Olean, NY, United States

With a population of just 13,937, Olean is hardly the bustling metropolis it once was. The glory days of oil and timber have given way to a persistent bureaucratic headache and a chilly climate more akin to the Allegheny Mountains than the rest of western New York. Still, the city remains the largest in Cattaraugus County, serving as a regional hub for business, transportation, and entertainment. For those drawn to small-town life and the occasional brush with Prohibition-era gangsters, Olean may be worth a look - but the winters are long, and the red tape is unforgiving.