Litchfield is a town in and former county seat of Litchfield County, Connecticut, United States. The population was 8,466 at the 2010 census. The boroughs of Bantam and Litchfield are located within the town. There are also three unincorporated villages: East Litchfield, Milton, and Northfield. Northfield, located in the southeastern corner of Litchfield, is home to a high percentage of the Litchfield population.

Great Barrington is a town in Berkshire County, Massachusetts, United States. It is part of the Pittsfield, Massachusetts, Metropolitan Statistical Area. The population was 7,104 at the 2010 census. Both a summer resort and home to Ski Butternut, a ski resort, Great Barrington includes the villages of Van Deusenville and Housatonic.

The Hudson Valley (also known as the Hudson River Valley) comprises the valley of the Hudson River and its adjacent communities in the U.S. state of New York. The region stretches from the Capital District including Albany and Troy south to Yonkers in Westchester County, bordering New York City.

The Berkshires (locally ) are a highland geologic region located in the western parts of Massachusetts and northwest Connecticut. The term "Berkshires" is normally used by locals in reference to the portion of the Vermont-based Green Mountains that extend south into western Massachusetts; the portion extending further south into northwestern Connecticut is grouped with the Connecticut portion of the Taconic Mountains and referred to as either the Northwest Hills or Litchfield Hills.Also referred to as the Berkshire Hills, Berkshire Mountains, and Berkshire Plateau, the region enjoys a vibrant tourism industry based on music, arts, and recreation. Geologically, the mountains are a range of the Appalachian Mountains. The Berkshires were named among the 12 Last Great Places by The Nature Conservancy.