Deacon Joseph Ives (1674-1755) was one of the first settlers in what is now Cheshire. He built the house at 280 Fenn Road in Cheshire in 1724. As related in J. L. Rockey’s History of New Haven County, Connecticut, Vol. I (1892):
In the southeast portion of the town and near the residence of Mrs. Silas Ives, Joseph Ives settled in the year 1694; the same year of his marriage to Esther Benedict. He was one of the first, if not the first settler, in what is now Cheshire. He was chosen the first deacon of the Congregational church in 1724, and served the church in that capacity until the year 1739, at which time the second church edifice was erected. Deacon Ives was a very useful and devoted member of the infant parish. In this same house also his son Joseph and grandson Titus resided. The latter was a revolutionary soldier and was with Washington’s army at Harlem, N. Y., where he died in the year 1777. A letter written by his wife, and sent to him at Harlem, during his last sickness, and also the gun used by him in the colonial struggle for independence, are now extant and are preserved as precious memorials by the family of Mrs. Silas Ives, who are descendants, who reside within a few feet of the old Ives homestead, and who own and occupy the same property that has been in the possession of Deacon Joseph Ives and his descendants for about 200 years.
The Colonial Cape at 87 Main Street in Cheshire was built c. 1740 and was originally the home of Ebenezer Bunnell (1713-1786). A succession of families owned the house, including Ira Bronson of Wolcott, who operated a blacksmith shop on the property from 1834 to 1842. It is also known as the Belknap House.
The house at 62 Cook Hill Road in Cheshire was built c. 1740, with a wing added in the twentieth century. The house is called “The C.B. Bradley House” in Edwin R. Brown’s Old Historic Homes of Cheshire (1895). Brown writes:
This house was built by Moses Bradley, and is about 140 years old. Here, Oliver, a son, Columbus, a grandson, and Charles B., a great-grandson, resided. In this house, Stephen Rowe Bradley, a son of Moses, was born Oct. 20, 1754, and here he spent his youthful days. As a boy, he was full of mischief, and seemed naturally inclined to play tricks on others. On the turnpike, but a few rods across the lot, Moses Peck lived, in an old-fashioned, lean-tn house. One night, when the family was absent, young Bradley selected this place for one of his exploits.
Inducing other boys to join him, he took the owner’s cart, which was left in the yard, near the house, separated the parts, and, as the back roof reached to within a few feet of the ground, with the aid of ropes, he drew up to the top of the roof, first, the neap and axle, and then, in the same manner, the wheels, and then the body. These separate parts were all put together on the top of the roof, one wheel being stationed on the west roof, and the other on the east, the neap resting on the ridge boards. They then drew up in baskets a sufficient quantity of wood to fill the body of the cart. So that an ox-cart, literally filled with wood, was plainly visible on the top of this house the next morning.
The owner, Mr. Peck, upon his return home, missing his woodpile and seeing other evidence of mischief, made inquiries of his neighbors, who called his attention to the exhibition on the housetop. Mr. Peck at once exclaimed, “Those cussed boys! I’ll fix ’em! I know very well who done it.” Stephen was watching the proceedings from a window in his father’s house with evident delight. This element of mischief seemed to grow as the years increased, and his father came to the conclusion that he could do nothing with him at home, so he decided to send him to Yale College. He at once commenced his preparatory studies under the instruction of the Reverend John Foote. He entered Yale College in the year 1772. As a student at Yale, the elements of sport and mischief in his nature did not lie dormant, but were manifested on several occasions, of which we have record and which evince his natural shrewdness.
[. . .]
Stephen Rowe Bradley graduated at Yale, in the year 1775, with honors. He afterward settled in Vermont, and became one of the most popular men of that State. He was elected to the United States Senate in 1802, and continued a member for 16 years. He was prseident [sic] of this body in 1802, in 1803 in place of Aaron Burr, and in 1808 and 1809 in place of George Clinton. He died at Walpole, N. H., in 1830. aged 75 years.
A remarkable career! Youthful activity, finding expression in mischief, as a boy, became the source of energy and power in mature life.
The house at 1151 South Main Street in Cheshire was built c. 1790-1800. It was the home of Amasa Hitchcock (1739-1827), a veteran of the French & Indian War [not to be confused with another Amasa Hitchcock (1768-1835), Cheshire’s first post master, whose house on South Main Street is no longer standing]. The house remained in the Hitchcock family until 1975.
This house was built by [Col.] Benjamin Hall for his son, Charles Chauncey Hall, about the year 1750, and is one of the best examples of the old, lean-to houses, with stone chimney, now standing. Charles Chauncey Hall married Lydia Holt in 1751, and a large family were born and brought up here, among whom was Charles C, the grandfather of Charles H. and Frank N. Hall, also Benjamin Holt Hall, who also resided here during his life. Two daughters of the latter married Joseph Hitchcock, the father of Samuel. Another daughter married Capt Asa Peck, and another married George Peck, who lived here. Charles C. Hall, while a resident, held a negro boy as a slave. The boy ran away, and Mr. Hall advertised his escape, offering a reward of $2 for his capture. Charles Chauncey Hall died in 1776.
It is related of George Peck, a later resident, that in the days of the militia he was duly appointed corporal of the Cheshire company. Stepping up to the top-most step of the Congregational Church, he remarked: “I thank you for the honor conferred upon me by appointing me your corporal. I feel abundantly qualified for the position, but I shall not accept.” This speech was in keeping with Mr. Peck’s ready wit.
This property has been in the hands of Col. Benjamin Hall and his direct descendants for 170 years. If this old house had the power of speech, what a life history it would be able to disclose!
The house at 107 Cornwall Avenue in Cheshire was built in 1855. The house has been renovated a number of times over the years. The current doorway and front entry porch are thought to be the work of local architect Alice Washburn.
The brick house at 273 South Main Street in Cheshire was built c. 1850. It is transitional in style between the Greek Revival and the Italianate Villa. Two owners of the house in the mid-nineteenth century were E. Talmadge and U. P. Hokum.