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

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Highlights
Are people in Winchester older or younger than people in Pittsfield?
- The Median Age in Winchester is 8.0 years younger than in Pittsfield.

Are housing costs cheaper in Winchester or Pittsfield?
- Winchester housing costs are 26.2% more expensive than Pittsfield housing costs.

Which city has a longer commute, Winchester or Pittsfield?
- The average commute for residents of Winchester is 7.2 minutes longer than it is for residents of Pittsfield.

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.

Things to do in Winchester?
Winchester is located in the northern Shenandoah Valley of Virginia. It's a historically significant city known for its rich Civil War history and architectural attractions like Winchester National Cemetery, as well as its numerous outdoor activities like hiking, kayaking, and fishing. The city also boasts an array of art and cultural offerings, with events such as the annual Hillbilly Festival taking place throughout the year.

 Pittsfield, MAWinchester, VAUnited States
 Population  Unlock28,194329,725,481
 Median Income$59,522  Unlock$69,021
 Median Age  Unlock36.638.4
 Avg. Home Price$263,800  Unlock$338,100
 Unemployment Rate  Unlock4.6%6.0%
 Avg. Commute Time17.59  Unlock26.38
Reviews for Pittsfield    6 Reviews

Over 10 years ago

I have grown up in Pittsfield, moved away, and came back. The loss of the GE manufacturing plant in the 80's adversely affected this blue collar city. This is not the  More

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Pittsfield has done nothing to attract any form of business for the 40 of 47 years that I have lived here. The current tax rate is now 3.7% for business property - that  More

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Hello, I was surprised to see Pittsfield, MA, listed as one of the towns with least crime. We've had 4 shootings since the beginning of the year! Where do you get  More

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Reviews for Winchester    17 Reviews

I have lived in Winchester for 13 years and I find the locals to be rude, unpleasant and loud. Women worse than men... that's not to say all is bad, the city has some  More

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Over 9 years ago

Worst place I have ever lived. My neighbors hate jemmy since I am not a clone. They do not respect other people's property.I put up a fence and the same day the  More

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I would have to say I agree with much of what another individual wrote: it's like going back in time or living in a place that refuses to adapt to cultural diversity.   More

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