Upper Housatonic Valley National Heritage Area

The Ice Glen is a ravine in the southeast area of Stockbridge, Massachusetts. The park is essentially a lush, untended, romantic landscape consisting of piled rocks thick with mosses. Ice Glen derives its name from the fact that ice can persist at the bottom of deep rock crevices there into the summer. Its north-south orientation protects the glen from much direct sunlight. Surrounding the glen is an old growth forest, rare in New England.In 1891, the Ice Glen was donated by David Dudley Field to the Laurel Hill Association, the first incorporated village improvement society in the United States. As the association's existing property at Laurel Hill, which directly abuts the village center of Stockbridge, is separated from the forested hills in which the Ice Glen is located by the Housatonic River, the association built a bridge to connect the two properties. A trail still runs from Laurel Hill, behind the former Stockbridge Plain School, now the Town Offices building, over the bridge, through the glen, and exits on Ice Glen Road behind Villa Virginia. Beginning in the late nineteenth century, annual torchlight parades through the glen became popular.

Villa Virginia is a historic country estate in Stockbridge, Massachusetts on Ice Glen Road. Built in 1914–15, it is one of the last of the great Berkshire Cottages to be built in Stockbridge and a significant example of Mediterranean Renaissance Revival architecture. It was listed on the National Register of Historic Places in 1983.

Beartown State Forest is a publicly owned forest with recreational features located in the towns of Great Barrington, Monterey, Lee, and Tyringham, Massachusetts. The state forest's more than 10,000 acres (4,000 ha) include 198 acres (80 ha) of recreational parkland. It is managed by the Massachusetts Department of Conservation and Recreation.

The Merrell Tavern, known more recently as the Merrell Inn, is a historic tavern at 1565 Pleasant Street (Massachusetts Route 102) in South Lee, Massachusetts. Built in 1794 as a residence, it has served for most of two centuries as a local traveler's accommodation, and retains fine Federal period architectural details. > It was added to the National Register of Historic Places in 1972. It continues to serve its historic function, and is now operated as a bed and breakfast inn.

The Elm–Maple–South Streets Historic District is a historic district encompassing part of the historic downtown of Stockbridge, Massachusetts. The most prominent parts of Stockbridge lie within the Main Street Historic District, which abuts this district to the north. The southern boundary of this district is the railroad tracks that run parallel to the Housatonic River. The eastern boundary of the district is Laurel Hill, a wooded park overlooking the town, and the western boundary is a terraced shelf in the plains of the river. The district includes properties on Depot, Elm, Maple, and South Streets, and Laurel Lane. Unlike Main Street, this district consists of more densely place residences, and narrower roads containing businesses just off Main Street. Its buildings were mostly constructed during the late 19th and early 20th centuries, and partially reflect Elm Street's function as an industrial part of the town. The district was added to the National Register of Historic Places in 2004.Stockbridge was founded in the 1730s as a "Praying Indian" community, with its main settlement where the downtown area is now. South Street began as a Native American trail leading to the south, crossing the river at a fordable location. A bridge was first built near where the modern bridge now stands in 1744. The junction of Main and South Streets became a major local commercial nexus by later in the 18th century, with the area closer to the river where small industries began to flourish. One of Berkshire County's first printing operations was begun in this area, and there was by the mid-19th century a blacksmithy. A few houses stood in the area by the turn of the 19th century, but it was not until the 1850s that a significant number of houses began to be built south of Main Street. Many of these were populated by people engaged in trades for travelers, or otherwise engaged in business on Main Street. One of the older houses and the largest in the district, the Tidmarsh-Edwards House at 8 South Street, has had a number of notable residents, including politician and businessman John Z. Goodrich.

The Stockbridge Casino is a historic building at the junction of East Main Street and Yale Hill Road in Stockbridge, Massachusetts. Built in 1887, it is a prominent local work of architect Stanford White, and has served as a cultural center in the community since its construction, despite being moved in 1928. Now a part of the grounds of the Berkshire Theatre Festival, the building was added to the National Register of Historic Places in 1976.

Williams High School was a public high school located in the town of Stockbridge in the Berkshire Hills of western Massachusetts. Its history evolved from the town's earliest schools founded before and shortly after the American Revolutionary War. Students from Stockbridge, its small villages of Interlaken, Glendale and Larrywaug, and from the nearby town of West Stockbridge attended Williams High School. In April 1968 the school closed, when its students transferred to a new regional high school located in the town of Great Barrington.

The Red Lion Inn in Stockbridge, Massachusetts is one of the Historic Hotels of America of the National Trust for Historic Preservation. The main building of the inn offers 82 guest rooms. In addition to the inn itself, the hotel operates nearby guest houses and other properties as alternative lodging options.

Merwin House, also known as Tranquility, is a house located at 14 Main Street, Stockbridge, Massachusetts, USA. It is now a non-profit museum operated by Historic New England and sometimes open to the public. An admission fee is charged. The original brick, Federal-style house was constructed c. 1825 by the Dresser family, who sold it to William and Elizabeth Doane of New York City as a summer home in 1875. They doubled its size by adding a shingle-style ell, and also remodeled its interior. It was donated to the public by the Doanes' daughter, Vipont Merwin, who was born in the house in 1878 and died there in 1965. The property was acquired by Historic New England in 1966, whereupon it became a museum.The house currently reflects furnishings and a lifestyle of the late 19th century, with period antiques and items collected during world travel.

The Austen Riggs Center is a psychiatric treatment facility in Stockbridge, Massachusetts. It was founded by Austen Fox Riggs in 1913 as the Stockbridge Institute for the Study and Treatment of Psychoneuroses before being renamed in honor of Austen Riggs on July 21, 1919.

The South Lee Historic District encompasses the historic portion of the village of South Lee in Lee, Massachusetts. Extending mainly along Massachusetts Route 102 (Pleasant Street) between Fairview Street and the Stockbridge town line, the village is a well-preserved 19th-century mill village, with fine Federal and Greek Revival buildings and a later 19th-century paper mill. It was listed on the National Register of Historic Places in 1999.

The Mission House is an historic house located at 19 Main Street, Stockbridge, Massachusetts. It was built between 1741 and 1742 by a Christian missionary to the local Mahicans. It is a National Historic Landmark, designated in 1968 as a rare surviving example of a colonial mission house. It is now owned and operated as a nonprofit museum by the Trustees of Reservations.The town of Stockbridge was established in the late 1730s as a mission community to the Mahicans. John Sergeant was the first missionary, formally beginning his service in 1735. His first house, built in the valley where the Indians lived, has not survived; this house was built in the white community on the hill above the town following his marriage in 1739. It remained in the Sergeant family until the 1870s, and survived Gilded Age developments of the late 19th century. In the 1920s the house was purchased by Mabel Choate, owner of the nearby Naumkeag estate, and moved down into the valley. She and landscape designer Fletcher Steele restored the building, furnished it with 18th century pieces, and designed gardens to Steele's vision of what a colonial landscape might have been. Choate opened the house as a museum in 1930, and donated it (and eventually Naumkeag as well) to the Trustees of Reservations, who operate both properties as museums.