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.

[4] 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 Algongquian-speaking Native Americans.

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.

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.

"[5][6] The Pequot Mohegan, at that time traditional allies of the English colonists and enemies of the Wangunk, arrived in the Middletown area in the latter half of the 17th century; conflict between them and local Native American tribes ensued.

Records show that, over time, Sowheag was forced to sell off most of Mattabesett to the local colonists; by 1676 the Puritans owned all but 300 acres (1.2 km2) of the former territory.

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.

[6] Middletown merchant traders pushed for the clearance of the Saybrook Bar at the mouth of the Connecticut River, and later sought the creation of Middlesex County in 1785.

The same persons also established the Middlesex Turnpike (now Route 154) to link all the settlements on the western side of the Connecticut, again with the intent of creating one long port.

The port's decline began in the early 19th century during the period of strained American-British relations and resulting trade restrictions, which led to the War of 1812.

The city's men distinguished themselves in the war effort, as Middletown's Commodore Thomas Macdonough led American forces to the victory on Lake Champlain in 1814 which ended British hopes for an invasion of New York.

The two main buildings of the original campus were built by the people of Middletown in order to attract an academic institution to the city.

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.

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.

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.

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.

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.

In recent decades, Middletown has focused on balancing the needs and comforts of its residents with the commercial development required to help fund services.

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.

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 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.

Harbor Park is a 2.6-acre (11,000 m2) 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.

Middletown shares borders with the neighboring towns of Cromwell, Portland, East Hampton, Haddam, Durham, Middlefield, Berlin, and Meriden.

Of all the neighboring towns, Portland and East Hampton are the only ones that do not have any land boundaries, as they are located on the eastern side of the Connecticut River.

The west side of Middletown is flanked by the Metacomet Ridge—a mountainous trap rock ridgeline that stretches from Long Island Sound to nearly the Vermont border.

Middletown's riverfront and bridges were featured extensively in the music video for Billy Joel's hit song "The River of Dreams".