2025 Compare Cities Rankings:
Pittsfield, MA vs Estero, FL

#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

#1 Most Popular Cities for the Holidays

#8 Best Cities for Teleworking - Small Metro Areas

#20 Drought-Riskiest Cities

#45 America's Migraine Hot Spots

#58 2005 High Gas Prices

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

#67 High Gas Prices - Which Cities are Hit the Hardest?

#97 Most Comfortable Summer Cities

#105 Best Green Cities

#220 2005 Best Places to Live

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

Estero, FL is wonderful in every way. It is an upscale village sitting between SW Florida International Airport in Fort Myers, FL, and the posh city of Naples, FL.  More

A slice of paradise exists here in southwest Florida! Winters are warm with average highs in the 70s along with abundant sunshine. Morning lows average in the 50s.   More