immediately north of the Johnstons, which straddled Dundas between Mabelle and Islington Avenues. Around 1820, Amasa built a saw mill on Mimico Creek, half a mile north of Dundas, in what is now Islington Golf Course, operating it with his second son, Friend. About 1830, Amasa’s eldest son, Truman, built the first general store in Islington on the north side of Dundas, between Burnhamthorpe Crescent and Mimico Creek, where Second Cup is today. Amasa moved to Oxford County in 1839, but he retained ownership of land in Islington until his death in 1870 and generously donated adjacent lots on Dundas, west of Burnhamthorpe, for the village’s first three key institutions: a school in 1832, a Methodist church in 1834, and a non-sectarian cemetery ca. 1844.
In 1830, Thomas and Margaret Montgomery leased 200 acres of Clergy Reserve land between Islington Avenue and Royal York Road, running south from Dundas to Bloor Street. They built a large Inn of stone from the Mimico Creek valley, adding exterior stucco and two wings in 1838. In the 1840s, they expanded their property to 400 acres. The Inn operated until about 1856, but the family continued to farm their large property using hired farm superintendents. The portion of the property around the Inn remained in the family, operated by tenant farmers, until 1946 when it was sold to a Presbyterian church. In 1960, it was purchased by developer, Louis Mayzel, who planned to replace it with a strip mall. The Etobicoke Historical Society convinced Mayzell to save the Inn and sell them the property in 1962. It was purchased two years later by the Township of Etobicoke, which restored the Inn and opened it as a museum in 1975. Montgomery's Inn is the oldest building in Islington, and the third oldest in all of Etobicoke.