Terry's Plain Historic District

Westminster School is a private, coeducational college-preparatory, boarding and day school located in Simsbury, Connecticut accepting around 20% of applicants. The total student population is approximately 400, and includes pupils from 25 US states and 30 countries. It is also a member of the Founders League, an athletic league comprising ten college preparatory boarding schools in Connecticut and one in New York.

The Horace Belden School and Central Grammar School are a pair of architecturally distinguished Late Gothic Revival occupying a single campus at 933 Hopmeadow Street and 29 Massaco Street in Simsbury, Connecticut. The Belden School was built in 1907 as the first Simsbury High School, and now serves as Simsbury Town Hall. The Central Grammar School, built in 1913, is now called the Central School. The buildings were listed as a pair on the National Register of Historic Places in 1993 for their architecture and their role in the town's educational system.

Hendrick Cottage is a historic building in Simsbury, Connecticut, United States. Dating to around 1795, it is believed to have been built by John Poisson. In 1965, it was moved half a mile from its original location (on the north bank of Hop Brook facing West Street) to become part of the collection of nine buildings comprising the Massacoh Plantation, part of Simsbury Center Historic District. It is named for its last owner, Fanny Josephine Pomeroy Hendrick.The building is listed on the National Register of Historic Places.

The Captain Elisha Phelps House is a historic house museum at 800 Hopmeadow Street in Simsbury, Connecticut. The colonial-era house was built by David Phelps in 1711. His son Elisha Phelps received the land from his father and expanded the house in 1771. Elisha Phelps along with his brother Noah Phelps and others took part in the capture of Fort Ticonderoga in 1775. Capt. Phelps was appointed as commissary of the Northern Department by the Continental Congress.The house was used as a hotel named the Canal Hotel, after the War of 1812. It is located along what was the New Haven and Northampton Canal line.

Simsbury station is a former railroad station in the center of Simsbury, Connecticut. Built in 1875, it is a distinctive example of a railroad station with Italianate styling. The building was listed on the National Register of Historic Places on March 26, 1976 as Simsbury Railroad Depot. Presently, it houses a restaurant, called "Plan B".

The Simsbury Bank and Trust Company Building, also known as the former Town Hall Building, is a historic commercial and civic building at 760 Hopmeadow Street in Simsbury, Connecticut. Built in 1917, it is a prominent local example of Colonial Revival architecture with Beaux Arts features. It originally housed the town's first bank, and was its town hall between 1969 and 1984. The building was listed on the National Register of Historic Places in 1986.

Eno Memorial Hall is a historic civic building at 754 Hopmeadow Street in Simsbury, Connecticut. Built in 1932, it served historically as a courthouse, as a city hall, as an auditorium, and as government offices. It was designed by Roy D. Bassette, and was given to the town by Antoinette Eno Wood, who was descended from some of the town's early settlers. It presently serves as the town's senior center. The hall was listed on the National Register of Historic Places in 1993.

The Simsbury Center Historic District is a 75-acre (30 ha) historic district located in the town center area of Simsbury, Connecticut. It encompasses seven blocks of Hopmeadow Street, as well as the cluster of commercial, civic, and residential buildings along Railroad, Station, and Wilcox Streets, and Phelps Lane. Although its oldest element is the cemetery (established 1688), most of its buildings were built in the late 19th and early 20th century. It was listed on the National Register of Historic Places in 1996.: 2 

The Amos Eno House, also known as the Simsbury 1820 House, is a historic home at 731 Hopmeadow Street in Simsbury, Connecticut.

The Robert and Julia Darling House, now the Cannon Building, is a historic house at 728 Hopmeadow Street in Simsbury, Connecticut. Built in 1927 for a local business leader, it is one of the town's largest and most distinctive examples of Colonial Revival architecture. The house was listed on the National Register of Historic Places in 1991. It now houses professional offices.

Drake Hill Road Bridge, also known as the Old Drake Hill Flower Bridge, is a bridge in Simsbury, Connecticut, originally carrying Drake Hill Road over the Farmington River. Built in 1892, it is one of three surviving Parker truss bridges in the state. It was listed on the National Register of Historic Places in 1984. It now carries foot traffic only.

Penwood State Park is a public recreation area located on Talcott Mountain in the town of Bloomfield, Connecticut. The state park's 787 acres (318 ha) are contiguous with the north end of Talcott Mountain State Park. Both parks are managed by the Connecticut Department of Energy and Environmental Protection.