Pittsfield is a small rural town located on Route 100 between Stockbridge and Killington, 20 miles from Rutland, and 13 miles from Killington Ski Area.  The center of town consists of a town green complete with a bandstand. 

Three country stores, a pizza shop, and a restaurant cater to the local trade as well as vacation travelers.  For places to stay, you can check out Casa Bella Inn, Swiss Farm Inn, or Clear River Inn & Tavern.  Another long-time Pittsfiled business resident is Colton Enterprises, Inc.  They provide kiln-dried firewood to homes and businesses throughout New England.  The unique Original General Store also makes its home in Pittsfield.  Another special attraction this town has to offer is the Tweed Valley Farm on Lower Michigan Road with their Gourmet Shiitake and Oyster Mushrooms grown in barn greenhouses along with an array of agricultural products. The orginal Hawk Mountain Vacation Homes are tucked in among the hills bringing a diversity of residents to this friendly community.  Fairly new to the area is The Amee Farm, which offers deluxe accommodations for a variety of events.

Pittsfield does not have a school. Students are tuitioned to schools in nearby Killington, Stockbridge, Bethel, Rochester and Woodstock.