Hendrick Cottage

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 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.

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 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.

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.

Belden Forest is a 40-acre (16 ha) wooded area owned by the Town of Simsbury, which was inducted into the Old-Growth Forest Network in October 2019. The trails are open to the public.The property was previously part of the summer residence and estate of Amos R. Eno, and was acquired by the Town of Simsbury in 1946. The forest includes a large stand of old eastern white pines; many of which are over 100 feet tall. It also has beech trees, eastern hemlocks, oaks, maples and birch trees. All of the trees in the forest are permanently protected from commercial logging.

The Simsbury Townhouse is a historic municipal building at 695 Hopmeadow Street in Simsbury, Connecticut. Built in 1839, it was Simsbury's town hall until 1931, and is a good local example of Greek Revival architecture. It was listed on the National Register of Historic Places in 1993. It continues to serve as a community resource.

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.

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.