The transportation system of New York City is a cooperation of complex systems of infrastructure. New York City, being the largest city in the United States, has a transportation system which includes the largest subway system in the world, measured by track mileage; the world's first mechanically ventilated vehicular tunnel, and an aerial tramway. Through prolonged use, and a distinct history of events, the infrastructure now faces increasing problems in functionality, dependability, and funding. The history of New York City's transportation system began with the Dutch port of Nieuw Amsterdam. The port had maintained several roads; some were built atop former Lenape trails, others as "commuter" links to surrounding cities, and one was even paved by 1658 from orders of Petrus Stuyvesant, according to Burrow, et al. The 19th century brought changes to the format of the system's transport- a street grid by 1811 (see the Commissioners' Plan of 1811), as well as an unprecedented link between New York and Brooklyn, then separate cities, via the Brooklyn Bridge, in 1883. The Second Industrial Revolution fundamentally changed the city – the port infrastructure grew at such a rapid pace after the 1825 completion of the Erie Canal that New York became the most important connection between all of Europe and the interior of the United States. Elevated trains and subterranean transportation ('El trains' and 'subways') were introduced between 1867 and 1904. In 1904, the first subway line became operational. Practical private automobiles brought an additional change for the city by around 1930, notably the 1927 Holland Tunnel. With automobiles gaining importance, the later rise of Robert Moses was essential to creating New York's modern road infrastructure. Moses was the architect of all 416 miles (669 km) of parkway, many other important roads, and seven great bridges.

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