Perched atop the prettiest bluffs of the Hudson River’s undulating, tree-covered right bank, with sweeping views of the majestic waters below, is America’s most astounding collection of great estates, many built in the 19th century by the rich and powerful as high-status getaways. Others, like the Roosevelt family’s Springwood in Hyde Park and Clermont in Germantown, served as the permanent residence for the Hudson Valley’s most prominent old money families. Fortunately, descendants took great pains to see that the estates survived, and the houses remain furnished much as they were, as though the families would be walking through the front door at any moment.
Among the area’s pleasure palaces, none is more showy than the beaux arts Vanderbilt Mansion in Hyde Park, built in 1895 by Frederick William Vanderbilt, heir to the great shipping and railroad fortune. (The site was chosen for its proximity to the Roosevelts, though the Vanderbilts used the flamboyantly opulent 54-room limestone mansion for just a few weeks in spring and fall. For the rest of the year, a staff of 60 was left to care for the house and gardens, for which the estate is still known.)
Lyndhirst is an imposing gray stone Gothic Revival estate bought in 1880 by “robber baron” Jay Gould, the fabulously wealthy railroad magnate and stock manipulator. Destgned by the master of Gothic Revival, Andrew Jackson Downing, and built in 1838, the impressively grand home has a dining room that looks like a medieval banquet hall, along with Gilded Age must-haves like Tiffany stained glass windows and faux-finish paneling.
Two of the region’s greatest estates are also on the Hudson Valley Art Trail: the Rockefellers’ 1913 country home, Kykuit (its name means “lookout” in Dutch and refers to its hilltop position), and Olana, the enchanting Moorish fantasy palace where Frederic Church made his home and took his inspiration.
A quintessential representation of Hudson Valley old money is the Livingston family, whose prominence began when Robert Livingston became the first Lord of Livingston Manor, a vast area that comprised the lower third of Columbia County. His son (also Robert) began construction of a brick Georgian-style home in 1730, and though Clermont has gone through many changes (including a complete rebuilding after being burned by the British in 1777), it remains a glimpse into nearly three centuries of wealth, impeccable taste, and political prominence.
Not far from Clermont, just outside Rhinebeck, is Montgomery Place, erected in 1804 by another member of the family, Janet Livingston Montgomery, in honor of her husband, Richard, the first officer killed in the Revolutionary War. The open porch of this elegant Classical Revival mansion (with dramatic views of the river and the Catskills beyond) was the first “outdoor room” in America. Scenic trails wend through the 434-acre estate, which still grows apples, peaches, plums, apricots, and black raspberries that can be purchased at the estate’s farm stand on River Road.
Old and new money merge in Staatsburgh just north of Hyde Park at a 25-room Greek Revival house on 334 acres, inherited in 1894 by Ruth Livingston Mills, who was married to investment capitalist Ogden Mills. They expanded it into a 65-room beaux arts extravaganza for entertaining friends in the fall, and its imported 17th- and 18th-century French interiors, gilded furniture, and Baccarat crystal bathroom accessories are just as they were when their son donated the property to New York Stale in 1938.
While all the grandeur is fun to look at, it’s easier to imagine die good life at Sunnyside, the fairytale confection of turrets and gingerbread that was the home of Washington Irving, author of “The Legend of Sleepy Hollow” and “Rip Van Winkle.” Originally a two-room farmer’s collage, the home was fancifully expanded with Tudor-style clustered chimneys, Dutch stepped gables, Gothic windows, a small piazza, and, later, a Spanish-style tower. Outside the front door, the wisteria Irving himself planted continues to bloom each spring, while the trails he laid out on the 27-acre estate are still a perfect place for a stroll by the river.
The nearby Sleepy Hollow Cemetery, where Irving set his tale of Ichabod Crane and the Headless Horseman, is especially popular around Halloween. The Dutch began burying their dead here as early as 1650, and today the cemetery holds more than 39,000 earthly remains, including those of Irving himself and many of the wealthy empire (and great estate) builders, including Andrew Carnegie and William Rockefeller.