At 712 Main Street in Middletown is the New Hope Bible Way Church. The building, which originally stood on the west side of Main Street between College and Court Streets, was built in 1799. It was then the fourth meetinghouse of Middletown’s First Church of Christ, a Congregational society first organized in 1668. The structure has been moved twice. The first time was in 1822, when it was shifted back 8 feet as it was thought to be too close to Main Street. In 1873, after the congregation moved to a new building (the current First Church of Christ on Court Street), the old meetinghouse had its steeple removed and the structure was relocated to its present location. The original rear of the church became the new front facade facing Main Street, to which storefronts were eventually added. For a time, the former church’s audience room was used for meetings of St. Mary’s Total Abstinence and Benevolent Society. Before becoming a church again, the building housed small businesses and apartments.
The present style of the front facade of the building at 191 to 195 Main Street in Middletown dates to c. 1891, when the original two-and-one-half story structure with a gable roof was raised to a full three stories. The north section of this commercial building was built in 1835 by Joshua Stow, a former county judge and Middletown post master (also a politician and ardent Jeffersonian Republican) who operated a store. In 1845 the building passed to William Trench, who rented it out to various commercial tenants. From 1882 to 1887 it was rented by the Middletown Police, who used it as the town’s first police station. The matching south section of the building was in place by 1856 (and may have been built at the same time as the north half (1835), with the brick fire wall down the center of the building being shared by the owners of the two separate halves).
The Greek Revival house at 61 Main Street in Middletown was built in 1837 for John Cookson, who was pastor of the First Baptist Church from 1828 to 1839. The house originally stood on the east side of South Main Street, opposite the church, which is no longer standing (the current Baptist church was built further north on Main Street in 1842). The house was purchased by the city’s Redevelopment Agency in 1972 and in 1977 it was moved to its current address as part of the South End Restoration project. It is now used as offices, as are two other historic houses that were relocated as part of the project: the William Southmayd House and the Caleb Fuller House.
The building at 484-494 Main Street in Middletown, built in 1889-1890 and considered one of the first “modern” stores in town, was once home to the Caulkins & Post Company. The business sold carpets, drapes and furniture and soon expanded to sell automobiles around 1903. This latter business was so successful that the company erected a building for its car dealership across the street in 1905. The company changed its name to F.L. Caulkins and Co. in 1906.
The building at 360 Main Street in Middletown was built circa 1873-1876 to replace an earlier structure, a hotel called that Kilbourn House, that had burned down. The new building served as a hotel, known as the Farmer’s and Mechanic’s Hotel and later the Hotel Chaffee. In 1905 the building was sold to the Pythian Building Corporation. From then on, the first floor has contained retail businesses (Woolworth’s was here in the 1920s and 1930s). The second floor was converted for office use and the third floor became the meeting space of the Knights of Pythias, a fraternal organization. The Pythian Building‘s current facade, with marble and large windows on the first two floors and a Palladian window on the third story, dates to 1938.
The building at 179 Main Street in Middletown was built in 1867 to house the office of the Middlesex Mutual Assurance Company (established in 1836) and commercial tenants. The third floor contained a meeting hall for fraternal organizations. A rear addition was built in 1891 to accommodate the Southern New England Telephone Company and behind the addition a theater was constructed in 1892. The third floor then was used for lounges for theater patrons. The Middlesex Mutual Assurance Co. moved to a new building on Court Street in 1927.
St. Francis of Assisi Parish was established in 1903 to serve the South Farms section of Middletown, as well as the towns of Durham and Middlefield. The parish’s first pastor, Rev. Patrick McGivney, was the brother of Fr. Michael McGivney, the founder of the Knights of Columbus. The parish’s new church (10 Elm Street in Middletown), built at a cost of $27,000, was dedicated on November 4, 1904.