At 366 Main Street South and Doolittle Hill Road in Woodbury is a house built c. 1823-1824 by brothers Benjamin and George Doolittle. The brothers divided the house equally between them, including the basement (the house is on a hill and there is an entrance to it on the left side of the house, not visible in the image above), where Benjamin and George each had a Dutch oven. During the War of 1812, Benjamin Doolittle (1798-1868) was a drummer boy with the New Haven Grays. He became a cabinetmaker, manufacturing chairs in Litchfield, and moved to Woodbury in 1822. He was an active member of King Solomon’s Lodge, No. 7, of Free and Accepted Masons and of St. Paul’s Episcopal Church. From 1854 he ran an express business between Woodbury and New Haven, as well as routes to other points, such as Waterbury. He died en route to New Haven in 1868. The house remained in the Doolittle family until George’s widow, Betsey Collier Moore Doolittle, died in the Blizzard of 1888.
The small brick structure at 6 Main Street South in Woodbury was built in 1888 on land sold to the town by Charles Hurd with the stipulation that the town would retain use of it or ownership would revert to his heirs. The building served as the Town Clerk’s office from 1888 until 1952. It was renovated in 1986 by the Old Woodbury Historical Society, which uses it as a library and archive of old town records.
The house at 5 Judson Avenue, adjacent to the First Congregational Church in Woodbury, was built in 1829 by Benjamin D. Beecher. This is probably Benjamin Dutton Beecher, an inventor who built a steam boat propeller similar to the screw-propeller that would later be invented by John Ericcson. His career is described by Frederick J. Kingsbury in an article entitled “An Ericcson Propeller on the Farmington Canal” (The Connecticut Magazine, Vol. VII. Nos 3-4, 1902):
Benjamin Dutton Beecher was born at Cheshire, Connecticut, November 2, 1791, and was educated at the Academy there, the late Admiral Foote having been his school-fellow and life long friend. He learned the trade of a carpenter, and at the age of twenty-two, during the war with England, he invented the first fanning-mill for cleaning grain known to the world. This invention he patented May 13, 1816. In 1828 he was living in Woodbury, Connecticut, where several of his children were born. In 1830 or 1831, he removed to New York City. While living in Woodbury he received a patent October 20. 1830, for a grain-threshing machine. In New York he bought a steam tug-boat, which he commanded himself, and did a successful business and made improvements on the boat and engine. In 1832, when the cholera broke out in New York, he left with his family by packet for New Haven, and by canal to Cheshire. His son says that so great were the fear and the haste of their flight that they abandoned everything but the clothes that they wore, and that at some point they were quarantined for a considerable period in a barn. He then took up his abode in Cheshire, On the Mountain Brook road, near where the boat was built, and erected a shop with a water-power engine attached. When his dam broke away, being in a hurry to complete his boat, he invented and built a horse-power engine, which he patented in December, 1833. In one of his trips on the canal, Admiral Foote—then lieutenant—accompanied him.
In 1819 the Reverend Grove L. Brownell (1790-1855), the first minister of the North Congregational Church in Woodbury, acquired land where he soon (by 1824) erected a house. After Rev. Brownell left Woodbury in 1840, the house was deeded to three trustees, who then passed it on in 1845 to the church’s next minister, Rev. John Churchill (1811-1880). Between 1850 and 1853, Rev. Churchill moved the house to its current location at 94 Main Street South and built a larger house for himself on the original site. He sold the old house in 1855. The original rear of the house was replaced by a new addition around 1894.
The house at 6 Green Circle in Woodbury was built around 1823 for William Camp Cogswell (1796-1874). A merchant, Cogswell was twice married, first in 1821 to Frances Pomeroy Whittlesey (1801-1837); second in 1838 to Catharine A. Sherman. Cogswell ran a shop south of the house under the name Cogswell and Sherman. As described by W. A. Strong in a letter printed in The Town and People: A Chronological Compilation of Contributed Writings from Present and Past Residents of the Town of Woodbury, Connecticut (1901):
The pleasant days when I attended school in the old brown school house come back with greater force when the changes since that time are considered. Then the country store kept by Mr. Cogswell was where the people from far and near brought their butter and eggs to exchange for sugar, molasses, dry goods and Yankee notions. “Doc” was the presiding genius behind the counter, and we small boys looked with wonder and envy on the treasures he controlled. His fiddle was our delight and nothing could excel the music from his magical bow.
