In the tiny hamlet of Wassaic, contemporary art has found an unlikely home inside a seven-storey former grain elevator. The Wassaic Project fills historic Maxon Mills with exhibitions by emerging artists, while studios, artist residencies and public artworks spill into the surrounding village. 

Built in 1782 as a travellers’ tavern, Stissing House has been feeding and watering Pine Plains for centuries. Today, chef Clare de Boer gives the historic rooms a lively country-tavern spirit, with seasonal cooking shaped by the surrounding farms. Settle by the fire for roasted oysters, a generous slice of venison pie or something sweet.

Built for wealthy couple Ogden and Ruth Livingston Mills, this 65-room Beaux-Arts mansion is dressed in French-inspired interiors, original furnishings, elaborate fireplaces and enough decorative detail to keep you looking. Outside, the grounds stretch towards the Hudson River, with the Catskill Mountains on the horizon. Book a guided tour to peek into the lives of the family who entertained New York’s elite here.

The house of Frederick and Louise Vanderbilt in the late 1890s, this National Historic Site is a Gilded Age triumph of marble, exotic wood panelling, French tapestries and rich velvet, looking out across manicured lawns towards the Hudson River and Catskill Mountains. Save time for a stroll through the formal gardens, where European-inspired landscaping gives the grounds their own grand entrance.