Stamford, Connecticut

Imagine life in early Colonial Connecticut. This unassuming saltbox house, the Thomas Lyon House, stands as a testament to those times. Built around 1739, it was home to Thomas Lyon, grandson of one of Fairfield…

This unassuming bridge is more than just a way for trains to cross the Norwalk River; it's a living piece of history, still working hard after over a century. Built in 1896, the Norwalk River Railroad Bridge, also known…

Prepare to be wowed! You're near a house that helped launch the career of a modern architecture giant. Marcel Breuer, fresh from the Bauhaus school in Germany, designed this house for his family in 1947. It's a stunning…

Imagine colonial life in New York at the Bush-Lyon Homestead, with sections dating back to 1720! This house started as a simple, one-and-a-half story home. Over time, around 1800, it grew. A kitchen wing was added to…

Step back in time inside this opulent 62-room mansion built for a railroad tycoon during the Gilded Age. The Lockwood–Mathews Mansion, a stunning example of Second Empire style, was completed in 1868. It was…

Ever wish you could've seen the Stones in a more intimate venue? Well, you might have if you'd been at the Capitol Theatre in Port Chester back in the day! Built in 1926, this place was originally a movie palace…

That little white tower out on the water? That's Peck Ledge Light, and it's been guiding ships safely through these waters since 1906. It's a classic 'sparkplug' lighthouse, designed to be sturdy and visible. Before…

Get ready to step back in time to an amusement park that's been thrilling families for almost a century: Playland! Back in 1927, Westchester County decided to build a public amusement park on the Long Island Sound. It…

Pull over here for a sec; this unassuming red building witnessed the birth of a nation! The Smith Tavern, right here in Armonk, served as a crucial gathering place during the Revolutionary War. Local militia used this…

Get ready to cross Connecticut's oldest surviving movable bridge, built way back in 1884! This isn't just any old span; it's a piece of living history carrying Route 136 over the Saugatuck River in Westport. Before this…

Take a moment to reflect on the lives of African Americans who shaped this community, resting here at the Rye African-American Cemetery. In 1860, the Underhill family donated this land, ensuring it would forever be a…

This unassuming spot marks a legacy of bravery on the Long Island Sound. Coast Guard Station Eatons Neck is the oldest Coast Guard Station in New York. Founded in 1849 by the New York Lifesaving Benevolent Association,…

Imagine navigating these waters before GPS, relying only on the steady beam from Eatons Neck Light. Built in 1798, this lighthouse was designed by John McComb, Jr., the same architect who later worked on New York City…

Ever wonder where America's yachting tradition took sail? You're near one of its birthplaces. The Seawanhaka Corinthian Yacht Club is among the oldest yacht clubs in the Western Hemisphere. Founded in 1871, the club…

Philip Johnson's iconic residence, a transparent box of steel and glass, became one of the most influential buildings in modern architecture.

Guiding ships since 1857, this lighthouse stands as a sentinel at the entrance to Huntington Bay. It's the Huntington Harbor Light, originally called Lloyd Harbor Lighthouse. In 1857, they established a lighthouse here.…

You are at Sagamore Hill in Oyster Bay, New York, Theodore Roosevelt's home from eighteen eighty-five until his death in nineteen nineteen. Twenty-three rooms on one hundred fifty-five acres overlooking Oyster Bay, and…

Just a stone's throw from Theodore Roosevelt's beloved Sagamore Hill stands another piece of Roosevelt history: the Yellowbanks estate. Built in 1881, Yellowbanks was commissioned by James A. Roosevelt, Theodore's…

Right here, in unassuming White Plains, lived a musical rebel! This is the former home and studio of Percy Grainger, an innovative composer and pianist who pushed the boundaries of music.Grainger, an Australian-born…

Pull over a sec; this is where you can learn about the Christeen, the oldest oyster sloop in the United States! She's a real piece of Long Island history. Built in 1883 in Glenwood Landing, the Christeen spent years…

Imagine a place where justice echoed for over a century – that was the Westchester County Courthouse Complex. The complex evolved over time, starting with a courthouse built in 1857. Later, the Hall of Records was added…

Picture this: a pharmaceutical king decided he needed a castle, and that's exactly what he built right here. Tour this massive 40-room mansion built in the style of a medieval French château for a pharmaceutical…

This unassuming house is a powerful symbol of resilience. The Skinny House in Mamaroneck was built in 1932 by Nathan Thomas Seely, an African-American carpenter. He lost his home to foreclosure and his company to…

