America's Greatest Main Streets
Danita Delimont / Alamy
Although Nantucket—all 105 square miles of it—is a designated National Historic District, its cobblestoned Main Street is the island’s historic heart. Lined with grand Greek Revival buildings, elm trees, and countless benches, the street’s mix of chic boutiques and old-fashioned storefronts (selling needlepoint belts, saltwater taffy, and anchor-shaped door knockers) leads right down to the busy harbor, once the world’s whaling capital. The best people-watching is in summer, when the population mushrooms from 10,000 to 50,000, and Main Street throngs with strolling, gallery-poking visitors.
Worth a Stop: Nantucket Pharmacy, at 45 Main, scoops cones and pulls old-fashioned milkshakes from behind its soda counter.