The land on the western bank of the Connecticut River where Middletown now lies was home to a village of the
Wangunk, a tribe of
Algonquian-speaking
Native Americans. The village was named
Mattabesset (also spelled
Mattabesett, Mattabesec, Mattabeseck, and
Mattabesek); the area they inhabited—now Middletown and the surrounding area—was named after it. When the primarily English European settlers arrived in the region the Mattabesset were a part of the Wangunk, a large tribe in the Connecticut Valley, at the time under a sachem named Sowheag. Plans for the colonial settlement were drawn up by the General Court in 1646; the first migrants came from nearby Connecticut colonies in 1650. On September 11, 1651, the General Court of Connecticut established the town of "Mattabesett". A couple of years later in November 1653, the settlement was renamed as Middletown. This name was chosen because the site was approximately halfway between Windsor and
Saybrook on the Great River. Life was not easy for these early colonial
Puritans; clearing the land and building houses, and tending farms in the rocky soil of New England was a labor-intensive ordeal. They had a strict society; offenses legally punishable by death in the Connecticut colonies included "witchcraft, blasphemy, cursing or smiting of parents, and incorrigible stubbornness of children." During the 18th century, Middletown became the largest and most prosperous settlement in Connecticut. By the time of the
American Revolution, Middletown was a thriving port, where one-third of its residents were involved in merchant and maritime activities. Some settlers held enslaved Africans as workers in the early economy of Middletown; they worked as domestic servants, laborers, and in shipping.
African slaves were imported by the English in 1661 from
Barbados in the Caribbean. By 1756 Middletown had the third-largest African slave population in the state of Connecticut—218 slaves to 5,446 whites. During the mid-19th century, manufacturing replaced trade as Middletown's economic mainstay. But industrial growth was limited after railroad operators bypassed Middletown in their construction of a railway between Hartford and New Haven. There had been an ambitious plan to build a railroad
suspension bridge from White Rock in Middletown to Bodkin Rock in Portland vicinity, which was seen as an unpractical solution. Middletownians played an active role in the American Civil War. General
Joseph K. Mansfield was a Union general at the
Battle of Antietam, where he died in action in 1862. Another casualty at Antietam was Brigadier General
George Taylor, who had been educated at a private military academy in Middletown. The popular Civil War marching song "
Marching Through Georgia" was written by
Henry Clay Work, a Middletown resident. Some residents were active in the
abolitionism movement, and the city was a hub along the
Underground Railroad. The Connecticut General Hospital for the Insane was opened in Middletown in 1868. It was the first public mental healthcare facility in Connecticut, which up until that time was in a minority of states which did not support public insane asylums. By 1896, four groups of buildings had been erected on Connecticut General Hospital for the Insane's site in the South Farm district, and the institution was one of the largest of its kind in the country. It is associated with
Connecticut Valley Hospital Cemetery. As of 2025, the institution has been renamed
Connecticut Valley Hospital, and administers psychiatric care through the Department of Mental Health and Addiction Services. It remains one of Middletown's top employers. In the latter half of the 19th century, manufacturing was the mainstay of the city's economy, especially finely made metal parts, such as marine hardware (Wilcox, Crittendon & Co.) and typewriters (Royal Typewriters). There were also several machine tool and die manufacturers in the city. Middletown was the site of a major unit of
Goodyear. In addition, there was the pioneer
automobile manufacturer
Eisenhuth Horseless Vehicle Company. Other manufacturers included in national expositions and now museum collections include the Middletown Plate Company (silver), Middletown Silver Co. and I. E. Palmer (hammocks). Middletown also briefly was the home of a major-league baseball team, the
Middletown Mansfields of the
National Association. In the late 19th and early 20th century, the city underwent a demographic transformation, after having been settled primarily by Protestant people from the British Isles. First the Irish, in response to the
Great Famine, and then large numbers of Italian immigrants arrived to work in Middletown's factories and farms. Many of the Italians were immigrants from
Melilli,