Imagine sailing across the Atlantic to build a new life – that's exactly what Captain Thomas Fleet did, right here near Huntington. Around 1660, Captain Fleet arrived from England with his family and his own ship. He…

Prepare to be moved by a place where love for our animal companions is etched in stone: Hartsdale Pet Cemetery. In 1896, a New York City veterinarian, Dr. Samuel Johnson, allowed a grieving woman to bury her dog on his…

Prepare to be transported to a world of Gilded Age extravagance! This is the Vanderbilt Museum, once the magnificent estate of William Vanderbilt II. William Vanderbilt II, grandson of Cornelius Vanderbilt, inherited a…

This unassuming church tells a powerful story of faith and community in the face of adversity. Bethel AME Church was cofounded in 1843 by Peter Crippen and Nelson Smith. The original church building, the one you see…

Prepare to witness architectural history! Right here, nestled in Weston, stands a testament to the genius of Ludwig Mies van der Rohe: the Morris Greenwald House. Morris and Rose Greenwald commissioned Mies van der Rohe…

This unusual octagonal house, built in 1859, stands as a unique example of architectural experimentation. The Prime–Octagon House, located on Prime Avenue in Huntington, New York, was completed in 1859. It sits right…

Ever swung an axe? Someone here might have made it. This area was once the heart of the Bradley Edge Tool Company, a thriving industrial village in the mid-1800s. The company was founded in 1834 and produced a variety…

Pull over here for a minute. This simple building played a huge role in the fight for freedom. The Chappaqua Friends Meeting House, built in 1753, became a vital station on the Underground Railroad, offering refuge to…

Ever wondered where a Founding Father kicked back after shaping a nation? This is it: John Jay Homestead. John Jay, one of the authors of the Federalist Papers and the first Chief Justice of the United States, called…

Imagine living in a house that's seen over three centuries pass! That's the story of the John Wood House, right here in Huntington Station. Built around 1704, this wasn't just a house; it was a home, built in the…

You're near a piece of land with a wild history, dating back to before the Revolutionary War. This is the site of the Romer-Van Tassel House. The original Romer family house stood here when, in 1780, they played a part…

Check it out, you're near the Bronson Windmill, a unique survivor from a time when windmills dotted this whole area. Frederic Bronson, who owned a big estate around here, had this windmill built in 1893 and 1894. It was…

That unassuming building you're approaching? It was once the summer home of famed architect Cass Gilbert, who designed some impressive additions to it. During the Revolutionary War, this tavern was right in the thick of…

Prepare to be amazed by the stained glass masterpieces housed within the Union Church of Pocantico Hills. John D. Rockefeller Jr., wanting to improve the community near his family's estate, Kykuit, funded the church's…

Prepare to be transported back to the Gilded Age. Hempstead House stands as a testament to the immense wealth and extravagant lifestyles of America's elite. Originally commissioned by Howard Gould, son of railroad…

Pull over here and you're standing near the place where a global movement began! This is Stepping Stones, the home of Bill Wilson, co-founder of Alcoholics Anonymous. Bill and his wife Lois lived here for decades. Bill…

You're approaching something truly special: the oldest private songbird sanctuary in the entire US! It all started with Mabel Osgood Wright, a passionate bird lover who, in 1914, decided to create a haven for our…

Step into the world of Frederic Remington, the famous painter and sculptor who captured the spirit of the American West. This is where he spent the last few months of his life. Remington and his wife, Eva, designed this…

Legend says Execution Rocks Light is named for the executions that took place on these rocks, and some say it's haunted. While the name's origin isn't definitively known, a popular theory suggests that during colonial…

Ever wonder where unimaginable wealth goes? Right here. Kykuit, perched high above the Hudson River, was the Rockefeller family estate for generations. John D. Rockefeller, the oil tycoon, had this 40-room mansion…

Pull over for a second. You're passing a piece of New Rochelle history, a house that's seen centuries go by. This is the Lispenard–Rodman–Davenport House, and it's the oldest residential building in the whole town.…

Prepare to be transported to a world of Jazz Age glamour – you're approaching Oheka Castle, rumored to be the inspiration for F. Scott Fitzgerald's *The Great Gatsby*. Otto Hermann Kahn, a wealthy financier,…

Guiding ships since the 19th century, Sands Point Lighthouse stands as a sentinel overlooking the Long Island Sound. It's the fourth lighthouse established on Long Island. This stone tower was first lit in 1809. Samuel…

