Everything Westchester is known for
Songs written about the waterways and highways that run near Westchester.
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.
One of America's most notorious prisons, built by inmates in 1826 on the banks of the Hudson River in Ossining, New York.
Philip Johnson's iconic residence, a transparent box of steel and glass, became one of the most influential buildings in modern architecture.
Amateur Night launched Ella James Brown and a young Michael Jackson. Harlem's crown jewel.
Hackensack NJ's tiny slider palace since 1946. Originally a 1939 World's Fair building. The griddle hasn't cooled down in decades.
The Queen of Soul Food in Harlem since 1962. Sylvia Woods built a dynasty on smothered chicken and collard greens.
88 stories, landmarks & places within ~20 miles — the same local lore RoadyGoat plays as you drive through.
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…
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 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…
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 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…
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…
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.
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 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 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 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…
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…
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 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…
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,…
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,…
Pull over for a moment and imagine a young boy gazing out these windows, dreaming of a world beyond the Hudson. This is the Edward Hopper Birthplace and Boyhood Home, where the seeds of an iconic American artist were…
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…
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…
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…
Pull over for a minute – this seemingly quiet spot holds a slice of Rockland County history. The Hopson-Swan Estate, now part of Tallman Mountain State Park, was developed between the 1850s and 1920s. The estate…
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…
Imagine composing some of America's most iconic music right here! This is the Aaron Copland House, where the legendary composer spent the last 30 years of his life. Copland, seeking respite and inspiration, began…
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…
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…
Prepare to be amazed by the Graham House, a Modern masterpiece seemingly growing out of the Connecticut bedrock. Manhattan art dealer Robert Graham commissioned architect Eliot Noyes to design this unique home,…
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 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…
Imagine standing where George Washington himself strategized during the Revolutionary War. This is the DeWint House, one of his headquarters. Built around 1700 by Daniel DeClark, the house later became the property of…
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…
This unassuming spot marks the end of a British spy's life and a pivotal moment in the American Revolution. Major John André, a British officer, was caught in 1780 conspiring with the American General Benedict Arnold to…
Pull over here for a second. This unassuming building played a part in one of the most daring escapes of the Revolutionary War. This is Putnam Cottage, but back then, it was Knapp Tavern, a popular spot on the Boston…
Ever wonder what it was like to cruise the waters around New York City a century ago? This is a clue. The MV Commander, built in 1917, was designed as a 275-passenger excursion boat. She originally ferried people…
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…
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…
Prepare to be amazed by a story of innovation, triumph, and, surprisingly, demolition. This area was once home to Edwin H. Armstrong, a radio genius who shaped how we communicate today. Armstrong, inventor of FM radio,…
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 this quiet corner of Connecticut buzzing with artists, writers, and ideas! This is the Bush-Holley House, a place that helped shape American Impressionism. Built around 1730, it transformed into a boarding house…
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…
Ever wonder how early commuter trains powered their way into New York City? The answer lies partly in what's left of the Cos Cob Power Station. Built in 1907, this Spanish Revival-style building was a crucial part 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…
Check out that bridge! It's more than just a way for trains to cross the Mianus River; it's a survivor from a bygone era of railroading. Back in 1904, the New York, New Haven and Hartford Railroad replaced an older,…
Right here, on this rocky point jutting into the Hudson, a daring midnight raid changed the course of the Revolutionary War. On July 16 07 1779, General Anthony Wayne led a surprise attack on the British garrison at…
Imagine navigating the Hudson River before GPS! This very spot, Stony Point, was a notorious hazard for ships. That's why they built Stony Point Light, the oldest lighthouse on the Hudson. In 1826, the US government…
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…
You're crossing a piece of history: the Riverside Avenue Bridge, Connecticut's only cast-iron bridge. Originally part of a larger bridge built in 1871 over the Housatonic River, it was moved here in 1895 when the…
This ornate Carpenter Gothic house is a well-preserved example of mid-1800s architecture. The William H. Rose House, located right here on Tomkins Avenue, was built for a wealthy local businessman. To give you an idea…
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…
Built in 1775, this stone house has witnessed the birth of a nation. The Isaac Naugle House, located on Hickory Lane, was built by a member of the Naugle family, likely Isaac, or his father Hendrick. Hendrick Naugle…
Likely built before 1778, this stone house stands as a silent witness to the American Revolution. The Tallman–Vanderbeck House, located on Piermont Road, was probably constructed by Cornelius Tallman. In the mid-19th…
Prepare to be amazed by a house that redefined modern architecture: the Glass House. Philip Johnson, a hugely influential architect, built this as his weekend retreat in 1948 and 1949. Johnson was deeply inspired by the…
