Settled in 1660, Westchester’s smallest city has always provided a nautical nest for the maritime-inclined. Gracing the deep blue shores of the Long Island Sound, this once-upon-a-time oystering community has unfurled into a sophisticated albeit leisurely suburb, a picturesque contrast from New York’s concrete bones that’s just a train ride away. Along the harbor, and over by the beach, a spectrum of slope-roofed cottages, columned Colonials and modern stone manors stake their claims amongst forsythia, hydrangeas and cherry blossoms. Rye Playland, with its trestle-y Dragon Coaster and art deco flourishes, is the nation's only county-run amusement park and a beloved relic of old-fashioned seaside fun. Distant sailboats dot the sound in summertime, and in town you’ll find redbrick store fronts filled with all the treasures to top off a linen-lined picnic basket. A serene wildlife sanctuary on the water provides serenity for visitors and ducks, shaded at sunset with blazing pink hues.