The Main Street Historic District encompasses the historic commercial center of Middletown, Connecticut, United States. Middletown was one of the most important ports in America in the Colonial period, and Main Street "has been the center of community life since the earliest period of settlement". Today Main Street is home to a number of 19th century buildings, maintaining the bulk of its historic character. It was listed on the National Register of Historic Places in 1983.
According to the National Register of Historic Places (NRHP) nomination for the district, two properties in the district—the Church of the Holy Trinity and the Old Middletown Post Office are already on the NRHP in their own right. Three other individual properties were determined to be for NRHP status in their own right: the Arthur Magill, Jr. House/Chase School at 631 Main Street, the Main Street Firehouse at 533 Main Street, and the North End Meeting House at 710-712 Main Street. More generally, the entire block on the east side of Main Street from Washington to Ferry Streets, and numbers 560-614 from Ferry to Green were determined to be eligible.
Contributing properties according to the National Register of Historic Places (NRHP) nomination for the district (1983):
225 Main Street, Farmers & Mechanics Savings Bank, 1920237-45 Main Street, Nehemiah Hubbard House, before 1788, major Greek Revival style remodeling. (No longer extant 2012: 225 Main Street has an annex on this site.)267 Main Street, Connecticut Bank and Trust, 1920, Renaissance Revival (Prior to use by CBT, was Middletown National Bank)291 Main Street, Old Post Office, 1916, Renaissance Revival315 Main Street, Middletown Savings Bank, 1928, Academic Classicism319-323 Main Street, Old Banking House Block, 1796 - south section; 1815 - north section335 Main Street, Guy & Rice Building, 1930, Renaissance Revival339-351 Main Street, Commercial Building, 1892, originally erected as YMCA354 Main Street, The Capitol Theater, 1925, Neo-Classical Revival357-359 Main Street, Hubbard-Holland Building, 1873360 Main Street, Pythian Building, ca. 1874, remodeled 1938, Renaissance Revival detail363 Main Street, Central National Bank Building, 1915, Renaissance Revival detail, remodelled 1980366-386 Main Street, James H. Bunce Company, ca. 1920, early Modern Commercial381 Main Street, The Church of the Holy Trinity, 1871-1874, Gothic Revival, Henry Dudley architect388-392 Main Street, Wrubel Building, early 20th century, contemporary marble facing over Art Deco facade (now Main Street Market)393 Main Street, City Savings Bank, ca. 1915, Colonial Revival412-416 Main Street, R.W. Camp Company, 1920, Renaissance Revival418-420 Main Street, Sheldon Building, 1866, mid-19th century Commercial422-426 Main Street, Pagan's Block, 1868, Victorian Italianate437 Main Street, Commercial Building, early 20th century commercial428-432 Main Street, Woolworth Building, 1939, Commercial Art Deco438-440 Main Street, Washington Building, 1915, early 20th century Commercial62-70 Washington Street, Stueck's Modern Tavern, 1914, Renaissance Revival460 Main Street, Steuck's Block, 1893, Late 19th century Commercial472 Main Street, Penny Press Building; Alsop-King Building, 1873-4, Commercial Italianate476-478 Main Street, Pagan's New Block, 1912, Early Modern Commercial with Classical Revival detail484-494 Main Street, Caulkins & Post Building, 1889-1890, Commercial489-493 Main Street, Caulkin's Buick-Cadillac, 1905, Early 20th century Commercial501-507 Main Street, St. Aloysius Building, 1894, with 1916 Georgian Revival remodeling; a.k.a. St. Aloysius Society Building; collapsed 2 February 2011502-508 Main Street, Ward-Cody Building, 1880, Victorian Commercial, Birthplace of Major General Maurice Rose512-522 Main Street, J. Poliner & Sons, 1925, Colonial Revival533 Main Street, Central Fire Station, 1899, Renaissance Revival Fire Station530-540 Main Street, Palmer Building, 1900, Early 20th century Commercial542-544 Main Street, Southmayd's Building, 1872, Victorian Commercial with Classical detail546-548 Main Street, J. Poliner & Sons Shoe Store, 1833, 19th century Commercial560-564 Main Street, Lawton & Wall Block, 1867, Italianate Commercial unbroken common cornice with 566-576 Main Street and identical facade.566 Main Street, Lawton & Wall Block, 1870-1874574-576 Main Street, Lawton & Wall Block, 1870-1874, Italianate Commercial578-582 Main Street, 1894, Late 19th century Commercial584-588 Main Street, Shlien's Furniture, 1897, Commercial Italianate598-614 Main Street, Hotchkiss Block, Late 19th century Commercial9-11 Liberty Street, Mission Chapel, 1853, Greek Revival601-607 Main Street, Hotel Arrigoni, 1914, Colonial Revival613-617 Main Street, Scranton Building, 1876, Commercial Italianate630-636 Main Street, Spencer-Annenberg Block, 1897, 19th century Commercial625-631 Main Street, Arthur Magill, Jr. House-Chase School, 1821, Federal-Greek Revival635 Main Street, 1920, Early 20th century Commercial642-644 Main Street, Murphy's Drug Store, 1895, Commercial648-654 Main Street, Spencer Annenberg Block, 1870, addition 1911656-664 Main Street, 1898, Commercial666 Main Street, Stow Block, 1893, Commercial682-686 Main Street, Kabatznick Building, 1922, modern commercial with classical details695-699 Main Street, early 20th century Commercial696-700 Main Street, Applequest Block, 1898, Commercial Victorian710-712 Main Street, Fourth Meeting House of the First Church of Christ, Scientist, 1799, Federal style church716-724 Main Street, Early 20th century Commercial (no longer extant 2012)738 Main Street, O'Rourke's Diner, Early 20th century, erected on current site in 1947; Diner, Art Deco detailHartford Avenue, Riverview Cemetery, 1650-1850, dating from earliest settlement; much of it destroyed ca. 1950 for highway construction.St. John's Street, St. John's Cemetery, 1850–present, from earliest settlement of Irish immigrants; behind St. John's Roman Catholic Church. Notable for the extensive biographical information on the headstones, including birthplace in Ireland, family members and cause of death.5 St. John's Street, St. John's Parochial School, 1887, Victorian Institutional9 St. John's Street, St. John's Roman Catholic Church, 1852, spire-1864, Gothic Revival19 St. John's Street, St. John's Rectory, 1864, Second Empire33 St. John's Street, Catholic Charities Building, 1872, Victorian InstitutionalKing's Avenue, Trolley Barn, 1894, Late 19th century IndustrialThere are also 10 non-contributing properties in the district.
