Smithtown, NY, United States

With a population of 116,296, Smithtown may seem like a sleepy suburb, but the town's long history and Republican political dominance have created a persistent bureaucratic headache for residents. The founding legend of a bull-riding land grab may be apocryphal, but the town's origins dating back to 1665 lend an air of tradition - and inertia. While Smithtown has affluent enclaves, its diversity is limited, with the town skewing 95.51% white. For those seeking a well-off, politically conservative enclave on Long Island, Smithtown could be a good fit, but anyone looking for a dynamic, progressive community should look elsewhere.