The following data is extracted from A History of the Pioneer Families of Missouri - Montgomery County.
Samuel Crutcher and his wife, Elizabeth Lee, were natives of Patrick Co., Va. Their children were Elizabeth, Cornelia, Frank, Charles, and Samuel. The latter married Nancy James, of Virginia, and settled in Lincoln Co., Mo., in 1810, from whence he removed to Montgomery County in 1830. Their children were William, John, Sophia, Lucella, and Samuel, Jr. John was married first to Clemency White, and after her death to Mary J. Williams. Sophia married Sandy Jones, who settled in Montgomery County in 1831. Samuel, Jr., was married three times; first to Eliza Holladay; second to a widow named Holloway, and third to the widow Randolph, whose maiden name was Jane Winter. Lucella married John Darby, who settled in Randolph Co., Mo. Samuel and John Crutcher settled near Middletown, and the first goods sold in the northern part of Montgomery County were sold in one end of Samuel's house, in 1836, by Matthew Willburger and Samuel King. The latter sold out to Samuel Crutcher, and Willburger & Crutcher moved their stock of goods to the present site of Middletown, into a little log cabin, which was burnt soon after, and they were both ruined. Wiliburger surveyed and laid out Middletown in 1836, and John Dugan built the first house there. Stewart Slavens owned a part of the land on which the town was built.
Source: A History of the Pioneer Families of Missouri - Montgomery County