Most of the land that is now part of Upland was purchased by John Oswalt in the 1830s. He was a speculator, and believed that a canal connecting Indianapolis and Fort Wayne might pass through the area. The town was formed in the late 1860s by Jacob Bugher, who planned for it to be a depot point on the Indiana Central Railroad. The town's name comes from the fact it was believed to be the highest point on the rail line between Columbus and Chicago. By 1880, the town had a population of around 150 and included a school, two churches, several stores, a blacksmith shop, and a sawmill.