Connecticut Juvenile Training School

The Town Farms Inn is a historic poor farm on Silver Street at River Road in Middletown, Connecticut. It was listed on the National Register of Historic Places in 1979. The poor farm provided employment and food for indigent people. (A similar town farm was operated in Hartford, on land now part of the Sigourney Square District.)There are two principal buildings. The older structure dates back to the late 1830s and is a 2+1⁄2-story, Federal style house built of brick. It measures 36 feet (11 m) by 34 feet (10 m). The exact date of construction is not known, but the date 1839 is carved into a flagstone in the front walk, and the style of construction is consistent with architecture in the late 1830s. The second building was built in 1891. It is also built of brick on brownstone foundations and measures 52 feet (16 m) by 34 feet (10 m). Between the two buildings, there were 14 rooms on the first floor, 29 rooms on the second, and three on the third floor. The back yard contains a long brick outbuilding, which is one story high and has a pitched roof. The total area of the nominated property is 4.3 acres (1.7 ha).The inn was originally built as a farmhouse by Thomas Griswold Mather, who married his first cousin Jane Ann Mather in 1834. His wife died in 1853, at which point he sold the farm and the buildings to the town of Middletown. At that time, there were 35 acres (14 ha) in the farm, with an additional 16 acres (6.5 ha) in a wood lot. The town operated it as a poor farm until 1946. By that time, town farms had been superseded by other social agencies. The town sold the property, and the new owners established a restaurant.

The Connecticut Valley Hospital Cemetery is a historic cemetery on Silvermine Road in Middletown, Connecticut. Founded in 1878, it served as the burying ground for patients of the Connecticut General Hospital for the Insane until 1957. Its design and layout are reflective of institutional cemetery practices of the period, with uniform numbered grave markers in a modestly landscaped setting. The cemetery was listed on the National Register of Historic Places in 1982.

WMRD (1150 AM) is a radio station licensed to serve Middletown, Connecticut, United States, broadcasting to the Hartford area. The station is owned by Crossroads Communications of Old Saybrook, LLC. It airs a talk and adult standards format.

Connecticut Valley Hospital in Middletown, Connecticut, is a public hospital operated by the state of Connecticut to treat people with mental illness. It was historically known as Connecticut General Hospital for the Insane. It is a 100-acre (40 ha) historic district that was listed on the National Register of Historic Places in 1985.The historic district includes late 19th and 20th century revival and late Victorian architecture. When listed on the National Register, the district included 27 contributing buildings. Also included were 25 non-contributing buildings.

Mansfield Club Grounds, also known as Mansfield Park and Fort Hill Grounds, was a baseball ballpark located in Middletown, Connecticut. The ballpark was home to the Middletown Mansfields baseball club during the 1872 season, from May 2nd until July 4th. Like the team, it was named after Civil War General Joseph K. Mansfield. The land for the ballpark, which overlooked Middletown, the Connecticut River, and the Valley Railroad, was donated in 1871 by Dewitt Clinton Sage who owned a nearby brick factory. The former site is now a residential development.

The Russell Company Upper Mill is an historic structure in Middletown, Connecticut, at the junction of Russell Street and East Main Street in South Farms, at the end of East Main Street's commercial and industrial development areas. Built in 1836, it is listed on the National Register of Historic Places. There is a small pond to the south. Small businesses border the street to the north, followed by the buildings of Russell Manufacturing Company, the area's most dominant feature. Russell Street crosses Sumner Brook nearby and ascends to a large residential district to the west. The mill is currently a condo-apartment complex.

The Sanseer Mill is a historic 19th-century mill at 282 Main Street Extension in Middletown, Connecticut. It was added to the United States National Register of Historic Places in 1986.

The Marlborough Street Historic District encompasses one of the finest collections of 19th-century residential architecture in Portland, Connecticut. Extending along Marlborough Street (Connecticut Route 66) east of Main Street, it includes twelve houses built between 1847 and 1900 in a variety of architectural styles. The district was listed on the National Register of Historic Places in 1983.

Middlesex Community College (Middlesex and MxCC) is a public community college in Middletown, Connecticut, United States. It is part of the Connecticut State Colleges & Universities system (CSCU). The college has an open admissions policy. MxCC has about 4,400 full- and part-time students enrolled. It is a commuter school with no dormitories. MxCC offers associate degrees, certificates, and specialist programs.

The Middletown, Connecticut Christopher Columbus statue was a memorial to Columbus that was installed in the city's Harbor Park. The sculpture was donated to the city in 1996 by the Italian American Civic Order, the Italian Society of Middletown and local Italian-American families.The statue has been repeatedly vandalized. In 2016 the test on its plinth, reading "discoverer of America" was changed to "looter of America". It was damaged in 2017 when vandals chipped away the sculpture's nose. Also in 2017, vandals painted the statue's hands in red, and left the spray-painted text "kill the colonizer" on the statue's base. In 2019 it was vandalized again with red spray-paint.The statue was removed in June 2020.

Xavier High School is an all-boys college preparatory Catholic high school in Middletown, Connecticut, United States. It is run by the Xaverian Brothers. Teenage boys from over 65 towns surrounding and including Middletown attend Xavier; despite the fact that students commute from a very broad area all students, their parents, faculty, and staff, regardless of how far away they live from the school, are referred to by Xavier officials as "The Xavier Community".Mercy High School, Xavier's all-girls sister school, is located down the street 3 miles (4.8 km) away from Xavier. Xavier is sponsored jointly by the Roman Catholic Diocese of Norwich and the Congregation of the Brothers of Saint Francis Xavier. The school was incorporated under the laws of the State of Connecticut on February 18, 1963.

Elmcrest Hospital, later St. Francis Care Behavioral Health, was a small psychiatric facility in Portland, Connecticut. Opened in 1942, the campus incorporated three historic mansions, including a childhood home of 1800s businesswoman Elizabeth Jarvis Colt. The facility was purchased by Saint Francis Hospital in 1997, and in 1998, the hospital underwent increased scrutiny when an 11-year-old patient died while being restrained by an employee. In 2003, inpatient services at the campus were discontinued, and patients were relocated to the Saint Francis Mount Sinai campus. Hartford Hospital purchased the campus in 2003 and continued operating the outpatient and partial hospitalization services for children and teens at the site through its affiliate the Rushford Center. Rushford discontinued operations at the site c. 2006. A redevelopment plan that would have demolished two of the three historic homes was proposed in 2006, however the original effort had stalled by 2009. On February 1, 2018, the Portland Planning and Zoning Commission voted unanimously to approve the Brainerd Place development for the site. As of 2022, the project is expected to include a mix of apartments and retail, while adaptively redeveloping the three historic homes in place.