Beekman Arms
Rhinebeck
From the sturdy stone walls and massive fireplace to the wide plank floors, the interior of “America’s oldest operating inn” simply exudes history. Open since 1766, the sprawling property—once called the Rhinebeck Hotel—has witnessed the full sweep of Hudson Valley history, from Continental Army soldiers practicing drills right on the front lawn to Hyde Park neighbor Franklin D. Roosevelt capping off his presidential campaigns with a speech from the tavern’s porch.
Tip
While the inn’s newly renovated guest rooms are outfitted with modern amenities, they still evoke colonial-era charm, designed with period-style wallpaper and four-post beds. Request Room 21 or 22: Legend says George Washington stayed there during the Revolutionary War. beekmandelamaterinn.com
D&H Canal Historical Society
High Falls
This small but fascinating museum highlights how changes in transportation and infrastructure shaped our region. From 1828–1898, the 108-mile Delaware & Hudson Canal fueled New York’s rise as the capital of industry and commerce. Exhibits include a model of a canal lock, a life-size cabin from a canal boat (the vessels were pulled by mules often guided by children, who were tasked with walking up to 20 miles per day), dioramas depicting life along the canal, and 19th-century paintings.
Tip
Take a walk along the old canal towpath and see five of the original locks that have been preserved. canalmuseum.org
Washington’s Headquarters
Newburgh
Learn about the region’s crucial role in the American Revolution at the Dutch-style farmhouse where Washington stayed after the Battle of Yorktown while waiting for a peace treaty to be signed. Purchased by New York State in 1850, the museum is the oldest publicly operated historic site in the United States, with an impressive collection of unique artifacts, including segments of the chain that Continental soldiers stretched across the Hudson to keep the British from sailing upstream.
Tip
Tour the newly restored “Tower of Victory.” Built in 1880, the belvedere offers captivating views of Mount Beacon across the Hudson River. parks.ny.gov
Clermont State Historic Site
Germantown
Seven generations of the influential Livingston family made their home at Clermont—French for “clear mountain,” after the site’s pristine views of the Catskills—including Robert Livingston, who helped draft the Declaration of Independence and administered the oath of office to George Washington in April 1789. This hidden gem of a museum tells the story of the rise of American wealth and power, often on the backs of enslaved Black laborers and impoverished tenant farmers.
Tip
Stop by the gift shop for Millerton-based tea-maker Harney & Sons’ special Clermont Blend, a mixture of eight black and white teas, crafted in honor of the Livingstons’ historic estate. friendsofclermont.org
West Point Foundry Preserve
Cold Spring
Don’t let the quiet trails and peaceful waterfalls fool you—this newly designated National Historic Landmark was once a bustling industrial landscape. Constructed after the War of 1812 on a site with access to timber, nearby iron mines, and a brook to power machines, the foundry built America’s first locomotive, cannons, and other weapons that helped win the Civil War. Transformed into an “outdoor museum” by Scenic Hudson, the 90-acre preserve is an overlooked treasure.
Tip
Don’t miss the 32-foot-tall tower used to test projectiles against Storm King Mountain across the river. Unexploded ordnance was found as late as 1999. scenichudson.org
Huguenot Street
New Paltz
Immigration to America didn’t start with Ellis Island, as this 10-acre historic district reminds us. Settled in the late 17th century by French-speaking Protestants fleeing religious persecution, the nationally recognized Historic Huguenot Street offers an immersive glimpse into a preserved streetscape with over 300 years of history, where visitors can explore seven historic house museums, a burial ground, a reconstructed church, and more.
Tip
Take a guided tour to gain insight into how the district helped shape local history. The Haunted Walking Tour will fascinate anyone captivated by spooky tales from the darker side of history. huguenotstreet.org
Thomas Cole National Historic Site
Catskill
For 15 years, the English-born painter (and founder of the Hudson River School) woke every morning and took in the rugged, sublime scenery from his porch that he made famous in his artwork. Now livened up by creative programming, surprising juxtapositions of Cole’s paintings with more contemporary pieces, and innovative uses of technology, this isn’t your typical house museum.
