Historic Buildings of Connecticut

Exploring the Nutmeg State One Building at a Time

Haddam

Captain John Smith House (1720)

Happy Thanksgiving!!! Here’s a Colonial house in Haddam, at 95 Jacoby Road. It was built in the first third of the eighteenth century, possibly around 1720. Around that time Stephen Smith came to Haddam from West Haven. He distributed land to his four sons in 1753, this house going to Captain John Smith (1728-1808), a seafarer. His son, John Smith, Jr., was a blacksmith. According to tradition he forged the links of a chain across the Hudson River intended to interfere with British shipping during the Revolutionary War. He also shod a horse for George Washington. John Smith III was an apprentice blacksmith under his brother-in-law Elisha Stevens, who later founded the J & E Stevens Company in Cromwell. The house remained in the Smith family until 1899. In the mid- 20th century the property was home to Joseph and Mae Harrington from New York who grew strawberries and grapes that were sold at Rozniaks in Higganum. Joseph Harrington was the author of the Lieutenant Kerrigan mystery series. The house is unusual in Connecticut for having a large cellar fireplace. The property also has a barn dating to 1725-1730 and a creamery shed that was connected to the house in 1978 to become a library.

Orrin Freeman House (1841)

The large brick Italianate villa-style house at 37 Maple Avenue E in Higganum was built c. 1841-1843 by Orrin Freeman, a wealthy bachelor. As a prominent local businessman, Orrin Freeman (1807-1880) was part-owner of a brickyard started by his father. He also ran the largest lumberyard and sawmill company in Middlesex County with his brother. They supplied lumber for the shipbuilding operations at Higganum Landing until 1862. Freeman also served as Judge of Probate. The house remained in the Freeman family until 1904. Eugene Orlando Burr purchased the house in 1908. Between 1910 and 1942 he ran a dairy farm known as Higganum Dairy. The house has continued in the same family ever since. In 1976, to commemorate the Bicentennial, Burr’s son-in-law, Francis Wright “Bill Gardner, Jr., who acquired the property in 1957, painted a large “Spirit of ‘76” mural on the house‘s southwest elevation. The house is now a bed & breakfast called The Spirit of 76 House.

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George E. Bailey House (1825)

The house at 1344 Saybrook Road in Haddam was built around 1825 by George E. Bailey. It is a late example of a gambrel-roofed Cape house more common to the later eighteenth century. In 1828 he sold the house to Jonathan Dickinson (1792-1861), a shoemaker.

Old Baptist Church, Haddam (1833)

The Shailer family of Haddam comprised a large portion of the membership of the Baptist Church that formed in 1792 and built a church on the south side of what was then called the Middlesex Turnpike in 1822. A new and larger church was built across the street in 1833, at what is now 1338 Saybrook Road in Haddam. The church closed its doors in 1907 and has since been used for other purposes, including a pottery studio and residence.

Ray-Ely House (1775)

The house at 1283 Saybrook Road in Haddam was built about 1775 by Benjamin Ray on land he had inherited, with his brother Peter, from their father James Ray (1689-1786) the year before. The brothers sold the property to John Ely in 1804. His son William sold the house in 1839 to the Odber family (William’s daughter Harriet had married John Odber).

Deacon John Shailer House (1840)

The house at 1212 Saybrook Road in Haddam was built around 1840 by John Shailer (1791-1887) on land he had inherited from his father, Lt. Thomas Shailer (1742-1813). A deacon in the Baptist Church, John Shailer was a farmer and school teacher. In 1856 Shailer and his wife Elizabeth Ventres Shailer, with their married daughter Amelia and her husband John Clark, moved to Somonauk, Illinois. The house was sold to Ezekiel Shailer (1810-1867), a tobacco farmer who was also a merchant in New York City. After his death the house was next home to Sorilla, widow of Bazaleel Shailer, until 1903.

Brainerd Hall (1795)

The house at 895 Saybrook Road in Haddam was built by the brothers Nehemiah and John Brainerd to serve as a social hall called Brainerd Hall. The brothers owned a granite quarry that they opened in 1792. Brainerd Hall was constructed soon after the brothers’ uncle Hezekiah Brainerd and his wife Elizabeth acquired the land from Elizabeth’s father, John Wells, in 1794. After John Brainerd’s death in 1841, the hall housed students at the nearby Brainerd Academy, a school established by the Brainerd brothers.. After 1857, Erastus G. Dickinson operated the Golden Bull Tavern in the building. It remained in the Dickinson family until 1964.