Ice Glen

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.

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 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.

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 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.

The National Shrine of The Divine Mercy is a Catholic shrine located in Stockbridge, Massachusetts. The priests and brothers of the Congregation of Marian Fathers of the Conception of the Most Blessed Virgin Mary have resided on Eden Hill in Stockbridge, since June 1944. Father Walter Pelczynski, MIC, with the assistance of local clergy and friends of the Marian community, initially purchased 50 of the 370 acres (1.5 km2) that constituted the "Eden Hill" estate in November, 1943. The house was to serve as the novitiate for a newly formed province. An image of "The Divine Mercy" was enshrined in one of the small chapels where the members of the community prayed daily a perpetual novena to the Divine Mercy. Pilgrims began to arrive the very next spring to celebrate the Feast of The Divine Mercy (the Sunday after Easter). By the end of World War II in 1945, pilgrims in growing numbers came to offer thanksgiving for graces received through the Divine Mercy message and devotion. They urged the Marians to build a shrine to Jesus, The Divine Mercy, as a votive of thanks. The Fathers decided to accede to the requests since there was also a need for a larger chapel to accommodate a growing community. The construction of the present Shrine began in 1950 and was completed and solemnly dedicated by Springfield Bishop Christopher Weldon in 1960. In 1996, the United States Conference of Catholic Bishops declared it a National Shrine in accord with Church law. The National Shrine has drawn thousands of pilgrims from around the world.

The "Sedgwick Pie" is a cemetery plot in the United States. It is the family burial plot of the Sedgwick family in Stockbridge Cemetery, Stockbridge, Massachusetts, and gets its nickname from its shape and layout.

The Main Street Historic District is a historic district encompassing the scenic and historic portions of Main Street in Stockbridge, Massachusetts. The downtown portion of Main Street is widely recognizable due to its use by Norman Rockwell in his 1967 painting, Main Street, Stockbridge at Christmas. The central portion of Main Street is a broad street with wide green lawns, anchored by a traditional New England town center containing a church and municipal buildings. Along this part of Main Street is the Mission House, a National Historic Landmark that is one of oldest buildings in Stockbridge, dating to the early 1740s. Further to the west the road is more rural, and the district's western boundary is at the crossing of Main Street over the Housatonic River. The eastern part of the district includes the retail heart of the town, including the Red Lion Inn and several blocks of shops. The far eastern part of the district is Laurel Hill, a wooded park with views of the town center. The district was added to the National Register of Historic Places in 2002.The Stockbridge area has a significant prehistory of Native American use, with archaeological evidence of human use on at least a seasonal basis dating back for centuries. In the early 18th century it was settled by Mahican Indians who had been driven from the Hudson River area by conflict with the Mohawks. These uses included the establishment of a Native burying ground, which is within the bounds of this district. In 1734, the Province of Massachusetts Bay founded a "Praying Indian" community, with its main settlement where the downtown area is now. The arrival of English squatters and conflicts over land usage patterns led to the Natives eventually losing control of the community. The area's colonial settlement accelerated after the end of the French and Indian War in 1763. The Red Lion Inn opened in 1775, and it flourished in the early 19th century as a crossroads community not far from the county seat at Lenox.

Naumkeag is the former country estate of noted New York City lawyer Joseph Hodges Choate and Caroline Dutcher Sterling Choate, located at 5 Prospect Hill Road, Stockbridge, Massachusetts. The estate's centerpiece is a 44-room, Shingle Style country house designed principally by Stanford White of McKim, Mead & White, and constructed in 1885 and 1886. The estate is noted for its large gardens, which were designed in the mid-20th century by noted landscape designer Fletcher Steele in conjunction with Mabel Choate. A National Historic Landmark District, Naumkeag is now owned by The Trustees of Reservations, who operate it as a nonprofit museum.