2026 Compare Cities Rankings:
Winter Haven, FL vs Pittsfield, MA

#25 Drought-Riskiest Cities

#81 America's Best and Worst Cities for Crime (Mid-Size Metro Areas)

#84 America's Migraine Hot Spots

#98 Most Comfortable Summer Cities

#126 2005 Best Places to Live

#337 Best Green Cities

#4 America's Best and Worst Cities for Crime (Smallest Metro Areas)

#14 Best Green Cities

#14 Most Competitive Private Colleges

#81 America's Most (and Least) Stressful Cities (117 Smallest Metro Areas)

#243 2005 Best Places to Live

I moved here 4 years ago from Sarasota FL., because it seemed quiet, calmer, less expensive, and a reasonable distance back to SRQ, Tampa, and Orlando. What a mistake!  More

Definitely NOT a fan. My son moved me here without checking the rental home or neighborhood. WOW, we're we in for a surprise. It's total ghetto. I would NEVER  More

I lived in Bartow, right down the road from WH for many years. This is not a metropolitan area. It is middle class, bedroom community. It will take you less than an hour  More

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

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

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