Commodore Thomas Macdonough was a Naval hero of the War of 1812 who defeated the British at the Battle of Lake Champlain in 1814. Earlier in the war he had overseen the construction of gunboats in Middletown and after the war made his home in the city. At 66 Spring Street in Middletown is the Commodore Macdonough Elementary School, which was built in 1924 and dedicated in 1925.
The Capitol Theater, at 350 (354) Main Street in Middletown, was opened in 1926 by two Italian-immigrant brothers, Alessandro and Salvatore Sareceno. The theater originally presented vaudeville and silent films, later becoming a movie theater. By the early 1930s, the theatre was being run by Salvatore Adorno, also an Italian immigrant, who had built the Grand Theater (later called the Palace Theater), located next door on Main Street, in 1915 and was leasing both the nearby Capitol and Middlesex theaters. The Capitol closed in 1975 and the lobby was converted to become a liquor store. The Palace Theater was demolished in 1980 to be replaced by the Middletown Transit Authority bus station. The 1892 Middlesex Theater was demolished in 1984, but the lobby was saved and is now home to the Tuscany Grill restaurant. Over the years the Capitol Theater became dilapidated. Its interior ornamentation had been removed and holes in the roof left the interior exposed to the elements. Trees were also growing on the roof! The building was declared unsafe by the city in 2009 and was finally demolished late in 2011. Today only the former lobby facing Main Street remains.
At 73 Main Street in Middletown is a house (pdf) that originally stood on William Street. It was built in 1747 for William Southmayd, who died before it was completed. His widow, Mehitable, was the house’s first occupant. It remained a residence until 1975 and was then slated for demolition. It was saved in 1977, when it was moved to its current address and converted to serve as offices.
At 291 Main Street in Middletown is a former U.S. Post Office, a limestone Renaissance Revival structure built in 1916. Planning for a new post office had commenced in 1911, but there was controversy over where to built it. Its location, at the southwest corner of Court and Main Streets, had been owned by the Federal Government since 1841. The Post Office ceased operations in 1977 and is now used by Liberty Bank.
The First Baptist Church, at 93 Main Street in Middletown, is a brick edifice built in 1842. The First Baptist Church in Middletown was first organized in 1795, 47 years before it moved into its current building.
The Charles C. Hubbard House, at 148 Broad Street in Middletown is an Italianate-style house built around 1861. It was the home of Charles C. Hubbard, who owned a hardware store on Main Street that sold products manufactured by Hubbard on Warwick Street. In 1873, Thomas W. Coit bought the house. He was a professor of ecclesiastical history at the Berkeley Divinity School. The school was established in Middletown in 1854 and moved to New Haven in 1928.