Woodbury‘s North Congregational Church was built by the Strict Congregational Society, organized in 1816 by members who had left the First Congregational Church of Woodbury. Work on building the church had already begun in 1814, two years before the society was officially organized. It was completed around 1818 and was dedicated on January 7th of the following year. The sermon at the dedication was given by Rev. Lyman Beecher.
Jabez Bacon (1731-1806) was a wealthy merchant who is thought to have been Connecticut’s first millionaire. In 1758 he acquired property on Hollow Road in Woodbury where he erected a grand residence by 1762. The house has original paneling in five formal rooms that each have a distinct design. The property, unusual for Connecticut, has the original detached summer kitchen with an intact smoke room on the second floor. This structure was once referred to as the “slave quarters.” Although Bacon had at least one indentured servant, Matthew Lyon, he is not known to have owned African slaves. There is also an early barn on the property. Bacon built a store next door, which is now used as a private residence. In 1834, the Bacon family sold the property to the Curtiss Family, who owned it until 1927. The next owners of the house were the Marvin family. Harlan H. Griswold (1910-1989), a leading Connecticut preservationist, purchased the house in 1953.
As a man he was one to make an impression on every one that came near him. The energy of the man was amazing, and, this directing all his powers to the single business of accumulation, wealth flowed into his coffers on every side. He was for years the sole merchant of this town and all the neighboring towns; and so large at times was his stock in trade, that, it is credibly reported, merchants from New Haven sometimes visited Woodbury, and purchased from Jabez Bacon goods to retail afterwards in that city.
His way of doing business was often rash, apparently, and seemingly no safe rule for others. An aged merchant of New York told the writer of this many years ago, that he (Mr. Bacon) would sometimes visit his store, make him a bid for a whole tier of shelf goods from floor to ceiling, amounting in value to thousands of dollars, and have the whole boxed and shipped in an hour to the sloop at the foot of Peck Slip bound for Derby. His vast wealth also, together with his business skill, sometimes gave him the command of the New York market so that, to a degree moderns can hardly credit, he could, with a turn of his hand, ” put the screws” on an article, and make its price in the great metropolis rise and fall like a barometer. An anecdote, an unquestionable fact, illustrates this. He was a large dealer in pork, this being the “circulating medium,” it would seem, for this region, judging from the vast quantities of it that found their way to “the old red store in the hollow,” as it was called, thence down to “Darby Narrors” where it was shipped to New York. The old gentleman had once shipped an exceedingly fine lot of this article for the city, but when he arrived there he found his purchasers indisposed to his price, as two immense ship loads were that day expected from Maine. The old gentleman merely set his teeth firm, an ominous trick of his in a bargain, and left the store. He instantly took a horse, rode some six miles up the East River shore, to about what is now Blackwell’s Island, boarded the sloops as they came along, and purchased every pound of their cargoes, staking his whole fortune for it. This at that day put the whole New York market in his hands, and tradition says he cleared forty thousand dollars by this single operation.
He was kind-hearted, open and generous, though in a bargain close to a fault. His hospitality was unbounded. A long table was kept set forth in the west parlor of what is now the residence of Daniel Curtiss, Esq., the whole year round. This might have been policy, but it was also a part of a large heart, that took pleasure in giving in this form. As a citizen he was public-spirited and useful for his day. As a husband and father his affections were endearing and indulgent, and he was the centre of a large circle of relatives and friends. But it was as a business man where he deserves to be noted; where he deserves signal mention for posterity. He was the centre of a great commotion; the main-spring of a mighty watch, such as we in this day almost consider apocryphal; and with him has passed away a business era, such as shall not soon be seen in this valley again.