Harriet Cooper Lane House

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.

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

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.

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.

The Starr Mill Road Bridge is a historic bridge in Middletown, Connecticut. It is a single span Warren through truss bridge, spanning the Coginchaug River near the Starr Mill complex on the west bank of the river. Built in 1927 by the Berlin Construction Company, it is one of a shrinking number of period metal truss bridges in the state. The bridge was listed on the National Register of Historic Places in 1993. It is closed to all forms of passage.

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 Middletown Nature Gardens is located off Randolph Road in Middletown, Connecticut. In 1995, the city of Middletown, CT purchased the 18 acres (73,000 m2) of land and dedicated it open space. This piece of land serves as a natural habitat to many plants and animals. There are many trails to walk about surrounded by an array of diverse trees and shrubs. Some of the types of trees and shrubs include red cedar, flowering dogwood, highbush blueberries, white pine, and speckled alder. The main trail is a 0.5-mile (0.80 km) loop. Mulched side trails, which branch off the main trail, add another 0.5 miles (0.80 km) to walk. Community volunteers maintain the park. They have erected many bluebird boxes and bat houses to house some of the natural wildlife of the park. There are also vernal pools, which are habitats for salamanders and wood frogs in the southeast corner of the park. There is even a 200-year-old sugar maple, which is called the “bee tree,” in which a large colony of bees has made it their home.

Wadsworth Falls State Park, or simply Wadsworth Falls, is a public recreation and preserved natural area located on the Coginchaug River in the towns of Middletown and Middlefield, Connecticut. The state park's 285 acres (115 ha) offer trail hiking and fishing. Swimming and picnicking are allowed at the pond near the north entrance near 721 Wadsworth Street (CT Route 157) in Middletown. It is managed by the Connecticut Department of Energy and Environmental Protection.

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.

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.

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.

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