Housed at the William L. Clements Library at the University of Michigan are the diaries of Jonathan Samuel Wilcox (1791-1875), a Madison storekeeper. Covering nearly thirty years (1844-1875), the diaries document Wilcox’s business and religious activities (he describes his church attendance and evaluates the sermons he heard there, sometimes after attending three sermons at three different churches on the same day), as well as his political involvement. A staunch Democrat, Wilcox was hostile to abolitionists and opposed the Civil War. Several of his children and other relatives lived in Augusta, Georgia (collections of family letters are held by libraries at Yale and the University of Georgia. Wilcox’s own house, built in the Federal-style in 1830, is located at 558 Boston Post Road across from the Green in Madison.
The book Madison: Three Hundred Years By the Sea (1976), p. 39, dates the Abraham Cruttenden (or Crittenden) House to 1639. Abraham Cruttenden was one of the original settlers of what would become Madison and he arrived in New Haven with other settlers of Guilford in 1639. A more recent dating of the house, which is a Colonial cape at 123 Boston Post Road in Madison, is 1735. In 1967, Yale architect Albert Riese erected a mid-century modern box at the rear of the house as a wing for his elderly mother. Riese’s daughter and her husband extensively renovated the house in 2012.
The Shelley House, at 248 Boston Post Road in Madison, dates to the late seventeenth/early eighteenth Century, with specific dates variously given that include 1709/1710 and 1730. This exceptionally well-preserved structure is a rare surviving example of a house that was clearly built in several stages, following a pattern believed to have been common at the time: starting with a one-room, two-story dwelling with a stone wall at one end (the east half), a second section added later (the west half) and finally a lean-to at the rear. Traditionally known as the William Shelley House and also known as the Stone-Shelley House, it underwent a controversial restoration c. 2008.
The large Italianate house with a cupola at 17-19 Wall Street in Madison was built in 1854. It was the home of Alva Orrin Wilcox (1799-1887). His entry in the 1893 book The Descendants of William Wilcoxson, Vincent Meigs, and Richard Webb, complied by Reynold Webb Wilcox, reads as follows:
Alva Orrin Wilcox, of Madison, Ct, son of Return of Madison, Ct., kept a hotel and ran a stage line from New Haven to New London, carrying the mail for thirty years, m. Sept. 27, 1826, Rachel, dau. of Billy Dowd, d. Aug. 21, 1889.