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Pittsfield, MA Vacation Packages

Pittsfield is the county seat of Berkshire County, Massachusetts, and is the largest city in The Berkshires region. Pittsfield’s downtown, known as the Upstreet Cultural District, boasts a lively roster of music, dance, theater, community festivals, and celebrations. It is one of the older cities in western Massachusetts and some of the oldest buildings in the region are located in Pittsfield, with a handful dating from the Colonial era.


Pittsfield, MA

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