County Living Magazine has named Rhinebeck one of the top 18 Most Charming Small Towns in America. In addition to being the home to America’s oldest operating inn and the Dutchess County Fairgrounds (which hosts the annual Dutchess Fair, the Country Living Fair and the Sheep and Wool Festival), Rhinebeck is home to an array of great dining options and shopping. Terrapin Restaurant has been voted the Best Restaurant in Dutchess County multiple years running.