Seth Wetmore House

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 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.

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.

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.

The Plumb House is a historic house at 872 Westfield Street in Middletown, Connecticut, USA. It was built in 1804 by James Plumb, and is exceptionally well preserved. It was listed on the National Register of Historic Places in 1978. The house is built with clapboard sidings, a brownstone foundation and an asphalt shingle roof. It has a wood frame, with post and beam construction and a hip roof. The architect and builder are unknown. Historically and currently it has been a private residence.

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.

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

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.

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.

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