2026 Compare Cities Rankings:
Jackson, MI vs Winter Haven, FL

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

#19 America's Migraine Hot Spots

#245 2005 Best Places to Live

#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

I lived in Jackson for a long time I lived on 1st and 3rd Street right over by Frank's party store before that b**** burnt down. My dad and I would sit out on the front  More

I spent 20 years of my life fighting for freedom only to buy a second home in Jackson, biggest mistake of my life, and have the rights I fought for take away by a  More

Never never ever move to this town! I was born there, grew up around there, made the tragic mistake of moving back there once and will never ever set foot there again!  More

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