2025 Compare Cities Overview:
Winchester, MA vs Pittsfield, MA

Are people in Pittsfield older or younger than people in Winchester?
- The Median Age in Pittsfield is 2.2 years older than in Winchester.

Are housing costs cheaper in Pittsfield or Winchester?
- Pittsfield housing costs are 78.7% less expensive than Winchester housing costs.

Which city has a longer commute, Pittsfield or Winchester?
- The average commute for residents of Pittsfield is 15.4 minutes shorter than it is for residents of Winchester.

Things to do in Winchester?
Winchester is a lovely suburban town located just 8 miles north of Boston in Middlesex County Massachusetts. Serving as home to some of New England’s oldest homes Winchester Center is a great place to explore history while also benefiting from access to Boston’s cultural assets. This well ranked school district also offers families plenty of educational opportunities as well.

Things to do in Pittsfield?
Pittsfield, Massachusetts lies within Berkshire County providing visitors great entertainment opportunities from the Colonial Theatre to Hancock Shaker Village along with food spots like Rubiner’s Cheese & Grocery Store.