Bartholomew's Cobble

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.

Canaan is a village and census-designated place (CDP) within the town of North Canaan in Litchfield County, Connecticut, United States. Formerly known as Canaan Depot, the village is more commonly known as Canaan Village to distinguish it from the town of Canaan located to the south of North Canaan. The Canaan Village Historic District is listed on the National Register of Historic Places. As of the 2010 census, the CDP had a population of 1,212, out of a total population of 3,315 in the town of North Canaan. The historic district comprises about 93 acres (380,000 m2), covering the central business district and surrounding residences of the village that preserve the period from the mid-19th to early 20th centuries. Canaan village developed as a regional commercial center, first by the construction of the north-south Housatonic Railroad, and then by the arrival of the east-west Connecticut Western Railroad. This junction made the village a major transit point for bringing the area's commercial goods to market. The district includes the Canaan Union Depot, built in 1872 to serve the two railroads.The Canaan Fire Company was established in 1911.

The Canaan Union Depot, also known as the Union Depot, is located in Canaan Village, in the town of North Canaan, Connecticut, and is a former union station. It was built in 1872 at the junction of the Housatonic Railroad and the Connecticut Western Railroad which was acquired by the Central New England Railway.

The Isaac Lawrence House is a historic house on Elm Street in the Canaan Village of North Canaan, Connecticut. Built about 1751 by one of the town's first settlers, the house has served as a residence and tavern, serving customers on the adjacent travel route. The property is also of archaeological significance, with historical artifacts dating to the 18th century. It was listed on the National Register of Historic Places in 1983.

The General John and Mary Fellows Farmstead is a historic farm property at 1601 Barnum Road in Sheffield, Massachusetts. Its farmhouse, dating to the 1760s, was home to American Revolutionary War general John Fellows. The property was listed on the National Register of Historic Places in 2018.

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 Twin Lakes are adjacent Lakes Washining and Washinee, commonly referred to as East Twin Lake and West Twin Lake, in Salisbury amidst Connecticut's Northwest Hills.

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,

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.

The Scoville Powerhouse is a historic former power generation facility at Twin Lakes and Taconic Roads in the Taconic neighborhood of Salisbury, Connecticut. Built about 1899, it provided power to the surrounding estate of the Scoville family, owners of local iron mining and processing operations. It was converted into a privated residence in the 1950s, and was listed on the National Register of Historic Places in 1984 for its distinctive architecture.

Clayton, Massachusetts is the southernmost community in Berkshire County, Massachusetts. It is part of the town of New Marlborough.

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.