The town of Elkhart was founded in 1855 by John Shockey, one of many who grew up along the Alton and Sangamon Railroad. In 1870 the Gillettes built their home on Elkhart Hill, but just a year later it was destroyed by fire. Two years later the house was rebuilt and on this land the Gillettes raised eight children. In the late 1800s, the town of Elkhart became one of the largest shipping ports on the Chicago and Alton Railroad, largely due to the success of Gillette's cattle operation. The Gillettes became prominent figures in central Illinois and made frequent trips to Europe.
Richard J. Oglesby, a three-time governor of Illinois and a close friend of Abraham Lincoln, married Gillett's eldest daughter, Emma, and built their house across from the Gillett house. Known as Oglehurst, the 46-room mansion had a pipe organ in the Great Hall, a fourth-floor schoolroom where the children were educated, and a music room. Years later, the manor house in Oglesby burned down.
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