Starr Mill Road Bridge

Two 19th century factory buildings are sited on a bank beside Starr Mill pond on Beverly Heights just off Middlefield Street. Each building is 3½ stories tall, and overlooks a picturesque pond and woods to the west; a parking lot packed with trucks and industrial equipment on the south; and nineteenth century housing on Beverly Heights to the north.

The Wadsworth Mansion at Long Hill Estate is located at 421 Wadsworth Street in Middletown, Connecticut. It is a 16,000-square-foot (1,500 m2) classical revival house situated on 103 acres (0.42 km2) wooded area. It is currently owned by the City of Middletown and is operated by the Long Hill Estate Authority. The mansion is the centerpiece of the Wadsworth Estate Historic District of 270 acres (1.1 km2), which includes the mansion's associated outbuildings, the Middletown portion of Wadsworth Falls State Park, the Nehemiah Hubbard House, and several barns and farmhouses along Laurel Grove Road such as the Harriet Cooper Lane House.

Palmer Field is a multi-use baseball, soccer, and football stadium located in Middletown, Connecticut. In 1993 and 1994, the first two editions of the Ivy League Baseball Championship Series were held at the field, with Yale claiming both titles.

The Nehemiah Hubbard House is a historic house at the corner of Laurel Grove and Wadsworth Street, Middletown, Connecticut. Built in 1745, it is a center-chimney colonial style house built of clapboard siding and brownstone foundation with wood shingle roof; using a structural system of wood frame, post and beam with gable roof. It was built as a residence which is its current use.

Address: 30 Laurel Grove Road, Middletown, Connecticut Style: Center-Chimney Colonial Date of Construction: 1741 Materials: Clapboard and Brownstone Foundation with Wood shingle roof Structural System: Wood frame and Post and Beam Architect: Unknown Builder: Unknown Historic Use: Residence Present Use: Residence

The Seth Wetmore House is a residence built in the Center-Hall Colonial style in 1746 at 1066 Washington Street, Middletown, Connecticut. It was built of Clapboard siding, Brownstone foundation with asphalt shingle roof using a structural system of wood frame, post and beam with gable roof. It was added to the National Register of Historic Places on September 10, 1970.

Long Lane School was a prison for juvenile inmates in Middletown, Connecticut. Historically a prison for delinquent girls, it underwent various name changes, was acquired by the state in 1924, and began housing boys in 1972. Prior to its 2003 closure, it was operated by the Connecticut Department of Children and Families, and was for inmates of the ages 11–16. It was a locked and high-security facility. In its lifetime, Long Lane remained unfenced.

Indian Hill Cemetery is a historic rural cemetery located at 383 Washington Street in Middletown, Connecticut on a hill adjacent to Wesleyan University.

Mercy High School is a private, Roman Catholic, all-girls high school in Middletown, Connecticut located within the Roman Catholic Diocese of Norwich.

The Arrawanna Bridge is a historic bridge, spanning the Coginchaug River near Berlin Street in Middletown, Connecticut, USA. Built in 1918, it is an early example in the state of an open-spandrel concrete arch bridge, and is one of the state's oldest bridges. It was listed on the National Register of Historic Places in 2004. The bridge is now closed to all traffic.

WESU is a college/community non-commercial FM radio station owned by Wesleyan University and licensed to Middletown, Connecticut.

Vinal Technical High School, or Vinal Tech, is a technical high school located in Middletown, Connecticut. It is in the Connecticut Technical Education and Career System. It receives students from many nearby towns. Vinal Tech currently has around 600 students from approximately 27 different towns.