With teal-blue leather couches ready to sink into, squiggly mirrors and a skylight overhead, Eliza Bistro brings a little design flair to Kingston’s dining scene. The menu mixes neighbourhood-bistro comfort with Italian-inspired plates, including cavatelli tossed with honeynut squash, arugula and confit maitake mushrooms. 

With a wood-fired oven turning out inventive pies alongside house-made pasta and seasonal sides, LOLA has seriously raised the bar for Kingston's pizza night. The Tiger Paw, topped with pepperoni and a drizzle of chilli honey, brings a sweet-and-spicy kick, while the Fun Guy pairs local mushrooms with ricotta and melted cheese. Saving a little room for tiramisu or an affogato is highly recommended.

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.

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