Watch Hill, Rhode Island
Unless you own a home in Watch Hill, you’ve probably never even heard of this affluent coastal enclave. Here’s what you’re missing: a walkable village with cedar-shingled cottages, waterfront mansions (ahem, Taylor Swift), blue hydrangeas, beautiful beaches, an ice cream shop, and an old-timey carousel. If you want to stay the night, can book a room at the Ocean House, an enduring grande dame hotel, or the recently revamped Watch Hill Inn. Don’t miss these other romantic small town destinations across the country.
Madison proves that good things come in small packages. It may measure just 37 square miles and have a population of 18,200 residents, but this Connecticut shoreline community delivers a major dose of quintessential New England charm. In fact, Madison made such an impression on Bill Clinton during his time at Yale that he mentioned it in his memoir, My Life, calling it “especially old and beautiful.”