The history of New York City’s lost City Island monorail is a fascinating chapter in urban planning that illustrates both ambition and failure. In the early 20th century, City Island—located in the Bronx—was a vibrant maritime community with limited transportation connections to the rest of New York. To address this, a bold plan was conceived in the early 1910s to link City Island to the mainland via a monorail. The project, officially called the *Pelham Park and City Island Railroad*, was envisioned as a cutting-edge transportation solution using elevated rail technology. The system was designed to stretch over the wetlands of Pelham Bay Park, reducing the need for more invasive infrastructure.

Construction began in 1910, and by 1914, a prototype was operational. However, it was short-lived. The monorail faced significant technical issues, including mechanical failures and derailments. Public skepticism and political opposition grew, and with World War I diverting resources and attention, the project was abandoned. City Island residents continued to rely on other modes of transportation, such as streetcars and ferries. Today, the remnants of the monorail are long gone, but its story remains a curious reminder of New York’s ambitious—yet sometimes impractical—transportation experiments.