Little Red Schoolhouse, Winchester (1815)

Located at the intersection of Platt Hill and Taylor Brook Roads in Winchester is a one-room schoolhouse built in 1815 to replace an earlier one on the same site that had burned down in the 1790s. The new building, Winchester’s District No. 8 schoolhouse, was heated by a fireplace until a box stove was installed in the 1830s. The schoolhouse was in use until it closed in 1908. It then remained abandoned for the next eight years. In 1916, William H. Hall, a historian for whom Hall High School in West Hartford is named, expressed his concern for the neglected building in an article Winsted Evening Citizen. This inspired Clifford Bristol to buy and repair the building. Bristol had been a student at the school about 1870 and his father, Charles A. Bristol, had been a teacher there. In June of 1916, Bristol held a reunion in the school of former teachers and students. In 1923 another meeting was held in the building which formed the Little Red Schoolhouse Association, dedicated to preserving the historic building. The organization’s membership had dwindled by the early 2000s, but in recent years there has been renewed interest and fundraising efforts to allow restoration of the building to its original condition. The restored schoolhouse reopened to the public in 2018. Other Connecticut buildings called “The Little Red Schoolhouse” can be found in North Branford (built 1805) and Wethersfield (built 1869).Bristol held a reunion in the school of former teachers and students. In 1923 another meeting was held in the building which formed the Little Red Schoolhouse Association, dedicated to preserving the historic building. The organization’s membership had dwindled by the early 2000s, but in recent years there has been renewed interest and fundraising efforts to allow restoration of the building to its original condition. The restored schoolhouse reopened to the public in 2018.

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Nathan Smith House (1735)

The house at 140 Burrows Hill Road in Hebron was built c. 1735–1744 by a Mr. Porter. It was purchased by the Smith family in 1794 and remained in that family until 2009. Nathan Smith, the second Smith to live in the home, remarried at age 65. In 1853, he added the Greek Revival north ell, where his father lived after retiring from farming. It is one of three additions that have been made to the house’s north side. There is also a kitchen addition at the rear of the house.

The Smith farm grew to hundreds of acres and included Prophet’s Rock, the town’s oldest historic landmark. The legend of Prophet’s Rock is related by Gov. John S. Peters in his “Historical Notes,” written in 1843 and quoted by F.C. Bissell in Hebron, Connecticut Bicentennial (1908). A group of men from Windsor had set out to explore and find places to settle in the area.

While the men were making preparations for their families in the summer of 1706 they brought their provisions with them and remained for weeks at their new home. Their wives being anxious for the welfare of their husbands and unwilling to be left too long alone, four or five started one shining morning for the promised land, twenty long miles through the wilderness, regulating their course by marked trees and crossing the streams on logs felled for that purpose. Night overtook them in the lower part of Gilead, they wandered from the line and brought up on the hill south of Nathan Smith’s house. Fearing the wolves would regale themselves upon their delicious bodies they concluded to roost upon the top of the high rock on the summit of said hill. Here they proclaimed their lamentations to the winds. This novel serenade attracted the attention of their husbands, who wandered towards the sound until they fortunately but unexpectedly found their wives on the rock, which they had chosen for their night’s repose. The gratification of the interview can be better imagined than expressed.

The location of this rock has been handed down to the present time and it is now known as “Prophet’s Rock.”

In 2003, when the Smith family had decided to develop part of their land off Burrows Hill Road, Prophet’s Rock and an easement to reach it from Burrows Hill Road were deeded to the town.

Jesup House (1810)

At the beginning of the nineteenth century, Ebenezer Jesup (1767-1851) was a resident of the Green’s Farms section of what is now the Town of Westport. Jesup was a grain dealer whose ships traded with Boston and other ports. Because his wharf and warehouses were along the Saugatuck River, he decided to build a home closer to his place of business. About 1807-1810, he erected a house that was considered to be the finest mansion in Fairfield County at the time. The community of Saugatuck would continue to develop, becoming the commercial center of Westport, which was incorporated as a town in 1835. In 1884, Ebenezer’s grandson, Morris K. Jesup (1830-1908), gave the house and eight acres of land to the Saugatuck Congregational Church, which was then located across the Post Road. He stipulated that the property was to be used as a parsonage and site of a future meeting house. In 1950, the Saugatuck Congregational Church’s meeting house, originally built in 1832, was moved onto the donated Jesup property. The Jesup (or Jessup) House, still used by the congregation today, is considered a great example of Federal style architecture. The house was photographed in the 1930s for the Historic American Buildings Survey. Photographs and measured drawings can also be found in The Architectural Forum, Vol. 33, No. 6 (December, 1920).

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Samuel Babcock House (1851)

Samuel Babcock (1788-1851) was a prominent Middletown manufacturer and politician. Originally from Old Saybrook, he was a silversmith there and around 1812 came to Middletown, where he had a shop near the Episcopal Church. In the 1850 census, he was listed as a spectacle maker (eyeglass manufacturer). He was active in various businesses, including banking, granite-quarrying and railroads. About 1851 he erected an Italianate house on Main Street, in front of Mortimer Cemetery. In 1927, the house was moved to 64 Liberty Street, across from the cemetery to make way for commercial development. At its new location, Salvatore Muscatello, the new owner, converted the second floor into a rental apartment and detached the original rear wing to become a separate house at 5 Frazier Avenue.

Mayo S. Purple House (1909)

The Colonial Revival-style house at 142 Main Street in East Hampton has a Queen Anne-style octagonal side tower. The house was built in 1909 or 1910 by Mayo Smith Purple (1860-1942), a prominent businessman in East Hampton. For 35 years he worked for the Bevin Bell Company, eventually becoming the company’s secretary. Around 1914 he assisted in the reorganization of the Gong Bell Manufacturing Company, subsequently serving as that company‘s president for about 28 years. His other positions included president of the Watrous Manufacturing Company, treasurer and manager of the East Hampton Bell Company, and in the mid-1920s treasurer of the Bevins and Wilcox Line Company. Purple also served in the state legislature for a term in 1885-1886 and returned almost a half-century later for four consecutive terms from 1932 to 1940. In 1883 he married Gettine Louise Arnold, who died in 1935.

Col. Daniel Brainerd House (1780)

Col. Daniel Brainerd (1752-1809), a farmer, built the house at 275 Saybrook Road in the Higganum section of Haddam about 1780. His sons inherited the house, but it was their sister, Zeruah Brainerd (1786-1877), who lived in it until her death. In the early twentieth century, the house was occupied by Owen Brainerd (1865-1919), an architect who worked with Carrere and Hastings of New York. He designed St. Peter’s Roman Catholic Church (now used as a private residence) on Saybrook Road.