The oldest section of the building at 22 Knowles Road at Knowles Landing in Middle Haddam is possibly a house built on the site c. 1732-1735 by Jonathan Yeoman. For ten years (1735-1745), Yeoman ran a ferry across the Connecticut River. In 1747 the ferry licence was granted to Capt. Cornelius Knowles, for whom Knowles Landing is named. Jeremiah Taylor bought the Yeoman property in 1804, remodeling and expanding it in 1805 to serve as a tavern with a second-floor ballroom spanning the length of the building. The original one-and-a-half story, gambrel-roofed house became a two-and-a-half gable roofed structure. Taylor owned the building until 1826. The Italianate side veranda is a later addition. Jeremiah Taylor’s son, James Brainerd Taylor, was a minister during the Second Great Awakening whose life was a frequently used example of evangelical Protestant spirituality.
Located at the west end of the Willington Green is the Daniel Glazier Tavern. Built around 1815, the first recorded tavern keeper was Daniel’s son Isaac Glazier. The last tavern-keeper was Fielder Heath, who bought the property in 1839. The second-floor ballroom was used for town meetings in cold weather until 1840. The Tavern is thought to have been a station on the Underground Railroad. Charles T. Preston, a lawyer and Civil War veteran, bought the former tavern in 1881. His life is described in The Judicial and Civil History of Connecticut (1895):
Born in Willington, Conn., August 7, 1834. He was educated at the Connecticut Literary Institute at Suffield. He studied law with Hon. Richard Hubbard at Hartford, and was graduated at the Albany Law School. Admitted to the bar in Hartford county in March, 1858. He settled in practice in Hartford, serving during a portion of the war in the Twelfth Regiment of Conn. Volunteers. In 1867 he removed to Willington, where he is chiefly engaged in literary pursuits.
January 15, 1869, he married Mary E. Marsh, of New York city; she died May 2, 1871, and October 8, 1874, he married Carrie A. Preston.
At the northwest corner of the Boston Turnpike at 21 Bread & Milk Street in Coventry is a house built circa 1735 by John Wilson (1702-1773). After his death in 1773, the house passed to his son William (1729-1819), who married Sarah Rust, and his grandson Jacob (1749-1826), who married Hannah Dimmock in 1771. Jacob Wilson operated a tavern at the house from 1773 until 1817, when he sold the property to Joshua Frink.
Another early tavern in Coventry was the Pomeroy Tavern, at 1804 Boston Turnpike. It was built in 1801 by Eleazer Pomeroy II (1776-1867) to take advantage of the opening of the Boston Turnpike in 1804. By 1810 the Tavern was also a stage house where stagecoaches would stop (stages had previously stopped at the Hunt House to the west). Pomeroy placed some advertisements in the Hartford Courant seeking to sell the property in 1810-1811. One of these (appearing March 27, April 17 and May 29, 1811) reads:
That valuable and well-known stand, now occupied as a tavern and stage-house, situated in Coventry, north society, thirty rods west of the meeting-house, and sixteen miles from Hartford, on the great middle turnpike and stage-road from Hartford to Boston, and near the intersection of the Providence turnpike-road through Windham, with a large convenient two-story house and large stables almost new, and other out-buildings; and from 30 to 40 acres of choice land under high cultivation, well proportioned for mowing, pasturing, &c; with a well and aqueduct conveying water into the kitchen and barn. Said stand will be sold, a bargain, and possession given when wished.
Samuel Tracy Loomis (1819-1896), a farmer, acquired the property in 1868 and ran a hotel there until he moved to Andover in 1891. He also served as postmaster and the local post office continued to be at the building until 1905. Early stenciling from c. 1815 was found under later wallpaper in the hall on the building’s second floor.
The precise date for the construction of Brigham’s Tavern, at 12 Boston Turnpike in Coventry, is uncertain, but what is certain is that George Washington stopped here for breakfast on November 9, 1789. The full entry from Washington’s Diary for that day reads as follows:
Set out about 7 o’clock, and for the first 24 miles had hilly, rocky, and disagreeable roads; the remaining 10 was level and good, but in places sandy. Arrived at Hartford a little before four. We passed through Mansfield, (which is a very hilly country, and the township in which they make the greatest qty. of silk of any in the State,) and breakfasted at one Brigham’s, in Coventry. Stopped at Woodbridge’s in Et. Hartford [now in Manchester], where the level land is entered upon, and from whence, through East Hartford, the country is pleasant, and the land in places very good; in others sandy and weak. I find by conversing with the farmers along this road, that a medium crop of wheat to the acre is about 15 bushels—of corn, 20—of oats, the same —and in their strong and fresh lands they get as much wheat as they can rye to the acre—but in warm or sandy land the latter yields most. They go more, however, upon grazing than either; and consequently beef, butter and cheese, with pork, are the articles which they carry to market.
The tavern served travelers from 1778 into the nineteenth century. Uriah Brigham, son of Elnathan Brigham, had acquired the property in 1753 from Mathias Marsh. He occupied what is now the rear section of the building, which may date to c. 1717. His son Gershom Brigham was the first tavern-keeper, constructing the tavern sometime before it was first licenced in 1778. The west section was also built around that time or a little later. The sections of the building have been much altered over the years.
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 house at 1 Old Tavern Lane in North Haven was built in 1738 as a tavern by William Walter. It was first known as the Half-Mile House (it is located on a half-mile strip of land that was once part of East Haven but later given to North Haven). After the Revolution it was renamed the Rising Sun Tavern. After Walter, the Tavern was run by Gideon Todd (1737-1817) for many years. Todd also maintained the road and charged travelers at a tollgate. Gideon Todd served as a sergeant during the Revolutionary War and was made a state militia captain in 1787. According to tradition guns were hidden from the British during the War in a secret room above the tavern’s kitchen. The interesting story of Todd’s marriage is described in the The Todd Family in America (1920):
Prudence Tuttle was from Wallingford, Conn., her father being an officer there under the King. Gideon Todd was born in North Haven, Conn. Their marriage created a sensation in Colonial society. The Tuttle’s were a wealthy and aristocratic family and when young "Gid" Todd asked their daughters hand in marriage, he was haughtily refused. He was their equal by birth and lineage, but had his fortune yet to make, and they had other views for their daughter. One winter day, there was consternation and dismay in the Tuttle mansion; Prudence was missing and investigation revealed the fact that she had eloped, mounted on a pillon, behind her lover, they had ridden to North Haven and were married. Her parents disowned her and her name was never to be mentioned. As time passed, reports reached them that Gideon Todd was getting on in a remarkable way; accumulating property and esteemed by every one, and they thought it time to forgive the disobedient daughter; so, they loaded a cart with bedding, furniture, and other valuables, and started the hired man with it for her home, they going on horseback. Arriving there first, they found their son-in-law at home, and were courteously received. After a time, the cart drove up to the door and they then announced that they had brought some presents, when Capt. Todd said with dignity, “Time was when the furniture and bedding would have been acceptable, for when we were first married, we slept on the floor on a straw bed; but now I can supply my wife with every comfort, and your presents cannot come into the house; but you will always be welcomed.” And tradition has it, they returned home, as chagrined and mortified, as their neighbors were amused.