A Historian’s guide to visiting the Hudson Valley

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Franklin D. Roosevelt’s library at the Roosevelt home in Hyde Park. (Wikimedia Commons/CC BY-SA 2.0)

The Hudson Valley is a gem of the Empire State and is full of history. From presidents to music fests, read on for a plan to explore.

Every New Yorker has heard of the Hudson Valley. Whether it’s the scenic natural beauty found just a short drive from New York City, or the area’s many celebrated wineries, restaurants, and wedding venues, there’s plenty for everyone to love. But what if you’re a history buff? Well, then you’re really in for a treat!

As a historian, the Hudson Valley is one of my favorite places in New York. Not only is it a beautiful part of the state, but it’s also jam-packed with fascinating historical sites to explore. Best of all, Hudson Valley history is diverse; whether you’re most interested in Presidential hideaways which were once the sites of international diplomatic events, or you’re a music lover who wants to retrace the footsteps of some of America’s artistic legends, there’s a little something for everyone.

So, without further delay, let’s have a look at the best Hudson Valley history spots for a New York getaway.

Franklin D. Roosevelt’s library at the Roosevelt home in Hyde Park. (Wikimedia Commons/CC BY-SA 2.0)

Hyde Park on the Hudson and a presidential (and royal) history

Not to be confused with Hyde Park in London—though both sites do have connections to the British Royal Family! Hyde Park on the Hudson is the town where you can find the former home of President Franklin Delano Roosevelt. Today, the house and grounds are part of the Home of Franklin D. Roosevelt National Historic Site, managed by the National Park Service, along with the FDR Presidential Library and a museum with exhibits on Roosevelt’s presidency, his relationship with his physical disability, and more.

When visiting the Roosevelt home, be sure to join in one of the tours led by Park Rangers throughout the day. The tour guides often have fun tidbits to share about the entire Roosevelt family, including how FDR’s mother, Sara Delano Roosevelt, once bragged that their branch of the family was “better looking” than Teddy Roosevelt and his closer relatives—and how Eleanor Roosevelt, Teddy’s niece, didn’t take kindly to that comment!

What’s better than one Roosevelt historic site? Two of them! Near the Roosevelt home is Val-Kill, now the Eleanor Roosevelt Historic Site, although both Eleanor and Franklin did live there at times. Val-Kill was originally a furniture factory, but became a private retreat for Eleanor, and offers tours today.

And as for that Royal Family connection? It was at the Hyde Park home where Roosevelt hosted King George VI and his wife Queen Elizabeth, the first British monarchs to visit the United States. Famously, the Roosevelts caused controversy when they served the royal visitors a picnic lunch of hot dogs—but the King, who had never eaten a hot dog before, enjoyed his so much that he asked for seconds!

Exterior of the pool house at the Vanderbilt Mansion National Historic Site. (Wikimedia Commons/CC BY-SA 4.0)

Grand legacies at Lyndhurst and the Vanderbilt Mansion

Feeling up for some Gilded Age splendor after all that Presidential history? While the characters on the TV show “The Gilded Age” tend to stick to Newport and New York City, the Hudson Valley is home to a real-life Gilded Age legacy. Two of the best places to enjoy it are at Lyndhurst and the Vanderbilt Mansion.

Since you’re already in Hyde Park, your first stop is the Vanderbilt Mansion National Historic Site. Fun fact: the mansion was actually granted its National Historic Site Status in 1940, during FDR’s presidency! Today, visitors can tour three stories of the mansion, all furnished in the full splendor that befits a family whose name is now synonymous with the Gilded Age.

You’ll also hear about the Vanderbilt family, including the rowdy “Commodore” Vanderbilt who founded the family fortune, and his admittedly more conventional son, Frederick, who built the mansion in Hyde Park after purchasing the eighteenth-century estate and demolishing the older, no longer safe to inhabit, house standing on it.

Then, it’s on to Lyndhurst, which describes itself as “where the Hudson Valley begins.” Beyond being a gateway to the area, Lyndhurst is a Gothic Revival architectural masterpiece, and tours there emphasize its historical significance throughout the nineteenth and into the twentieth century, as ownership passed among three separate families until it was finally left as a museum by the philanthropic Anna Gould, a French duchess by marriage.

An artistic excursion to Olana

Olana was once the home of celebrated painter Frederic Edwin Church, who was an important figure in the Hudson River School artistic movement, known for landscape painting. Given that it was the Hudson River School, it only makes sense that there’s an art history spot to visit in the Hudson River Valley. Today, Olana is a State Historic Site, and you can explore the 250-acre property, with Church’s mansion and art collection at its centerpiece. 

As a visitor, you’ll be walking in the footsteps of many others, including Mark Twain, who was awed by the natural and man-made beauty he witnessed there. You can also view the rotating temporary exhibitions on the house’s second floor, and even bring a four-legged friend; dogs are permitted on the property as long as they remain leashed.

Beacon and Woodstock, New York’s musical heartlands 

There’s no reason that a history buff can’t also be a music lover, and there are spots in the Hudson Valley that are must-visits if you’re both.

First stop, Woodstock! The town was founded in the eighteenth century, but is best known for the musical festival that took place nearby (though technically in the town of Bethel) in 1969. In fact, the town of Woodstock was actually the home of the Woodstock Sound-Outs, mini festivals that predated the famous large one, and lasted a year longer.

Today, Woodstock is still home to a proud artistic community and to Byrdcliffe Arts and Crafts Colony, America’s oldest arts and crafts colony, dating back to 1902, where you can view exhibitions and attend events. You can also enjoy some live music at one of Woodstock’s many venues, or even watch a movie at the Tinker Street Cinema, which is housed in a historic church and served as a rehearsal space for Jimi Hendrix before the 1969 festival.

Finally, folk music lovers shouldn’t skip a trip to Beacon, which may not have as famous a name as Woodstock, but for over three decades, was home to folk music legend Pete Seeger and his wife Toshi. Today, a riverfront park in Beacon is named for the famous couple, and the Beacon Sloop Club, which they founded, offers free weekend sailing excursions on the Woody Guthrie, a replica of a historic 18th-century sloop, named for another folk music legend and Seeger’s beloved friend.

There’s no shortage of fun and fascinating historical attractions in the Hudson Valley, so don’t try to fit everything in on a single visit! This part of the Empire State has been full of things to experience for centuries, and you can always come back for more!

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