While you may not be familiar with Pittsfield, you’ve probably heard of The Berkshires and this enigmatic little city sits right in the heart of that famous region. It’s elevation provides expansive views of the Hoosac and Tactonic hills covered with eastern hardwood forests, six lakes, and the powerful Housatonic River.

Like many places in New England Pittsfield’s history is very long and very interesting and chock full of odd characters. The most famous of these is Herman Melville, who wrote Moby Dick at his Arrowhead home. The historic Colonial Revival home of another famous citizen, Thaddeus Clapp, has been restored as a gracious Pittsfield Massachusetts bed and breakfast.