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.
The saltbox house at 566 Boston Post Road in Madison was long thought to have been built by John Dudley in 1675, making it the oldest house in town. The nomination for the Madison Green Historic District instead attributes it to Gilbert Dudley with a date of c. 1740. A plaque by the Madison Historical Society gives a date of c. 1720. On April 11, 1776, while on his way from Cambridge to New York, George Washington stopped to dine at the house, which was then a tavern run by Captain Gilbert Dudley.
The first meetinghouse in Madison was erected in 1705, on the southeast section of the town green. It had neither a bell nor a steeple and galleries were only added in 1715. A new meetinghouse was dedicated in May 1743, to which a steeple was added in 1799. The present First Congregational Church was built in the Federal style on the north part of the green in 1837-1838. As described in A Modern History of New Haven and Eastern New Haven County, Volume 1 (1918), by Everett G. Hill:
When the people built for the third time in 1838, they had the common struggle to break away from the green. There was a strong party that favored building on Deacon Hart’s lot north of the green, but so resolute was the minority that forty-seven members actually withdrew from the church in 1841, because of the change. The commanding site north of the green was chosen, and it and the building placed thereon have ever since been the pride of the people of Madison, the delight of all who visit the town. It is a building of notable architecture, acknowledged by all good judges to be one of the finest country churches of its type in New England. A handsome modern chapel was added to its equipment, on a plot just east of the green, in 1881.
The house at 542 Boston Post Road in Madison was built in 1789. It has a later three sided oriel window, which was added to the second story on the east side of the front facade. The house was the residence of Rev. John Elliott, who the third minister of Madison’s Congregational Church. As related by Rev. James A. Gallup in the Historical Discourse Delivered on the One Hundred and Seventieth Anniversary of the Formation of the First Congregational Church, Madison, Conn., November 18, 1877 (1878):
Rev. John Elliott, D.D., the third pastor of this church, was born in Killingworth (now Clinton), August 24, 1768. He was the son of Deacon George Elliott, and grandson of the Rev. Jared Elliott, M.D., of Killingworth (now Clinton), and great-grandson of Rev. Joseph Elliott, of Guilford, who was the son of the Rev. John Elliott, of Roxbury, well known as the Apostle to the Indians. He fitted for college in his native town, under the instruction of the Rev. Mr. Mansfield, his pastor, and entered Yale College in 1782. He took a high rank as a scholar, and graduated with honor in 1786. He devoted several years to teaching and the study of theology. He preached his first sermon July 11th, 1790, in Rev. Mr. Todd’s pulpit in East Guilford. During the last year of Mr. Todd’s ministry he was much of the time unable to preach, and, at his request, Mr. Elliott was employed by the society to preach for him. After Mr. Todd’s death the pulpit was supplied for a time by the neighboring ministers.
In November of 1791, Rev. Elliott was settled as the church’s new minister. He served until his death, on December 17, 1824. Quoting again from Rev. Gallup:
He was but twenty-three years of age at the time of his ordination. He is described as remarkably sedate, dignified and solemn in manner, judicious and exemplary in conduct, precise in speech, and methodical in all his movements. He was tall, slender, and erect in form, and wore always the cocked hat, short breeches, long waistcoat and stockings, and buckled shoes of the gentlemen of the ancient time. As he is remembered by some who hear me this morning, in the latter part of his life his head was bald and his hair white. His measured step and grave bearing, both out of the pulpit and in it, made him seem to his people the very embodiment of reverence.
[. . . .] Dr. Elliott was married November 3, 1792, to Sarah Norton, daughter of Lot Norton, of Salisbury, Conn. They had no children. His wife survived him, and afterwards removed to Salisbury. She was subsequently married to Gen. Sterling.
She married General Elisha Sterling of Salisbury in 1830 and died in 1841.