Shepaug Valley School

Institute For American Indian Studies (IAIS) is a museum and research center in Washington, Connecticut. It is dedicated to preserving and sharing the culture and history of Native American peoples, particularly those from the Northeastern Woodlands. Exhibits include a replica Algonkian village, and nature trails and a garden with plants used by native peoples. The museum opened on July 1, 1975, as the American Indian Archaeological Institute and changed to the present name in 1991.

Judea Cemetery, also known as Old Judea Cemetery, is a colonial era burying ground located on Judea Road in Washington, Connecticut, United States. Before it became a separate town in 1779, and chose to name itself "Washington", the area was known as "Judea", and was part of Woodbury, Connecticut. Judea Cemetery is the site of a monument in honor of "Jeff Liberty and His Colored Patriots", erected in the early 20th century. The cemetery is thought to be the resting place of a number of African-American soldiers who served in the American Revolutionary War, including Jeff Liberty. Liberty was owned by Continental Army Captain Jonathan Farrand, who is buried in Old Judea. Captain Farrand manumitted Jeff Liberty for fighting in the Continental Army. "Liberty" is known to have been chosen as a surname by a number of enslaved people who were manumitted in this era.Spy thriller novelist Edward S. Aarons (1916–1975) is buried in Judea.

The Washington Green Historic District encompasses the historic village green of the town of Washington, Connecticut, and much of the surrounding village center. It extends mainly along Kirby and Woodbury Roads, and includes a diverse collection of architecture from the 18th to early 20th centuries. It was listed on the National Register of Historic Places in 1995.

The Frederick Gunn School is a private, coeducational, boarding and day prep school for students in grades 9–12 and postgraduate, located in rural Connecticut, United States. The 220-acre (0.89 km2) campus borders the village green of Washington, a small, historic town in Litchfield Hills. Formerly known as The Gunnery and Mr. Gunn's School, it was named for its founder, has no military affiliations and is a non-sectarian school. The Frederick Gunn School was founded in 1850 by Frederick W. Gunn, a teacher, abolitionist, and father of recreational camping in America, based on his belief that strength of character was the goal of education.

Roxbury Center is the central village of Roxbury, Connecticut. Centered at the junction of Connecticut Routes 67 and 317, it has been the center of town civic life since the mid-18th century. The village was listed on the National Register of Historic Places in 1983.

Roxbury is a town in Litchfield County, Connecticut, United States. The population was 2,260 at the 2020 census. The town is located 65 miles (105 km) northeast of New York City, and is part of the Northwest Hills Planning Region.

Mine Hills Preserve is a natural and historical conservation area on Mine Hills Road in northwestern Roxbury, Connecticut. Owned by the Roxbury Land Trust, it protects the site of a well-preserved 19th-century iron mine and furnace works. Several miles of trails provide access to abandoned quarry areas and the preserved remains of the iron works, whose uses are explained by informational panels. The preserve is open from dawn to dusk. The 360-acre (150 ha) preserve was listed on the National Register of Historic Places in 1979.

Woodbury Ski Area was a ski area located in Woodbury, Connecticut. This small ski area was in northwestern Connecticut, about 2 hours from New York City. The skiing and snow tubing operations were serviced by a chairlift and multiple surface lifts. Local residents referred to it as "Rod's" after its owner, Olympic skier Rod Taylor.Taylor opened the resort in 1972. Taylor took pride in Woodbury being the first ski area in Connecticut to open each season.The ski area closed in 2016 following a drought and has not reopened. It has since been bought, however, its future is uncertain. The ski area may reopen in the coming years, as work has begun to get the park operational again.

The Sunny Ridge Historic District encompasses a historic former crossroads village in Washington, Connecticut. It consists of properties abutting the triangular intersection of Sunny Ridge Road, Nettletown Hollow Road, and Old Litchfield Road (Connecticut Route 109). This area was in the 18th and 19th centuries a stop on a north-south stagecoach and mail route. It was listed on the National Register of Historic Places in 1995.

The Calhoun–Ives Historic District, or more formally the Calhoun Street–Ives Road Historic District, is a locally and nationally designated rural agricultural historic district in the town of Washington, Connecticut. It is located a mile north of the village of Washington Depot, Connecticut. It runs along Calhoun Street and Ives Road. It is characterized by modestly scaled 18th and 19th century farmhouses, together with accompanying agricultural outbuildings, farm fields, and fruit orchards, set along roads lined by stone walls. The district was listed on the National Register of Historic Places in 1995.