Penwood State Park

The John Humphrey House is a historic house at 115 East Weatogue Street in Simsbury, Connecticut. Built about 1760, it is a well-preserved example of a Georgian colonial residence. It was listed on the National Register of Historic Places in 1990.

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.

The Terry's Plain Historic District is a 325-acre (132 ha) historic district in the town of Simsbury, Connecticut that was listed on the National Register of Historic Places in 1993. The district is significant as a preserved rural landscape. It included 27 contributing buildings of various architectural styles, including Greek Revival, Federal and Late Victorian architecture, and 17 non-contributing buildings. Thirteen houses that were parts of farm complexes and 14 agricultural outbuildings ranging from sheds to large tobacco barns.Contributing sites include: A field where the militia drilled in 1683 (or 1685) 24 Ferry Lane, barn from c. 1840, house non-contributing (see #2 in photos accompanying NRHP nomination): 7  Lucius D. Goodrich House, 36 Ferry Lane, c. 1836, Federal/Greek Revival: 7  64 Terry's Plain Road, Late Victorian: 8 

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 East Weatogue Historic District is a 490-acre (200 ha) historic district in the town of Simsbury, Connecticut that was listed on the National Register of Historic Places in 1990. It then included 102 contributing buildings, 10 contributing sites, 11 contributing structures, and one other contributing object. The district encompasses a largely agrarian rural village centered at the junction of Hartford Road and East Weatogue Street, whose early development dates to the late 17th century, with the oldest surviving buildings dating to 1730. Most of the properties in the district are Colonial, Federal, or Greek Revival in character, with only a few later Victorian houses. In the early 20th century Colonial Revival houses sympathetic to the earlier buildings.

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.

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 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.

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.

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.

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

Simsbury Center is a census-designated place (CDP) that consists of the central settlement, and the neighborhoods immediately surrounding it, in the town of Simsbury, Connecticut, in the United States. As of the 2010 census, the CDP had a population of 5,836. The core area of the CDP is listed as the Simsbury Center Historic District on the National Register of Historic Places.