Imagine Yonkers as a bustling colonial hub, and right here stood the center of it all. Philipsburg Manor Hall was the heart of a vast estate owned by the Philipse family, powerful figures in colonial New York. The…
Yonkers once hummed with the electric energy of trolleys, and this massive brick building was at the heart of it all. Built in the early 1900s, the Yonkers Trolley Barn housed and maintained the city's trolley fleet.…
Pull over for a second and imagine the roar of the crowd! Proctor's Theater in Yonkers was *the* place to be back in the day. Built between 1914 and 1916, it started as a vaudeville house, with live performances that…
Stamford, Connecticut, owes its modern character to a few key factors. Geographically, it sits on Long Island Sound with access to the Mianus River, a combination that made it attractive for early settlement and later,…
Yonkers is a city etched with history, a place where the echoes of the past resonate with the pulse of contemporary life. From its vantage point overlooking the Hudson River, its elevation offering sweeping views of New…
Built in 1765, this house offers a glimpse into the lives of early settlers in Bergen County. The Forshee-Van Orden House was built around 1765. It's a tangible reminder of the families who shaped this region in the…
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…
Imagine navigating these waters without a reliable guide – that's why the Stamford Harbor Ledge Light was built! Construction began in 1882 to mark the dangerous Chatham Rock. It was completed and lit in that same year.…
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…
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.…
Imagine stumbling upon a fairytale castle right here in Connecticut! That's the Marion Castle, also known as Terre Bonne, nestled on Shippan Point. Built around 1914, this French chateau-style home was the vision of…
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…
Pull over here for a quick look at a house that's seen centuries go by. This stone building, the Daniel Demarest House, gives us a real peek into colonial life in New Jersey.Back in 1724, Daniel Demarest built this…
Imagine shaping the future of women's rights from a quiet house in New Jersey! That's exactly what Elizabeth Cady Stanton did here in Tenafly. From 1868 to 1887, this was Stanton's home base. After years in Seneca Falls…
This unassuming spot was once Tenafly's vital link to the world, a bustling train station connecting this quiet town to the heart of New York City. For decades, the Erie Railroad's Northern Branch chugged through here,…
Right here in Darien stands the house that shaped the man who shaped America's national parks. Stephen Tyng Mather, the first director of the National Park Service, considered this house his true home, even though he…
Get ready to cross a bridge that was once a record-breaker! The Bear Mountain Bridge was the longest suspension bridge in the world when it opened. In 1924, folks celebrated the completion of this impressive structure,…
Believe it or not, that unassuming structure played a vital role in bringing clean water to a growing region. Back in 1881, the Hackensack Water Company purchased this site, then just an island in the Hackensack River,…
Philip Johnson's iconic residence, a transparent box of steel and glass, became one of the most influential buildings in modern architecture.
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…
This seemingly peaceful spot on the Hudson was once the site of a brutal and pivotal battle in the fight for American independence. Fort Montgomery, built in 1776, was a key American stronghold designed to control the…
Prepare to be amazed by Manitoga, a place where design and nature intertwine like nowhere else. This was the home and studio of Russel Wright, an influential industrial designer, and his wife Mary. From 1941 to 1961,…
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…
This unassuming stone house whispers tales of early life in Ridgewood. Built sometime between 1750 and 1760, the David Ackerman House offers a tangible connection to Bergen County's past. David Ackerman, likely the…
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…
You're driving along a road with history beneath its wheels! You're close to the Old Albany Post Road, a section of one of the oldest roads in America. Back in the mid-1600s, this route began as Native American trails.…
Imagine summering in a castle overlooking the Hudson! That's what life was like for railroad tycoon William H. Osborn and his family at Castle Rock, built in 1881. Osborn, president of the Illinois Central Railroad,…
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…
Ever wonder what life was like in a fancy Gothic Revival house? You're near one now! The Hermitage, right here in Ho-Ho-Kus, is a fascinating example of 19th-century architecture. Elijah Rosencrantz Jr. commissioned the…
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…
Imagine stumbling upon fragments of medieval Europe, transported piece by piece to upper Manhattan. That's essentially what The Cloisters is. In the early 1900s, American sculptor George Grey Barnard traveled through…
Pull over for a minute, because this unassuming house holds secrets from the birth of the nation. This is the Mandeville House, the oldest one standing in Garrison. Back in 1735, it was built as a simple farmhouse.…
Imagine a time when trains were the lifeblood of the Hudson Valley. Highland Falls Station, built in the 1880s, was a vital stop on the West Shore Railroad. Passenger trains regularly stopped here, connecting Highland…
Imagine the echoes of children's laughter bouncing off these walls; this historic schoolhouse once educated generations of Ridgewood kids. Built in 1895, the Beech Street School, now known as the Ridgewood Education…
Ever feel like you've stepped back in time? That's Garrison Landing for you. This whole district sprang up in the mid-1850s, right after the Hudson River Railroad laid its tracks. A local ferry company president built…
Built in 1707, this house offers a glimpse into early colonial life in New Jersey. The Terhune–Gardner–Lindenmeyr House, located right here in Paramus, was built way back in 1707. Over the years, it was home to families…
Imagine a Manhattan escape, a place where you can breathe and gaze out at the Hudson River. That's Hudson View Gardens. Built between 1923 and 1925, this cooperative apartment complex offered affordable urban housing to…