European settlers  first came to the area in the 1690’s, and the fertile valley became the home to many farms. Mahackmeck, later known as Port Jervis, was a small settlement located along and near the Old Mine Road (US Route 209) that carried early travelers southward from Kingston, New York. The small community was later sited as a boat basin and repair point along the Delaware and Hudson Canal. It became an important station on the waterway which was part of a larger 171-mile-long transportation system that shipped anthracite coal from northeastern Pennsylvania to New York City and New England. The small hamlet was named Port Jervis in 1827 by a group of citizens who wanted to honor the chief engineer of the canal, John B. Jervis, who was from Rome, New York, was then overseeing its construction.

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The next transportation system to dominate the landscape and eclipse the canal, was the New York and Erie Railroad, along with the Port Jervis and Monticello Railroad (which was later purchased by the New York, Ontario, & Western). The New York and Erie arrived in 1847, and successor companies continued to maintain a major presence here until the 1960s. In the early years of the twentieth century, several highways were built that passed through Port Jervis including US Routes 6, 209 and New York State Route 97, and then in the late 1960s, Interstate Highway Route 84. The city is now the southern most entry point for the Upper Delaware Scenic Byway, and once again is along a major flyway for the American bald eagle.