Named after a line from Hemingway’s The Sun Also Rises, {pretty to think so} occupies Rhinebeck’s historic Starr Institute library, where books once lined the shelves and now set the scene for dinner. The farm-to-table menu follows the Hudson Valley seasons, with dishes ranging from caviar-topped frites and oysters to crispy duck confit and market vegetables

A classic roadside stop, Del’s serves up juicy burgers, golden fries and small-batch ice cream made with milk from its own dairy farm in nearby Red Hook. The menu also features boozy milkshakes, from coffee and Irish whiskey to lavender-honey blueberry with gin. 

With its five-storey circular tower, wraparound veranda and wonderfully over-the-top Queen Anne architecture, Wilderstein looks ready for a period drama. The Rhinebeck estate was home to Margaret “Daisy” Suckley, a close confidante of Franklin D. Roosevelt, and its rooms still brim with family heirlooms and Victorian curiosities. Outside, three miles of woodland trails, rustic gazebos and Hudson River views make for a rather lovely detour.

Set in a beautifully curved brick building in Kingston’s historic Rondout neighbourhood, Rosie gives the old-school American general store a modern-day makeover. Shelves brim with freshly baked sourdough, baguettes, pastries and pantry staples, while the kitchen turns out breakfast sandwiches, mortadella heroes with pistachio and hot honey, and thick-cut pastrami on rye.