Explore the Hudson River National Historic Landmark District, a history-rich area surrounding the town of Rhinebeck, New York. Sprawling for 22,205 acres (34.6 square miles), the district is the largest of its kind in the contiguous United States and lays claims to some of the most iconic landscapes and consequential historic sites in the country, including several notable estates once home to influential families like the Livingstons, Roosevelts, and Vanderbilts, as well as Hudson River School landscape painters like Frederic Church and Thomas Cole.

Revisit the extraordinary four-term presidency of Franklin Delano Roosevelt with tours of the Franklin D. Roosevelt Presidential Library and Museum and the nearby Roosevelt estate. The Library was the first Presidential Library in the U.S., initiated by F.D.R.'s precedent-setting donation of his papers to the government. Springwood, the home where Roosevelt was born and raised, saw many world luminaries during his terms of office, including Winston Churchill, who signed the historic A-bomb agreement there. The estate is also the site of Val-Kill, a favorite retreat for Eleanor Roosevelt and her family and friends, as well as her primary home following F.D.R.'s death in 1945.

See Rhinebeck through the eyes of one of its longest-established families, the Suckleys, who built a Queen Anne-style mansion on the Hudson in 1888, which today stands as the most significant example of Victorian architecture in the Hudson Valley. Now known as the Wilderstein Historic Site, the estate was home to three generations, including Margaret (Daisy) Suckley, a distant cousin and confidante of Franklin Delano Roosevelt. Through the years, they amassed a large collection of furniture, paintings, photographs, books, and more, which can be viewed during a guided tour of the home. Among the most notable artifacts are letters between Daisy and F.D.R., which illuminate the president's private thoughts. A fast friend and frequent companion of the president during his administration, Miss Suckley not only helped President Franklin Delano Roosevelt to establish his namesake library but also gifted him Fala, his beloved black Scottish terrier.

Follow in the footsteps of two of New York's most influential families, the Livingstons and the Vanderbilts, with a visit to their palatial estates. Prominent Hudson Valley landowners since the 17th century, the Livingstons can count signers of the U.S. Declaration of Independence and Constitution in their number, as well as, more recently, First Lady Eleanor Roosevelt and Presidents George H. W. Bush and George W. Bush. Today, along with the Georgian-style Clermont Manor, which was home to seven generations of Livingston families across more than two centuries (including Margaret Beekman Livingston, a member of the family for whom Beekman Arms is named), travelers can also visit other Livingston estates like the Federal-style Montgomery Place and the Beaux-Arts-style Staatsburgh State Historic Site. Another stunning example of Beaux-Arts architecture that is not to be missed is the Vanderbilt Mansion. With its opulent furnishings and ornate ceilings, this 54-room Gilded Age icon offers a glimpse into the life of one of the wealthiest families in American history.