10 Historic Hotspots to Visit for a Look Into the Hudson Valley’s Past

From houses and hotels to parks and farms, here are 10 of the most interesting places to visit to learn more about the origins of our region—and the nation.

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.

Beekman Arms
Photo courtesy of Beekman Arms

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

Beekman Arms
Photo by Noel McGrath

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.

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D&H Canal Historical Society
Photo by Bill Merchant

Tip

Take a walk along the old canal towpath and see five of the original locks that have been preserved. canalmuseum.org

D&H Canal Historical Society
Photo by Bill Merchant

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.

Washington’s Headquarters
Photo courtesy of the NYS Office of Parks, Recreation & Historic Preservation

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

Washington’s Headquarters
Photo courtesy of the NYS Office of Parks, Recreation & Historic Preservation

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.

Clermont State Historic Site
Photo courtesy of the NYS Office of Parks, Recreation & Historic Preservation

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

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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.

West Point Foundry Preserve
Photos by Robert Rodriguez / Courtesy of Scenic Hudson

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

West Point Foundry Preserve
Photos by Robert Rodriguez / Courtesy of Scenic Hudson

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.

Historic Huguenot Street
Courtesy of Historic Huguenot Street

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.

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Thomas Cole National Historic Site
Photo by Rachel Stults

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.

Museum Village
Photo courtesy of Museum Village

Tip

Check out the annual Civil War weekend every Labor Day, complete with uniformed reenactors and authentic weaponry demonstrations. museumvillage.org

Museum Village
Photo courtesy of Museum Village

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

Home of Franklin D. Roosevelt
Bywd Urbin / Courtesy of The National Park Service

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.

Wild Hudson Valley
Photo courtesy of Wild Hudson Valley

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

John Jay Homestead
Courtesy John Jay Homestead

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

Thomas Paine Cottage
Courtesy Thomas Paine Cottage

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

Sunnyside
Courtesy of Historic Hudson Valley

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

Kykuit
Photo by Jaime Martorano

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

Armour-Stiner Octagon House
Photo by Sean Hemmerle

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.

Related: Every Direct Flight You Can Take From Albany International Airport

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