Samuel's Sweet Shop

Samuel's Sweet Shop has occupied a narrow corner of East Market Street since 1994, running on the reputation Ira Gutner built over two decades behind the counter. When Gutner died unexpectedly in 2014, the town worried it would close for good. Three Rhinebeck-connected actors who'd grown up on its candy (Paul Rudd, Jeffrey Dean Morgan, and Hilarie Burton) bought it instead and kept it running.

The case up front holds Rhinebeck's only real chocolate counter: hand-dipped truffles and dark chocolate bark studded with almonds, dried cherries, and grey sea salt. Vintage candies most of us haven't seen since childhood sit alongside: wax bottles, Mary Janes, ribbon candy, the stuff other stores stopped carrying decades ago. A Partners Coffee espresso bar runs the length of one wall, so you can pair your cappuccino with a truffle.

The staff know the shop's back catalog cold. They'll point you toward a candy you mentioned once in passing or suggest a chocolate to pair with your coffee order. It's a small space with narrow aisles, so expect a wait on Saturday afternoons, and know it's tight going for a wheelchair.