Putnam
Infamous traitor Benedict Arnold was in Putnam County (just across the Hudson River from West Point) when his treachery was discovered. He fled by water to a British ship at Croton Point in Westchester.
Rockland
Just outside Nyack, the little-known Clausland Mountain Tunnels were constructed during World War I as a training ground for the New York National Guard. Now abandoned, the graffiti-covered tunnels have spawned their own urban legends.
Orange
The Moodna Viaduct train trestle is the highest and longest railroad trestle east of the Mississippi River. It spans the Moodna Valley between Schunemunk Mountain and Woodcock Hill in Salisbury Mills and was constructed between 1904 and 1908 by the Erie and Jersey Railroad Line.
Ulster
The Tobias Van Steenburgh House was one of the few buildings in Kingston not burned by British troops in 1777. Theories on why it was spared range from the idea that the occupant was carrying on with a British officer to the theory that it was a tavern at the time and the troops were too busy drinking rum to set a fire.
Photo by Alan Light
Westchester
Paul Reubens (original surname Rubenfeld) — the actor, writer, and comedian best known as Pee-wee Herman — was born in Peekskill, though he later moved to Florida. Interestingly, his dad, Milton Rubenfeld, was one of the founding pilots of the Israeli Air Force after World War II.
Photo by Jennifer Barnhart
Greene
Dating from 1663, the Bronck House in Coxsackie is the oldest known building north of New York City and was built by Pieter Bronck, a relative of Jonas Bronck, the founder of the Bronx.
Photo by Matt Varney
Rensselaer
Troy is a world-renowned hot spot for Tiffany stained-glass windows. Among the places they can be found are the Troy Public Library, St. Paul’s Church, and St. Joseph’s Church. The latter has 42 of them!
Photo courtesy of Bain News Service
Albany
When Alfred E. Smith was New York State governor for eight years beginning in 1919, he installed a backyard zoo at the executive mansion in Albany that included a bear and monkeys that were known to escape and roam Capital City streets.
Columbia
In 1794, William Jenkins Worth, a future major general and hero in the Mexican–American War, was born on Union Street in Hudson. The city’s Worth Avenue is named after him, as is Fort Worth, Texas, and Worth Square in Manhattan, at the intersection of Broadway, 5th Avenue, and 25th Street. The Worth Monument in the square is the second-oldest major monument in NYC parks.
Dutchess
Gorgeous — though ominously named — Nuclear Lake in Pawling was the site of a plutonium spill in 1972 from an adjacent nuclear testing plant. Today, it’s home to a section of the Appalachian Trail and is considered safe (even enjoyable!) to visit.