Arrigoni Bridge

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".

The Mattabesset River as delineated on present-day maps flows out of Harts Ponds in the town of Berlin and travels 16.1 miles (25.9 km) east to the Connecticut River, passing Kensington and later forming the boundary between Middletown and Cromwell.Further south, the Coginchaug River (or "winding meadow") flows from an upland meadow in Durham, northwards to the Mattabesset just upstream of that river's junction with the Connecticut. This river was the route to the portage place, located near Palmer Field, just below Sowheag's main stronghold at Indian Hill. Since it was the old western boundary of the incorporated City of Middletown, it was also called the West River, and also, for no known reasons, it was given other names, including the Sebethe River and the Arrawanna River. Presumably the word Mattabeseck was never considered properly euphonious, and various local individuals tried to improve on the name poetically.

O'Rourke's Diner is a diner located in the Main Street Historic District in Middletown, Connecticut.

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.

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.

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.

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 Portland Brownstone Quarries are a set of historic quarries in Portland, Connecticut. The brownstone mined from these quarries was an important source for construction in the latter half of the 19th century. The stone from these quarries was used in a number of landmark buildings in Chicago, Boston, New York City, Philadelphia, Baltimore, Washington, D.C., New Haven, Connecticut, and Hartford. The site was listed as a National Historic Landmark, which also placed it on the National Register of Historic Places, on May 16, 2000.

Portland is a town in Middlesex County, Connecticut, United States. The town is part of the Lower Connecticut River Valley Planning Region. The population was 9,384 at the 2020 census. The town center is listed as a census-designated place (CDP). It is situated across the Connecticut River from Middletown. Brownstone quarried in Portland was used in the construction of Hartford's Old State House in 1796. The vast majority of the brownstone buildings in Connecticut (see College Row at Wesleyan University and the Long Walk at Trinity College) as well as the famous brownstones in New York City were built with brownstone from Portland's quarries. Later, one of the quarries was transformed into an adventure park in the summer months featuring zip lines, cliff diving and scuba locations. About half of the town's perimeter is made up of the Connecticut River. The town has eight marinas and boat clubs as well as three 18-hole golf courses.

Saint Sebastian is a Roman Catholic church in Middletown, Connecticut, part of the Diocese of Norwich.

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.

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.