Statue of Christopher Columbus (Middletown, Connecticut)

The Metro South Historic District encompasses a portion of the downtown area of Middletown, Connecticut. Extending south from Main and College Streets for two blocks, this area was developed in the 19th century, and contains a diversity of well-preserved architecture from that period, some with association to locally important individuals. It was listed on the National Register of Historic Places in 1980.

The Main Street Historic District encompasses the historic commercial center of Middletown, Connecticut, United States. Middletown was one of the most important ports on the Connecticut River during 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.

Middlesex Hospital is a non-profit, acute care community hospital in Middletown, Connecticut. Its service area includes Middlesex County, Connecticut, and the lower Connecticut River Valley region. In 2015 Middlesex became the first hospital in Connecticut to join the Mayo Clinic Care Network.

The Captain Benjamin Williams House, also known as deKoven House or DeKoven Community Center, is a historic house at 27 Washington Street in Middletown, Connecticut. Built in the late 18th century, it is a particularly fine example of late Georgian architecture, and was listed on the National Register of Historic Places in 1978. It is now owned and operated by the Rockfall Foundation and operated as a community center.

Located in Middletown, Connecticut, the Middletown South Green Historic District was created to preserved the historic character of the city's South Green and the historic buildings that surround it. It is a 90-acre (36 ha) historic district that includes a concentration of predominantly residential high-quality architecture from the late 19th century. It was listed on the National Register of Historic Places in 1975.

The Old Middletown Post Office, in Middletown, Connecticut, also known as the U.S. Post Office, was built in 1916. It was listed on the National Register of Historic Places (NRHP) in 1982. The building is also on the NRHP as a contributing property of the Main Street Historic District.

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 Broad Street Historic District encompasses a well-preserved 19th-century residential area in Middletown, Connecticut, USA. Centered on Broad and Pearl Streets west of Main Street, the area was developed residential in response to local economic development intended to revitalize the city, whose port was in decline. The district includes the city's largest concentration of Greek Revival houses, and was listed on the National Register of Historic Places in 1988.

St. Mary of Czestochowa Parish (Polish: Parafia św. Marii Częstochowskiej w Middletown) is a Catholic church parish in Middletown, Connecticut that was founded for Polish immigrants. The St. Mary of Czestochowa Church is a church building at 79 South Main Street in Middletown. The parish was founded in 1903. It is one of the Polish-American Roman Catholic parishes in New England in the Roman Catholic Diocese of Norwich.

Middletown is a city in Middlesex County, Connecticut, United States. Located along the Connecticut River, in the central part of the state, it is 16 miles (26 kilometers) south of Hartford. Middletown is the largest city in the Lower Connecticut River Valley Planning Region. In 1650, it was incorporated by English settlers as a town under its original Native American name, Mattabeseck, after the local Wangunk village of the same name. They were among many tribes along the Atlantic coast who spoke Algonquian languages. The colonists renamed the settlement in 1653. When Hartford County was organized on May 10, 1666, Middletown was included within its boundaries. In 1784, the central settlement was incorporated as a city distinct from the town. Both were included within newly formed Middlesex County in May 1785. In 1923, the City of Middletown was consolidated with the Town, making the city limits extensive. Originally developed as a sailing port and then an industrial center on the Connecticut River, it is now largely residential. Its downtown, based on Main Street, serves as a popular retail, dining, and bar district near Wesleyan University. Middletown was the county seat of Middlesex County from its creation in 1785 until the elimination of county government in 1960. As of the 2020 census, the city had a total population of 47,717. Middletown, Connecticut is considered the southernmost city in the Hartford-Springfield Knowledge Corridor Metropolitan Region, which features a combined metro population of 1.9 million. Middletown is largely a politically progressive city, and is home to one of the largest pride events in all of Connecticut.

The Church of the Holy Trinity is an historic Episcopal church at 381 Main Street in Middletown, Connecticut. Completed in 1874, it is one of the city's finest examples of Gothic Revival architecture. Its nearby former rectory, also known as the Bishop Acheson House, is one of its finest Colonial Revival houses. The two buildings were listed on the National Register of Historic Places in 1979.

The Middletown–Portland railroad bridge is a swing truss railroad bridge crossing the Connecticut River and Route 9 in Middletown, Connecticut, just south of the Arrigoni Bridge. The bridge is a Warren through-truss swing bridge with an overall length of 1,142 ft (348 m) and a rotating center span. It is used by the Providence and Worcester Railroad to serve freight customers in Portland.The first rail bridge at the site was constructed by the Boston and New York Air-Line Railroad in 1873. It was replaced by the current bridge in 1911. The bridge was featured prominently in the video for the 1993 Billy Joel hit "The River of Dreams".