In 1849, Sylvester Bailey purchased the land at 103 Main Street in Middlefield and a year later had built a house. Bailey, a gunsmith, established a nearby pistol factory with his partners, Henry Aston, Ira N. Johnson, John North, Nelson Aston, and Peter Ashton. Bailey died in 1864 and the house passed to his three sons, who sold it out of the family in 1866. Three Polish immigrant families then successively owned the house.
The house at 19 High Street in Middlefield is thought to have been built c. 1750 by Asaph Chilson adjacent to his parents’ house on land they then owned. Asaph acquired ownership of the property, including both houses, in 1756 (his parents had moved to another house the previous year). He sold the property in 1759 to John Lyman and Abraham Camp, whose half-shares were soon acquired by Samuel Russell. In 1770, Russell sold the property (now having only one dwelling house) to Richard Miller. It remained in Miller’s family until it was acquired by Oliver Bailey in 1813. Bailey was married to Anna Wetmore, whose mother had been Richard Miller’s first wife. The surrounding neighborhood would become known as Baileyville after Oliver and Anner’s grandson, Alfred M. Bailey, who contributed to the area’s industrial development, building a dam at Lake Beseck c. 1850.
Located at 112 Main Street in the Rockfall neighborhood of Middlefield is a house built c. 1820 by Joseph Hale. He had received the land from his uncle in 1819, after his marriage to Julia Stow (died 1843). As executor, Hale settled the estate of his father-in-law, Joshua Stow, and then sold the house to Freeman Johnson in 1849. Hale moved to Ohio, where he died in 1855. Johnson sold the house to his son, Ira N. Johnson, who manufactured pistols. As related in the History of Middlefield and Long Hill (1883), by Thomas Atkins,
[the] Pistol factory was erected by a company of young men, namely, Henry Aston, Ira N. Johnson, Sylvester Bailey, John North, Nelson Aston, and Peter Ashton. They took a large contract of the government of the United States for making pistols; an additional contract was granted them. When the work was finished the property was put up at auction by the company, and Ira N. Johnson was the highest bidder, and the property came to him in 1852. Since then, the manufacture of pistols and other things has been carried on by Johnson and others up to the time the factory was burned, which was on the night of the 21st of Sept., 1879.
In the nineteenth century, as the Bayliville section of Middlefield developed into an industrial area, many houses were erected for local workers. A good example of one of these is the house at 53 High Street. It was built in 1866 by Martin Moon, who possibly worked at the Metropolitan Washing Machine Company. Moon purchased the land using the severance pay he received after his service in the Union army during the Civil War. The house was later owned by the Lyman Gun Sight Corporation.
The original St. Colman’s Catholic Church in Middlefield stood at the corner of Main and Stow Streets. The cornerstone was laid in 1886 and the church opened its doors on August 7, 1887. Construction was completed in 1889 and fourteen stained glass windows were installed the following year. It was a mission church under St. John Parish in Middletown until 1903, when it became a mission of the newly formed St. Francis Parish in Middletown. The last service in the old church was held on September 16, 1962, the same day that the new Church of St. Colman, located at 170 Hubbard Street, was dedicated. The church was granted full parish status in 1964.
The house at 274 Jackson Hill Road in Middlefield was built c. 1835 by William Hale. In 1838 he sold the house to Ichabod Miller. The house and extensive farmland remained in the Miller Family until 1886.
By the 1840s, the village of Rockfall in Middlefield was an active industrial area with a number of mills. Between 1845 and 1848, William F. Boardman built two boarding houses for workers on Main Street in Rockfall. The one pictured above is the west boarding house at 127 Main Street; next door is the east boarding house. Otis Smith, who owned the nearby Smith pistol factory, bought the west boarding house in 1873. In the twentieth century, many Polish immigrants settled in the area, including the Drega family. Juzef W. and Weronica Drega acquired the house in 1923. Today it is a two-family house.