Beartown State Forest

The Upper Housatonic Valley National Heritage Area is a federally designated National Heritage Area in the U.S. states of Connecticut and Massachusetts. The heritage area interprets and promotes the historical, cultural and scenic features of the upper Housatonic River valley in the western part of both states. The heritage area focuses on five themes: the area's role as a resort for writers, artists, actors and musicians, the scenic landscape, the area's role in industry, the American Revolutionary War, and the social and religious groups associated with the area.The National Heritage Area comprises the towns of Colebrook, Norfolk, North Canaan, Canaan, Salisbury, Sharon, Cornwall, Warren and Kent in Connecticut, and New Marlborough, Sheffield, Mount Washington, Egremont, Alford, Great Barrington, Monterey, Tyringham, Becket, Washington, Lee, Stockbridge, West Stockbridge, Richmond, Lenox, Hancock, Pittsfield, Lanesborough, Dalton and Hinsdale in Massachusetts.

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 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 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.

The Tyringham Shaker Settlement Historic District was a historic Shaker village on Jerusalem Road in Tyringham, Massachusetts. Among the buildings in the village were mills and workshops. There was a reduction in members prior to the American Civil War and in the 1870s the remaining "believers" moved to Hancock Shaker Village in Massachusetts and Enfield Shakers Village in Connecticut. In 1874 the Shakers traded the property to a New York City doctor, Joseph Jones, for property in Pennsylvania. Dr. Jones open a summer retreat and boardinghouse called "Fernside". In 1889 the property was sold to the Tyringham Forest Club. It is now farmland. It was added to the National Register of Historic Places in 1987.

Eagleton School was a residential treatment facility located in Great Barrington, Massachusetts for boys ages 9–22 who have a variety of emotional and behavioral problems. It was privately owned by Bruce Bona. It was the host of the Great Barrington Christmas party.

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.

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 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 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.