The large brick Italianate villa-style house at 37 Maple Avenue E in Higganum was built in 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.
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.
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.
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).
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.
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.
The grand Italianate house, now used for commercial purposes, at 263 Saybrook Road in Higganum in Haddam was built in 1875 as the home of Thomas J. Clark (1831-1910). He was a founder of the Higganum Manufacturing Company, later called Cutaway Harrow, which produced farm equipment. As described in The Conservative Advocate: a Book of Biographies of Connecticut’s Successful Men (1900)
Thomas J. Clark, Vice President of the Cutaway Harrow Company, is as well known as any man in Middlesex County. He was born in Haddam, September 21, 1831, and with the exception of two years spent in Georgia and Florida, has always resided there. He attended Rev. James Noyes’ private seminary in Haddam and then engaged in the business of stone cutting. Later he became a house builder. Since 1865 he has manufactured farm implements. He has been a life long Republican and is a member of the Congregational Society, He is president of the Higganum Savings Bank, a member of the Granite Lodge Masons and has represented his town acceptably in the Legislature. Mr. Clark is most highly esteemed and is a splendid type of the sturdy New Englander.
When he was but 15 years of age, he commenced working in the quarries and doing odd jobs of mason work. The strong spirit of self-reliance and independence were manifested at this early age, and thee years later he started for Apalachicola, landing there in the fall of the year an entire stranger. He didn’t sit down, Micawber like, “waiting for something to turn up,” but soon after engaged as an assistant in the engineer’s department of a cotton pressing establishment. He soon learned to run an engine and earned good wages as an engineer. For two or three years he spent his winters at Apalachicola, and his summers at the north working at his trade as a stone mason. For several years after this he was engaged in the construction of important works at different places, among which was the Asylum Street Depot in Hartford, erected in 1848. He subsequently entered into partnership with his brother, George M., taking large contracts for the erection of bridges, mill works, factories, etc., the stone and mason work being entirely under his supervision. He was engaged with his brother in the erection of the Russell Manufacturing Company’s building at Higganum, and soon after this started with his brother the extensive manufacturing business now carried on by the Higganum Manufacturing Company.
Mr. Clark is modest and retiring in his habits, but possesses those sterling qualities which go to make up the solid men of our country. He has never sought political honors, but attended quietly to his business affairs, and has aided materially in the development of one of the most prominent branches of industry in this country. In this he is now, and has been from the commencement of the business, and important factor. He is vice-president and has the general management of the mechanical department of the Higganum Manufacturing Company.
On the 7th of December 1854 he married Elizabeth Quick, of Masthope, Pa., by whom he has had four children: Arthur, born August 2d 1858; Effie Elizabeth, born December 21st 1860; Alvan Thomas, born October 14th 1862; and Ada Selden, born February 24th 1871.
The death of the his first wife occurred on the 13th of July 1873, and on the 4th of November 1874 he married Sophia M. Warner, of Montrose, Pa. One child, Nina Gertrude, is the issue of this marriage.
Until quite recently Mr. Clark has taken no active part in public affairs, but during the fall of 1884 the people of his native town insisted on his accepting the position of selectman, which his long experience and thorough knowledge of the duties incident thereto fully qualify him to fill.