Glendale, Massachusetts

Chesterwood was the summer estate and studio of American sculptor Daniel Chester French (1850–1931) located at 4 Williamsville Road in Stockbridge, Massachusetts. Most of French's originally 150-acre (61 ha) estate is now owned by the National Trust for Historic Preservation, which operates the property as a museum and sculpture garden. The property was designated a National Historic Landmark in 1965 in recognition of French's importance in American sculpture.

The Glendale Power House is a historic power station on the Housatonic River, just off Massachusetts Route 183 in Stockbridge, Massachusetts. The 1905 power house, built for the Monument Mills, was one of the first places in the United States where electricity was generated for the purpose of providing power to an industrial facility. The station was listed on the National Register of Historic Places in 1982. The facility has been rehabilitated and converted into modernized hydroelectric power generation plant.

The Norman Rockwell Museum is an art museum in Stockbridge, Massachusetts, United States, dedicated to the art of Norman Rockwell. It is home to the world's largest collection of original Rockwell art. The museum also hosts traveling exhibitions pertaining to American illustration.

The Berkshire Botanical Garden, is a 15-acre (6.1 ha) botanical garden in Stockbridge, Massachusetts, United States. Its collections contain over 3,000 species and varieties, with an emphasis on plants that thrive in the Berkshires. The Garden was founded in 1934 as the Berkshire Garden Center, and its public display gardens are among the oldest in the United States.

Berkshire Country Day (BCD) is an independent school for pre-schoolers through eighth grade. It is located at 55 Interlaken Road/Route 183 in Berkshire County, Massachusetts near the town of Lenox.

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.

Stockbridge is a town in Berkshire County in Western Massachusetts, United States. It is part of the Pittsfield, Massachusetts, Metropolitan Statistical Area. The population was 2,018 at the 2020 census. A year-round resort area, Stockbridge is home to the Norman Rockwell Museum, Naumkeag, a public garden and historic house, the Austen Riggs Center (a psychiatric treatment center), and Chesterwood, home and studio of sculptor Daniel Chester French.

Monument Mountain is a 2.5-mile (4.0 km) long quartzite ridgeline located in Great Barrington and Stockbridge, Massachusetts in the Berkshires geology. Beside the high point, 1,739 feet (530 m), the mountain has several distinct features, most notably the open, knife-edge Peeskawso Peak, 1,642 feet (500 m) located on the southeast side of the mountain within the 503-acre (204 ha) Monument Mountain reservation managed by The Trustees of Reservations. The mountain receives over 20,000 visitors per year. Devil's Pulpit, part of Peeskawso Peak, is a free-standing pillar of stone. Flag Rock, located on the southwest side of the mountain, is an open ledge overlooking the village of Housatonic. The only official trails on the mountain ascend Peeskawso Peak from a parking lot on Massachusetts Route 7 north of Great Barrington center. There is no fee for members of The Trustees and a parking fee of $5 for non-members. An unnamed waterfall is located to the northeast of Peeskawso Peak along the Hickey Trail. Views from Peeskawso Peak include the Housatonic River Valley, The Berkshires, the Taconic Mountains, and the Catskill Mountains of New York. The west side of Monument Mountain drains into the Housatonic River thence into Long Island Sound. The east side of Monument Mountain drains into Konkapot Brook thence into the Housatonic River.

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.

Oronoque was built as the country home of Birdseye Blakeman, Esq., and is located in Stockbridge, Massachusetts. The building was designed by William Henry Miller and built by Powers & Sons, Rochester. The house exterior was built to resemble a royal hunting lodge. The 12 acre grounds were landscaped by Nathan Franklin Barrett.

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.

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.