O'Rourke's Diner

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.

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

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.

St. Luke's Home for Destitute and Aged Women was incorporated by an act of the Connecticut State Assembly on June 22, 1865. For twenty-seven years the home was conducted in an old house on the southwest corner of Court and Pearl Street. in 1892 a large legacy enabled a new home to be erected at the present site at Pearl and Lincoln Streets. Comfortable quarters are provided for fourteen women. Members of the Church of the Holy Trinity played a large part in establishing the endowment; frequently the current rector of that church serves as president of the Board of Trustees. The substantial brick building looks like a carefully designed apartment house, rather than an institution. At three-and-a-half stories tall, the first floor is partly below ground level. A long run of brownstone steps leads to a center entrance door on the second floor level. Two bay window piers flank the front entrance, capped off above the roof line by gable-roofed dormers. Decorative elements such as the wrought iron fence, ivy on the facade, and quoin-like brick projections on all corners add a picturesque quality to the building.The large brick institutional building dominates the area by its mass and corner siting at Pearl and Lincoln Streets in Middletown's residential North End. It forms a dividing line between large structures to the south towards Washington Street and more modest late Victorian era worker homes to the north.

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".

Russell Library is an 1876 library located at 123 Broad Street in Middletown, Connecticut.

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.

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 Samuel Russell House is a neoclassical house at 350 High Street in Middletown, Connecticut, built in 1828 to a design by architect Ithiel Town. Many architectural historians consider it to be one of the finest Greek Revival mansions in the northeastern United States. Town's client was Samuel Russell (1789-1862), the founder of Russell & Company, the largest and most important American firm to do business in the China trade in the 19th century, and whose fortunes were primarily based on smuggling illegal and addictive opium into China. The house was listed on the National Register of Historic Places in 1970, and designated as a National Historic Landmark in 2001. It has been owned by Wesleyan University since 1937 and now houses the Department of Philosophy.

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.