Florida is a town in Berkshire County, Massachusetts, United States. It is part of the Pittsfield, Massachusetts Metropolitan Statistical Area. It is home to the east portal of the Hoosac Tunnel, as well as Whitcomb Summit, the highest point of the Mohawk Trail. Florida contains the village of Drury. At the 2020 census the town had a total population of 694. …Florida is a town in Berkshire County, Massachusetts, United States. It is part of the Pittsfield, Massachusetts Metropolitan Statistical Area. It is home to the east portal of the Hoosac Tunnel, as well as Whitcomb Summit, the highest point of the Mohawk Trail. Florida contains the village of Drury. At the 2020 census the town had a total population of 694. Despite the town’s name, Florida is statistically the coldest and snowiest town in Massachusetts.