Pittsfield is Berkshire County’s largest city. The unique mix of urban, suburban, and rural atmospheres fosters a wide range of engaging activities for locals and tourists. Downtown Pittsfield is typically lively with restaurants, bars, galleries, a museum, and more. Scattered throughout the city, you’ll find a good assortment of historic and culture-rich places to experience. Outside of this, there’s a decent amount of wilderness for being such a populated city. Multiple lakes, forests, hills, and meadows give people places to hike, cycle, swim, kayak, canoe, and more. Bousquet Ski Area is in Pittsfield too—a great place for some family fun.
At large, the city has more of a dated feel as opposed to modern, which is in part due to the preservation and appreciation of the historic buildings around the area. When it comes to dining and shopping, local businesses are abundant and beloved throughout Pittsfield. Immersive community-wide events take place here and there, especially in the warmer seasons. It’s no Boston or NYC, but the Berkshire spin on this smaller-scale city makes it a special place to be.