Fairfield, Connecticut

This lonely point of land has guided ships for centuries, but the light you see now is a bit of an engineering marvel. In 1846, the original wooden tower was replaced. This new tower was one of the first prefabricated…

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…

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…

Built in 1847, this seaside hotel offers a glimpse into the golden age of coastal tourism. Back then, before air conditioning, city dwellers flocked to the shore for cool breezes and relaxation. The Milford Point Hotel,…

Check out that bridge! It’s more than just a way across the river; it’s a survivor from a time when railroads were king. Built in 1904, the Housatonic River Railroad Bridge, also known as the Devon Bridge, is a Scherzer…

Step back in time to the roaring twenties at this last surviving casino, where flappers danced and fortunes were won and lost. The Laurel Beach Casino was built in 1929. It's the last of what used to be seven casinos…

Out here in the middle of Long Island Sound, that lonely lighthouse marks a dangerous, shallow shoal. It's called Stratford Shoal Light, also known as Middle Ground Light. Built between 1875 and 1877, the lighthouse…

Before refrigerators hummed in every kitchen, places like this icehouse were vital. Built in 1908 by Ernest Kaatz, this wood-framed structure was the center of an ice harvesting operation on Kaatz Pond. Every winter,…

Imagine living on the same plot of land for over 350 years! That's the story of Boothe Memorial Park and Museum, claimed to be 'The Oldest Homestead in America'. The story starts with a house built around 1663. Fast…

Imagine sailing into Norwalk harbor back in the day, relying on this very light to guide you safely home. The Sheffield Island Light was built around 1868 after mariners complained that the existing light further east…

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…

This unassuming farmhouse was the sanctuary of a journalistic titan who dared to take on a powerful monopoly. This is Twin Oaks, the home of Ida Tarbell from 1906 until her death in 1944. Tarbell, a pioneering…

Pull over for a sec, because this unassuming house is a direct line to Milford's earliest days. This is the Buckingham House, built around 1725. It's been standing here for nearly 300 years! We know it was associated…

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

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…

This isn't just a pretty view; it's a place where history kept ships safe on Long Island Sound. Old Field Point Light was built in 1868 to guide vessels between Port Jefferson and Stony Brook harbors. Before that,…

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 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…

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 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 enduring one of the harshest winters of the Revolutionary War, right here. In the winter of 1778-1779, General Israel Putnam chose this location in Redding as the winter encampment for his Continental Army…

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…

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,…

Ever wondered what life was like on Long Island way back in the 1600s? Well, this unassuming house, the Brewster House, holds some serious secrets from those early colonial days. Originally built in 1665, it's one of…

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…

These unassuming walls witnessed the start of an extraordinary life. This is the David Humphreys House, birthplace of a Revolutionary War hero. Born here in 1752, David Humphreys rose to become a Colonel in 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…

This grist mill, built in 1699, not only ground grain but also defined a town boundary. Back in the late 17th century, folks realized they needed a reliable way to grind their grain, and this spot on Stony Brook seemed…

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 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…

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,…

Pull over for a second, because the history of this place is wild. Fairfield Hills Hospital, once a self-contained city for thousands of patients, has a story etched into its very walls. Construction started in 1929,…

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…

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.…

Step inside a time capsule at this general store, operating since 1857. Since before the Civil War, the Saint James General Store has been serving the community at the corner of Moriches and Harbor Hill Roads. It became…

Imagine navigating into New Haven harbor in the late 1800s without a reliable light! That's why Southwest Ledge Light is so important. Completed in 1877, this lighthouse marks the main channel into New Haven. It was one…

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…

You're driving through a place where time seems to slow down – welcome to the Miller Place Historic District! This area is a treasure trove of Long Island's past, showcasing how people lived centuries ago. Back in the…

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…

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,…

Ever wonder where the French army camped during the American Revolution? You're driving right through it! Right here, soldiers of Rochambeau's army rested and prepared, supporting American independence. This spot was…

Get ready to glimpse into a bygone era of opulence and mystery! You're approaching Tarrywile Park, home to the intriguing Hearthstone Castle. Built between 1895 and 1899, this grand structure was originally known as…

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…

Right here, in Danbury, is where one of America's most original composers got his start. The Charles Ives House, a simple wooden structure, was home to generations of Iveses, a family deeply involved in Danbury's…

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…

See that massive stadium ahead? That's the Yale Bowl, a true cathedral of college football. It’s more than just a place to watch a game; it’s a monument to the sport itself. Built way back in 1914, the Yale Bowl was 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…