Sicily. Both groups were primarily Roman Catholic. Polish and German arrivals followed, and many of these immigrants were also Catholic. By 1910 the population had swelled to nearly 21,000. Meanwhile, the number of African Americans dwindled to 53 persons. Employers chose to hire white immigrants. Later in the century, more African Americans from the South migrated to the area for its industrial jobs and better social conditions. They were part of the
Great Migration during the 20th century, up to 1970. In the early 1980s, two Wesleyan professors arranged to bring a small group of
Cambodian refugees to Middletown, who were exiled following the US involvement in Southeast Asia in the
Vietnam War. They developed a thriving Cambodian community, as have later migrants from
Tibet. Middletown also attracted
Hindu immigrants from
India and other parts of Southeast Asia, who established the first Hindu temple in Connecticut in Middletown. Over the decades the new immigrants stimulated the rise of a range of cuisines offered by restaurants. This has become one of the most well-known aspects of the city. Middletown was hit by floods in 1927 and 1936, and by
The Great New England Hurricane in 1938. The
Arrigoni Bridge was completed over the Connecticut River in 1938. It replaced an earlier bridge to connect Middletown to
Portland and points east. During the 1950s, as the prevalence of the automobile increased, government officials approved the construction of a highway that effectively separated Middletown from the Connecticut River, which had long supported its development. Highway construction demolished historic neighborhoods, including many buildings from the 18th century. New suburban developments were built outside older neighborhoods, attracting the people with money to buy new. In the mid-20th century, Middletown and similar towns lost heavy industry and manufacturing jobs that moved offshore, resulting in a general decline in population. An alternate economy began to develop by the 1990s. During this period, the city tore down many older buildings in the name of '
urban renewal', but sometimes new development was delayed for years. Downtown area had large flat parking lots, or buildings were abandoned and left empty. With high unemployment and limited opportunities, and increasing problems with drugs, crime increased. During the 1960s,
Pratt & Whitney opened a large aircraft engine plant in the Maromas section of Middletown. Concurrently, developers bought much of the city's remaining farms, including most of Oak Grove Dairy, to redevelop as residential suburbs for local workers and commuters to surrounding cities. During the 1970s,
Oddfellows Playhouse was established. The theater attracts hundreds of young people every year from around the state to perform in plays and other performances. The playhouse is one of the few youth theaters in the state of
Connecticut. It is located on 128 Washington Street, around the corner from Middletown's Main Street. During the 1990s, a partnership between the city, the Middlesex Chamber of Commerce, and Wesleyan University invested substantially in Middletown's Main Street, improving urban design and supporting new businesses. Their actions helped the revival of downtown Middletown. Crime decreased, and new restaurants and shops opened.
21st century In recent decades, Middletown has focused on balancing the needs and comforts of its residents with the commercial development required to help fund services. These efforts date at least from 1931, when the city was one of the first in America to establish a planning board. Progress continued under the leadership of Democratic mayor, Domenique S. Thornton, who served a record eight years (four terms) as mayor. The city attracted a 12-screen movie theater and numerous restaurants and other businesses to the downtown area, the city provided free
Wi-Fi service along Main Street and the historic Inn at Middletown a luxury four and half star boutique hotel transformed the former vacant National Guard Armory. On November 8, 2005, Republican
Sebastian Giuliano won the mayor's office, replacing Thornton, whom he criticized for raising taxes and for the awarding of a contract for the construction of a new high school to
Tomasso Brothers, Inc., a firm that had been the target of a federal corruption probe. During Giuliano's three terms in office, Middletown's Main Street became a hub for small businesses, and the city began investing heavily in the arts. Democrat Daniel T. Drew defeated Giuliano in 2011. Drew has pushed for increased development in the city's North End, an area that has been plagued by poverty and crime in recent decades. In November 2012, voters approved a $37 (~$ in ) Million initiative to move Middletown's wastewater to the Mattabassett Sewer District treatment plant in nearby
Cromwell. Previously, the city had operated its own sewage treatment plant on the banks of the
