16 Barry Road, Oxford (1740)

The house at 16 Barry Road in the Quaker Farms section of Oxford was once thought to have been built as early as 1680, but a date of 1740 is now considered more likely. In the early nineteenth century the house was owned by the Tomlinson family. It was used in the mid-nineteenth century by Preston Hinman for his shoemaking business. Greatly deteriorated by the early twentieth century, Ralph B. Pomeroy purchased it in 1947, removed a later dormer window and undertook the house’s restoration to a colonial appearance.

Ebenezer Dayton House (1730)

The house at 388 Amity Road in Bethany was built c. 1730. Its earliest known owner, c. 1780, is Ebenezer Dayton, a privateer of the Revolutionary War. A dramatic robbery took place in this house in 1780. The robbery was planned at the Turel Whittemore Tavern in Seymour. The incident is described by John Warner Barber in Connecticut Historical Collections (1836):

On the night following the 14th of March, 1780, the house of Capt. Ebenezer Dayton, then residing in this place, was broken into and robbed by seven men, who were tories, and headed by a British officer, from Long Island. Mr. Dayton’s house was situated nearly opposite where the first meeting house in Bethany was erected, about half a mile south of the present Congregational church, and about ten miles N. W. of New Haven.

The particulars of this robbery, were obtained from the Rev. Mr. Dayton, son of Capt. Dayton, mentioned above. Mr. Dayton, who belonged to Long Island, was on account of his attachment to the American cause, obliged to leave that island, and bring his effects with him to Bethany. A number of men, some of his neighbors, were obliged to leave the island for the same cause, and brought a considerable quantity of money with them, and for a while resided in Mr. Dayton’s house. With these facts, the robbers appear to have become acquainted. At the time of the robbery, Mr. Dayton was absent on business at Boston, and the men who had been staying in the house, had left the day before, so that there was no one in the house but his wife, Mrs. Phebe Dayton, three small children and two servant colored children. About midnight while they were all asleep, the window in the bedroom where Mrs. Dayton was sleeping, was burst in at once, seven armed men rushed in, passed through the room and immediately rushed into the chambers, expecting (it is supposed,) to find the men who had left the day before. While they were up stairs, Mrs. Dayton went to the front part of the house, raised the window and endeavored to alarm the neighbors. Mr. Hawley, the minister of the parish, and Dr. Hooker, the physician of the place, both lived within 20 rods distance; both had lights in their houses at the time, and both heard the alarm, but did not know from whence it proceeded. The robbers hearing Mrs. Dayton, came down, and tearing a sheet into strips tied her hands behind her, made her sit in a chair and placed her infant (about six months old,) in her lap, while one of the robbers placing the muzzle of his gun near her head, kept her in this position for about two hours, while the house was thoroughly ransacked from top to bottom. They found about 450 pounds in gold and silver, which belonged to Mr. Dayton, besides other valuable articles; what they could not conveniently carry off they wantonly destroyed, breaking in pieces all the crockery, furniture, &tc. The whole amount of property carried off and destroyed, including bonds, notes, &c. amounted to five thousand pounds.

The robbers left the house about 2 o’clock and went to a place in Middlebury, called Gunn town, where they were secreted in a cellar by a family who were friendly to the British cause. While they were on their way to Gunn town, they met a young man by the name of Chauncey Judd of Waterbury, on a bridge, who had been to see the young lady he afterwards married. Fearing he might discover them, they took him along with them. In the cellar kitchen where they were all secreted, there was a well. Into this well they talked of putting Mr. Judd; but the old lady of the house begged they would not think of it, as it would spoil the water. They stayed in this house a number of days: afterwards they went to Oxford, where they were secreted for several days longer in a barn; from thence they went to Stratford, took a whale boat and crossed over to Long Island. The people at Derby, having received information of their passing through that place two whale boats and crews, commanded by Capt. William Clarke and Capt. James Harvey, pursued them to the Island, and were fortunate enough to catch them all but one, just within the British lines. They were brought back, tried condemned and sent to Newgate; they however, broke prison and finally fled to Nova Scotia.

In the 1830s the house was owned by Colonel Elihu Sanford. In 1929 the house was moved 300 feet north of its original location to its current address.

Deacon Joseph Ives House (1724)

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.

Howard House – Methodist Parsonage (1790)

The house at 89 Tolland Green in Tolland was built c. 1790 by a member of the Howard family. Bishop Francis Asbury, who played a major part in the spread of Methodism in the United States, held a conference of Methodist ministers in the house in August 1793. As related in the Life and Labors of Francis Asbury, Bishop of the Methodist Episcopal Church in America (1896), by George G. Smith:

Methodism had come to New England to stay, and the Conference was to meet at Tolland. With a blister behind his ear for a sore throat and a poultice on his foot for rheumatism, he consented to rest a little while, but only for two days. He was again attacked by the rheumatism, and was not able to walk from his horse to the house, and had to be lifted down from the saddle and up again.

As Bishop Asbury noted in his own Journal:

Our conference sat at Tolland. Lame as I was, I went through the business; and notwithstanding I was tired out with labour, heat, and pain, and company, I must also preach; so I submitted; and endeavoured to apply 2 Tim. ii, 24-26.

As explained in the Souvenir History of the New England Southern Conference in Three Volumes (1897)

The preaching service was held in the partially finished chapel. Bishop Asbury was present and preached on II. Timothy ii: 24-26, “The servant of the Lord must not strive,” etc. The text was peculiarly apt for the people and the time, for Dr. Williams of the Congregational Church had recently bitterly attacked the Methodist Church usages and doctrines. Dr. Williams afterwards acknowledged his mistake, and invited Methodists to hold prayer meetings at his home.

In 1794 Bishop Asbury again stayed at the house, which later became a Methodist parsonage for a time.

Abraham Cruttenden House (1735)

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.