Pittsfield is the county seat and the largest city in Berkshire County, Massachusetts. It is a very safe and peaceful community, very popular among single retired people. It is worth mentioning that it ranked among the Top 10 US cities for single retired people (US News, 2012). Overall, Pittsfield is Berkshire’s cultural and recreational hub. This is where the Boston Symphony Orchestra is being housed during the summer months. Other cultural points of interest include the majestic and fully renovated Colonial Theater (Hillary Clinton named this beautiful theater built in 1903 as a National Historic Treasure), the Berkshire Museum, the multiplex Beacon Cinema, and the Barrington Stage Company. Another great Pittsfield cultural and historic gem is the Arrowhead, Herman Melville’s home. Herman Melville was the author of the best-seller book “Moby Dick.” For the outdoors enthusiasts, we suggest you explore the 11,000-acre Pittsfield State Forest; an ideal place for hiking, biking, picnicking, swimming, and skiing. Regarding budget accommodation, there are more than 60 and nearby Pittsfield and the cost per room per night mostly varies between $50 – $200.