The Town of Cheshire has been ranked 73rd among the Top 100 Places to Live in the U.S. (population 50,000 or less) by Money Magazine. Factors such as fiscal strenght and the economic environment, quality of life, education, and leisure and culture were analyzed. The magazine describes Cheshire as a "charming, garden-filled town," citing proximity to cities, good schools, a triple-A credit rating and the Rails to Trails program as benefits. Only four other Connecticut towns made this list, which is published every two years by the magazine. Cheshire was listed in the 2009 ranking as well.