Williams and Stancliff Octagon Houses

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.

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.

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.

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 census-designated place (CDP) comprising the primary village and adjacent residential land in the town of Portland, Middlesex County, Connecticut, United States. It is in the southwest part of the town, bordered to the west and south by the Connecticut River, which forms the border with Cromwell to the west and Middletown to the south. The Portland CDP extends north along Main Street (Connecticut Route 17A) to its junction with Gospel Lane (Connecticut Route 17) at Fogelmarks Corners, and the eastern extent of the CDP is at Rose Hill Road and Collins Hill Road. The CDP includes the neighborhood of Gildersleeve in the north. As of the 2020 census, the CDP had a population of 5,813, out of 9,384 in the entire town of Portland.

The Arrigoni Bridge, also known locally as the Portland Bridge is a steel through arch bridge carrying Route 66 and Route 17 across the Connecticut River, connecting Middletown, Connecticut, to Portland, Connecticut. When it opened in 1938, the 1,200 feet (370 m) bridge was the most expensive bridge ever built in Connecticut, at a cost of $3.5 million. Its two distinctive 600 feet (180 m) steel arches have the longest span length of any bridge in the state. The bridge has an average daily traffic of 33,600.It was named after state legislator Charles J. Arrigoni, who promoted the project. Arrigoni served in the Connecticut House of Representatives from 1933 to 1936 and in the Connecticut State Senate from 1937 to 1940.

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.

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 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 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.

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