Pictured above are two buildings on Main Street in Middletown that are joined together with a bracketed cornice. The one on the right, 420 Main Street, was built between 1867 and 1868 by Ephraim Sheldon, who had his furniture store in the building until 1892. The building was modernized c. 1895 with a Pompeian brick facade and brownstone window surrounds. Probably around that same time the cornice of the adjacent Fagan Building was extended across the Sheldon Building. Fagan’s Block, at 422 Main Street, was built in 1868 by Patrick Fagan. After his death in 1869, his sons continued their father’s real estate business with an office in the building. They added an addition on the north side that was demolished in the late 1930s to make way for the Woolworth Building.
The Middletown chapter of the Alpha Delta Phi literary society, based at Wesleyan University, was formed in 1856. The fraternity’s first chapter house was built in 1884. It was demolished twenty years later and replaced on the same lot (185 High Street) by the current building (completed in 1906) designed by Charles Alonzo Rich (who also designed two dozen buildings at Dartmouth College between 1893 and 1914). An addition was built onto the rear in 1925. Alpha Delta Phi has been coed since 1972 and is one of the coed chapters that withdrew from the fraternity to form the separate Alpha Delta Phi Society in 1992.
The building at 489-493 Main Street in Middletown was built in 1905 for the F.L Caulkins Auto Company. Known as the Caulkins Garage, it had an automobile showroom on the first floor with residences above. It was constructed when the company was expanding its automotive business from its quarters across the street, in the 1890 Caulkins & Post Building. The garage building continued to serve its original purpose throughout much of the twentieth century. The building is now home to Luce Restaurant (98 Washington St #1).
The Middletown National Bank, formerly the Middletown Bank, was chartered October 29th 1795. The organization was not completed, however, until May 1st 1801. The stockholders met at that time at Mrs. Sarah Goodwin’s Tavern and elected the following directors: Elijah Hubbard, Chauncey Whittlesey, Nehemiah Hubbard jr., Samuel Watkinson, Benjamin Williams, Ebenezer Sage, George Hallam, Joseph Hart, and Elias Shipman.
The first meeting of the directors was held May 13th 1801. Elijah Hubbard was chosen president, and Timothy Southmayd, cashier.
The bank constructed a building on Main Street in 1813, replacing it with a brownstone structure in 1855-1856, which was enlarged in 1893. This building was then replaced in 1917 by the bank’s third building on the site (267 Main Street). The Middletown National Bank was bought by the Connecticut Bank and Trust Co. in 1957. The building is now a branch of Bank of America. Read the rest of this entry »
The Southmayd Building, at 542-544 Main Street in Middletown, is an outstanding example of a nineteenth-century commercial block with a cast-iron facade. It was built by George M. Southmayd, who was in the undertaking business. His father John B. Southmayd had started the business at his home, which stood on the same site. In 1911 Ludwig Krenz bought the building (It is also known as the Southmayd-Krenz Building) and opened a bar and restaurant and it has been used for that purpose ever since under various owners. Read the rest of this entry »
O’Rourke’s is a world famous diner in Middletown. Located at 728 Main Street, the diner was built by the Mountain View Diner Company (it was manufactured in 1946 and has the serial no. 223). In 1930 “Pete the Greek” Asvestras moved his lunch wagon here and by the 1940s James Dunn was running Dunn’s Diner on the spot. John O’Rourke purchased Dunn’s Diner in 1941 and soon acquired the Mountain View dining car as his business expanded. The diner, which did not have fire insurance, suffered severe fire damage in 2006 after a hamburger steamer was left on overnight. A fundraising campaign with support from the local community and around the world led to successful renovations and the diner reopened in 2008.