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Bradford Lee Gilbert, a prolific railroad architect who is also often credited with designing New York City’s first skyscraper, designed this passenger station in a Richardsonian Romanesque style that you can see characterized in its thick masonry walls, rounded arches over windows and doors, and rough faced stone. The building was constructed in 1893 and included everything from a waiting room and ticket office to restrooms and a popular restaurant. It saw plenty of traffic in its early days from New York City tourists heading to the Catskill and Oneida Lake, but the railroad would eventually go under in 1957 as transportation trends changed to cars and highways. Since then, it’s housed everything from an art studio to a nightclub, but in recent days, it was slated for demolition in order to make way for a new health center, but due to financial troubles with the health center, it sounds like the city will re-inherit the building.

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7 Low Ave, Middletown, NY 10940, USA

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