Connecticut River. The city has made plans to tear down this older plant and develop the riverfront property on which it sits. Middletown continues to support manufacturing and small business. Middletown has remained an important government administrative center. From the creation of Middlesex County in 1798 until the elimination of county government in 1965 Middletown was the county seat. Middletown today retains Middlesex Superior Court, and the Judicial District remains that of the former county court. Other county functions were either centralized to the state or transferred to the towns. The former county building has been removed, but there are other state agency buildings elsewhere in the city, such as the Dept. of Social Services on Main Street Ext. Middletown's Probate Court district includes the towns of Cromwell, Portland, Middlefield and Haddam. The city is also the site of the controversial State Juvenile Training Center. Culturally and politically, Middletown is in the midst of an effort to revitalize its historically disadvantaged North End. Economic development projects recently completed in the North End include Wharfside Commons, a 96-unit mixed income apartment block, and the new Community Health Center (completed in 2012 at the corner of Main and Grand Streets). The Green Street Arts Center, founded by Wesleyan and a coalition of community groups in 2000, is a pioneering attempt to attract residents and businesses to the neighborhood by promoting arts education and outreach. For decades, the famous
O'Rourke's Diner has done much to bring some stability to the North End. A fire on August 31, 2006, gutted much of the historic structure. The Middletown community held many fundraising events to raise money for the diner's rebuilding. Reconstruction began in September 2007, and
O'Rourke's Diner re-opened in February 2008.
Mayor Daniel Drew (2011–2019) supported citizen-oriented efforts to revitalize the North End, such as the local nonprofit NEAT (North End Action Team). In 2012, the City of Middletown and NEAT partnered to form the "I Heart the North End" initiative, which plans to raise public awareness of the economic and cultural opportunities available in the area. Middletown is the only location of a well-known youth theater group,
Oddfellows Playhouse, which is located on Washington Street and pulls in children of all ages from all over the state to learn theater skills. Oddfellows also runs the Children's Circus of Middletown where children learn circus skills and put on a free show for close to a thousand people. Middletown is also host to the Kidcity Children's Museum located in a renovated and recently expanded former home of Judge Elmer, which was moved down Washington Street to its current location. Kidcity is a hands-on playspace where children ages 1 through 8 come with parents and other significant adults to learn through play. The Downtown Business District continues to revitalize the downtown area.
Pratt and Whitney, Aetna, Middlesex Hospital,
Connecticut Valley Hospital,
Liberty Bank, and
Wesleyan University are major employers. Located on the western border of the city, in an area known as Westlake, is an 84 house community known as The Farms. This architectural award-winning community was developed in 1969 by George Achenbach, and was one of the first communities in Connecticut designed for
cluster living, with open areas designated as
common land. There are also many parks and nature trails including the
Middletown Nature Gardens, Wadsworth Falls State Park and
Smith Park, and of open property at the Guida Farm Conservation Area for families to enjoy. Harbor Park is a recreation area on the Connecticut River, featuring a boardwalk, restaurant/nightclub, fishing, seasonal boat excursions, and the Middletown High School and Wesleyan University crew boathouses. July 4 festivities, as well as the head of the Connecticut Regatta event in October are conducted from Harbor Park. Middlesex Hospital a major employer in Middletown and throughout Middlesex County, is spending $31 million to build a new emergency department. The new
emergency department opened on March 24, 2008. Along with the new department, a helipad will be added along with 70 new parking spaces for patients. At 11:17 a.m. on February 7, 2010, a large explosion occurred at a
power plant under construction in Middletown.There are numerous
houses, buildings and historic districts in Middletown listed on the National Register of Historic Places, and two are further designated as
National Historic Landmarks. The
Samuel Wadsworth Russell House on High Street, built in 1827, was declared a National Historic Landmark in 2001. The
Alsop House, also located on High Street, and built in 1840, was designated a National Historic Landmark in 2009. Both buildings are part of the Wesleyan campus. The
saltbox Samuel Harris House, built in 1686 and not listed on the National Register, may be the oldest surviving house in Middletown. ==Geography==