Gillespie is a city in Macoupin County, Illinois, United States, and part of the Metro East region of the St. Louis metropolitan area. The populati…Gillespie is a city in Macoupin County, Illinois, United States, and part of the Metro East region of the St. Louis metropolitan area. The population was 3,168 at the 2020 census. The first group of settlers arrived to the area of Gillespie in the late 1820s from Kentucky, Ohio, and Indiana. The township thrived in the 1830s, increasing in population and businesses. In 1835 the first schoolhouse was built. Gillespie was incorporated as a town in the spring of 1853. By 1904, the population rose to 3,100 and there were a number of businesses, churches, and schools. On January 29, 1905, a fire swept through the business district and destroyed most businesses and some homes.
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