Pittsfield is the largest city in the Berkshires and the county seat of Berkshire County. If you are visiting or driving through you might visit:
Dottie’s Coffee Lounge: At 444 North St., this is a fun spot for coffee and food in the heart of downtown Pittsfield.
Berkshire Museum: The museum was founded in 1903 by Zenas Crane. The Crane Family were the owners of Crane & Company which is known for its paper and stationery products. Crane purchased many of the Museum’s first acquisitions including a large group of paintings from the Hudson River School which included works by Frederic Church, Albert Bierstadt, Thomas Cole, Thomas Hill, George Inness, Thomas Moran and Aaron Draper Shattuck. They also have works by Calder. They also feature temporary exhibitions. 39 South St.
Local friends recommend the Berkshire Theatre Group for its good performances. You can choose from performances in Stockbridge at The Berkshire Theater Festival Campus or in the Pittsfield Colonial Theatre/Garage.
There is also the Barrington Stage Company for theater in downtown Pittsfield. They offer performances from May to October in three downtown locations.
For those interested in design and history, you might enjoy the Hancock Shaker Village where you can visit the museum featuring their furniture, textiles, tools and more.
If you want to stay in the area, then you might consider the boutique Hotel on North with its eclectic style. It has been receiving great recent press. 297 North St.