Pull over for a second – right here, in this unassuming corner of Westchester, lived a woman who changed the course of American history: Carrie Chapman Catt. From 1919 to 1928, this Arts and Crafts-style house, Juniper…

Prepare to be amazed by Leland Castle, a Gothic Revival masterpiece that whispers tales of Gilded Age extravagance. Constructed between 1855 and 1859, this castle was the country estate of Simeon Leland, a wealthy New…

The Old Dutch Church of Sleepy Hollow, built around 1685, and the adjacent cemetery inspired Washington Irving's 'The Legend of Sleepy Hollow' in 1820.

Prepare to be inspired! This is Villa Lewaro, the stunning estate built by Madam C.J. Walker, one of the first self-made female millionaires in America. Madam Walker, a successful entrepreneur in the hair care industry,…

Prepare to be haunted – in the best way possible! Sleepy Hollow Cemetery is more than just a graveyard; it's the final resting place of literary giants and titans of industry. Originally founded as Tarrytown Cemetery in…

Prepare to be transported back in time as we approach Lyndhurst, a stunning Gothic Revival mansion overlooking the Hudson River, and once owned by the infamous railroad tycoon, Jay Gould. But its story begins long…

Imagine crafting tales so captivating, they define American folklore! That's the legacy of Washington Irving, and this is Sunnyside, the enchanting home he built and cherished. Irving, already a celebrated author,…

Behold the unique Armour-Stiner House, an octagon-shaped Victorian mansion that stands as a testament to architectural eccentricity. This isn't your typical suburban home! Built between 1859 and 1860, the house was…

Catch a show at this beautifully preserved 1921 Spanish Revival movie theater! The Picture House, originally known as the Pelham Picture House, opened its doors in 1921. It was designed in the Spanish Revival style, a…

Right here is where the legendary Walt Whitman began his journey. He was born in this farmhouse on May 31 1819. The house was built by his father, Walter Whitman, Senior, around 1810. The Whitman family lived here until…

Imagine navigating the Hudson River at night without a reliable guide. That's why Tarrytown Light, also known as Sleepy Hollow Light, was built. In the mid-1800s, the need for a lighthouse to warn ships away from…

Pull over for a second; you're about to see two estates that tell a century-long story of Long Island wealth and artistry. These are the Clayton and Cedarmere Estates, now listed together on historical registers.…

This unassuming building holds the secrets of a financial giant! Metropolitan Life Insurance, one of the largest insurance companies in America, built this Hall of Records back in 1906 to house its growing mountain of…

This unassuming spot was once vital to the growth of Yonkers, providing clean water to its rapidly expanding population. In 1876, as Yonkers boomed, the Tuckahoe Road Pumping Station was built. It was expanded before…

Pull over for a pint of history! This unassuming building, known as the Jug Tavern, was right in the thick of things during the American Revolution. Back then, this spot was on the Albany Post Road, the main drag, and…

One of America's most notorious prisons, built by inmates in 1826 on the banks of the Hudson River in Ossining, New York.

Ever wonder where the first photos of the moon clear enough to identify features were taken? You're getting close! This is the site of the Henry Draper Observatory. Henry Draper, a physician and astronomer, built this…

Imagine the Hudson River School's vibrant landscapes coming to life right here! This is Ever Rest, the home and studio of Jasper Cropsey, a master of that iconic American art movement. Cropsey, already a successful…

Ever wonder what a perfectly preserved slice of small-town America looks like? You're driving through it right now! Welcome to the Downtown Ossining Historic District, a remarkably intact example of a late 19th and…

Imagine learning in this one-room schoolhouse built in 1790! It's the Umpawaug District School, and it's the only one-room schoolhouse still standing in Redding. Kids from this area walked here every day to learn their…

Imagine soldiers drilling right where you're standing! Seaside Park's story begins not with picnics and beaches, but with war. Back in 1846, as the Mexican-American War heated up, the State of Connecticut established a…

Imagine lavish parties echoing through sculpted gardens – that's the legacy of Untermyer Park. Samuel Untermyer, a prominent lawyer, transformed his 1916 estate, Greystone, into a horticultural masterpiece. He hired…

Imagine Gatsby throwing a party – that's the vibe of Old Westbury Gardens! This place was built as a lavish country estate for a wealthy family during America's Gilded Age. John Shaffer Phipps, an heir to a massive…