2026 Compare Cities Rankings:
Winchester, VA vs Sheboygan, WI

#17 Emerging Metropolitan Areas

#231 Best Green Cities

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

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

#199 2005 Best Places to Live

#210 Best Green Cities

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

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

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

my wife and I moved to Sheboygan from McHenry County, Illinois. We are origional from rural from Wisconsin. Sheboygan has more restaurants, arts, and recreation than  More

Sheboygan is located on Lake Michigan, which is a great feature. The lake is scenic, provides recreation, and moderates the climate by keeping it cooler in summer and  More

Sheboygan is located on Lake Michigan, which is a great feature. The lake is scenic, provides recreation, and moderates the climate by keeping it cooler in summer and  More