Old Covered Bridge

The Sheffield Plain Historic District encompasses the original 18th-century village center of Sheffield, Massachusetts, United States. The linear district extends southward about 0.5 miles (0.80 km) from the junction of United States Route 7 and Cook Road, where the original town common is located. The district was primarily developed in the mid-18th and early 19th centuries. It was listed on the National Register of Historic Places in 1988.

Schenob Brook is a stream in Berkshire County, Massachusetts and Litchfield County, Connecticut, in the United States. Variant names are Kisnop Brook, Schenop Brook, and Skerrob Brook.Schenob Brook flows generally northward from Washinee Lake in Salisbury, CT, and merges with Hubbard Brook in Sheffield, MA which then flows into the Housatonic River a quarter mile downstream. The stream was named for John Sconnoup, an early settler of Dutch descent.

Sheffield is a town in Berkshire County, Massachusetts, United States. It is part of the Pittsfield, Massachusetts, Metropolitan Statistical Area. The population was 3,327 at the 2020 census. Sheffield is home to Berkshire School, a private preparatory school. The former resort town includes the village of Ashley Falls, and is bordered by various other towns and villages, such as Egremont and Great Barrington. Its southern border is the Massachusetts-Connecticut state line,

The Sheffield Center Historic District encompasses the historic village center of Sheffield, Massachusetts. The village extends linearly along United States Route 7, roughly between Maple Avenue and Berkshire School Road, and includes the town's major civic and religious buildings. The area's principal period of development was between 1760 and the 1890s. It was listed on the National Register of Historic Places in 1989.

The Wheeler Family Farmstead is a historic farm complex at 817 South Main Street in Great Barrington, Massachusetts. The farmhouse has elements dating to the 1730s, including evidence of building methods used by Dutch settlers of the Hudson River valley, and has been successively modified in each of the following centuries, with the last significant work occurring in the 1920s. All of the surviving farm buildings in the complex are at least 90 years old, and some date to the 19th century. The property was listed on the National Register of Historic Places in 2011, and is now the museum and headquarters of the Great Barrington Historical Society.

Berkshire School is a private, co-ed boarding school for grades 9 through 12 located in Sheffield, Massachusetts, USA.

The Colonel John Ashley House is a historic house museum at 117 Cooper Hill Road in Sheffield, Massachusetts. Built in 1735 by a prominent local leader, it is one of the oldest houses in southern Berkshire County. The museum is owned and operated by The Trustees of Reservations, and is listed on the National Register of Historic Places.

The South Egremont Village Historic District encompasses most of the village of South Egremont, Massachusetts, a well-preserved village whose architecture has seen relatively little alteration since the 1840s. It is located along Massachusetts Route 23 in the plains east of the Taconic Mountains. The district was listed on the National Register of Historic Places in 1984.

Ski Butternut, also known as Butternut Basin, is a ski resort in Great Barrington, Massachusetts, located on Warner Mountain in The Berkshires. Channing and Jane Murdock took control of the area in 1963, naming the area Butternut Basin after the large groves of butternut trees located in the basin of the mountain. Family friends of the Murdocks', the Kennedys visited Butternut.The mountain currently features 22 trails, ten ski lifts, two terrain parks, a tubing area, and a PSIA-affiliated ski school. Ski Butternut now features 3 quad lifts. In the off-season, the mountain hosts a number of summer concerts and festivals, including the annual Berkshires Arts Festival. The hours are Monday - Friday 9 AM - 4 PM, and 8:15 AM - 4 PM Saturdays, Sundays, and Holidays. Ski Butternut also offers tubing in the winter.

The Westover–Bacon–Potts Farm is a historic farm along Massachusetts Route 41 in Egremont, Massachusetts. Built beginning in 1744 on 150 acres (61 ha) of land, it is one of the best-preserved farmsteads of the period in Berkshire County. It was listed on the National Register of Historic Places in 1990. Until 2019, the property was owned by the Appalachian Trail Conservancy and was named the Kellogg Conservation Center. In 2019, Greenagers acquired the property "for a nominal sum" and renamed it the April Hill Conservation & Education Center.

Bartholomew's Cobble is a 329-acre (1.33 km2) National Natural Landmark, open space preserve, agricultural preserve, and bio-reserve located in southwest Massachusetts in the village of Ashley Falls abutting Canaan, Connecticut. The preserve contains more than 800 plant species, including North America's greatest diversity of ferns and the greatest overall biodiversity in Berkshire County, Massachusetts; it also contains Massachusetts' highest populations of ground nesting bobolinks. It was declared a National Natural Landmark in October 1971.The preserve includes two rocky knolls for which the property is named (the Cobbles), as well as floodplain along the Konkapot and Housatonic Rivers, working hayfields and pastures, meadows, and 1,000-foot (300 m) Hurlburt's Hill, an open hilltop with a panoramic view of The Berkshires, the Taconic Mountains, and the Housatonic River Valley. The property has been owned and managed by the non-profit conservation organization The Trustees of Reservations since 1946. Hiking trails and an interpretive center and museum are located on the preserve. Rangers and staff lead guided canoe trips on the Housatonic River in season.

The W.E.B. Du Bois Boyhood Homesite (or W.E.B. Du Bois Homesite) is a National Historic Landmark in Great Barrington, Massachusetts, commemorating an important location in the life of African American intellectual and civil rights activist W.E.B. Du Bois (1868–1963). The site contains foundational remnants of the home of Du Bois' grandfather, where Du Bois lived for the first five years of his life. Du Bois was given the house in 1928, and planned to renovate it, but was unable to do so. He sold it in 1954 and the house was torn down later that decade. The site is located on South Egremont Road (state routes 23 and 41), west of the junction with Route 71. Plans to develop the site as a memorial to Du Bois in the late 1960s were delayed due to local opposition. The site's proponents attributed this in part to racism, but opposition opinions were generally expressed in terms of rejecting Du Bois' more radical politics in later life. He left the US for Ghana in 1961 and did not return. On May 11, 1976, the site was declared a National Historic Landmark and listed on the National Register of Historic Places. The site was donated to the state in 1987, and is administered by the University of Massachusetts, Amherst.