Make a reservation for dinner at Persimmon, an intimate 38-seat bistro with the most sophisticated menu in town. Chef Champe Speidel, a three-time James Beard Award semifinalist, cooks modern American dishes that push boundaries without testing your patience, like mussels served on edible “shells” made from potatoes and squid ink. Order the five-course tasting menu ($65, additional $38 for wine pairings), which changes daily and is interspersed with additional one-bite treats that you won’t find on the menu.
Walk along the harbor after dinner at Hourglass Brasserie (reservations recommended), which serves French cuisine with contemporary flourishes in a converted garage. The chef has an eye for stunning presentations and unique ingredient combinations, evident in a spring-vegetable salad ($10) with smoked goat cheese, pumpernickel “soil,” sorrel, and pea tendrils; and halibut in a Madras curry with turnips ($28).
Dine al fresco at DeWolf Tavern, a casual waterfront restaurant in a renovated warehouse dating back to 1818. Chef Sai Viswanath’s Indian-inflected menu features meats roasted in a traditional tandoor oven, excellent sandwiches made with naan (from $12), and chickpea-battered shrimp with a sweet chili sauce ($10). The bar holds a wide selection of rums, in a nod to the town’s history as a trading port.