Tip
The Thomas Cole NHS is just one stop on the Hudson River School Art Trail. Continue on to the site of the former Catskill Mountain House, an easy walk from North-South Lake Campground, with views that Cole and other artists found inspiring. thomascole.org
Museum Village
Monroe
You don’t have to travel to Colonial Williamsburg or Mystic, Connecticut, to see what life was like in America before modern conveniences. Museum Village of Old Smith’s Cove presents hands-on exhibits and demonstrations of 19th-century life, from candle-making and printing to weaving and blacksmithing, along with recreations of a schoolhouse, drug store, log cabin, and other buildings. It also features one of only three complete mastodon skeletons in the world, unearthed a few miles away in 1952.
Tip
Check out the annual Civil War weekend every Labor Day, complete with uniformed reenactors and authentic weaponry demonstrations. museumvillage.org
Home of Franklin D. Roosevelt
Hyde Park
Descended from an old Hudson Valley family, the 32nd U.S. president was born in an upstairs bedroom at Springwood in 1882. The Italianate-style mansion later offered a sanctuary for the polio-stricken leader. “All that is within me cries out to go back to my home on the Hudson River,” Roosevelt once said. The house is meticulously staged as if the president just stepped out for one of his beloved drives through the countryside.
Tip
The onsite presidential library—the first in the federal system—offers many interesting exhibits, including one, open through 2024, that highlights FDR’s mixed record on civil rights. nps.gov/hofr
Wild Hudson Valley
Cairo
Ever wonder what life was like for the Hudson Valley’s indigenous Algonquin people before Europeans arrived? Find out at this 95-acre farm and nature sanctuary with engaging weekend programming devoted to native land-stewardship practices. Enjoy outdoor activities and educational hikes along a network of winding trails and consider extending your visit with an overnight stay at one of the furnished eco-campsites.
Tip
Sign up for the Wild Harvest Box subscription, a curated selection of native foods like mushrooms, nuts, and herbs (available for pickup May through November). A portion of the proceeds go toward Algonquin communities in the U.S. and Canada. wildhudsonvalley.com
Historic Westchester Homes Worth Visiting
John Jay Homestead
Katonah
Who: John Jay, the first chief justice of the United States, began construction on the home in 1787, the year the Constitution was drafted.
Style: Georgian
Fun Fact: Though Jay was president of an abolition society and signed a law as governor of New York that led the way to ending slavery in the state, he owned enslaved people at this estate. Some even ran away—“a measure,” the perplexed Jay wrote, “for which I cannot conceive of a motive.”
Thomas Paine Cottage
New Rochelle
Who: The famous writer of Common Sense—the first pamphlet to push for American independence, published in 1776—lived here from 1802–1806.
Style: Saltbox
Fun Fact: In 1809, Paine was buried on the grounds, but his remains were later dug up by a British admirer who wanted to rebury him in his native land. That never happened, and eventually Paine’s bones were lost.
Sunnyside
Tarrytown
Who: Washington Irving, the first famous American author best known for The Legend of Sleepy Hollow, expanded the colonial-era farmhouse into a more spacious home in 1835.
Style: Dutch Colonial Revival
Fun Fact: Irving fought (unsuccessfully) to prevent the New York Central Railroad from laying tracks along the base of his property. The “infernal alarum” of the steam-whistle left him in a “deplorable state of nervous agitation,” he wrote in 1850.
Kykuit
Sleepy Hollow
Who: Built for oil tycoon John D. Rockefeller Sr. in 1913, the estate was occupied by his grandson, Vice President Nelson Rockefeller, until his death in 1979.
Style: Classical Revival Georgian
Fun Fact: The elder Rockefeller didn’t care for the first “Kykuit” his architects and builders created. After it was destroyed by a fire in 1902, he hired two new architects—William Adams Delano and Chester Holmes Aldrich—to rebuild the home.
Armour-Stiner Octagon House
Irvington
Who: Financier Paul J. Armour modeled the eight-sided house in 1860 after a classical Roman temple. The remarkable dome—the only one in the world above an octagonal dwelling—was added a few years later by Joseph Stiner.
Style: Eclectic
Fun Fact: Poet and historian Carl Carmer lived here when he wrote The Hudson (1939), one of the best books written about the river’s history. Still a private residence, it is open for tours by appointment.
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