This town of 18,600 overlooking Long Island Sound is so New England picturesque that former president Bill Clinton singled it out in his memoir, My Life, as an "especially old and beautiful" favorite during his time at Yale. But at a mere 36 square miles along the Connecticut shoreline, Madison is easy to miss—and residents happen to like it that way.
Almost exactly halfway between New York City and Boston, Madison attracts a sophisticated mix of professionals—lawyers, accountants, architects—as well as a growing community of artists. They frequent the town's independent boutiques and family-owned restaurants, most of which are housed in the two-story shingled and redbrick buildings (many dating from the 1930s) that line Main Street. In the summer, a scenic green in the heart of downtown hosts outdoor concerts and a farmers' market.
Left: R.J. Julia Booksellers, a Publisher's Weekly Bookseller of the Year and the crown jewel of downtown