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Pike County, created on March 26, 1814 from part of Wayne County, Pennsylvania, was named for General Zebulon Pike. Milford, Pennsylvania, the county seat, was incorporated in 1874 and named for Milford Haven of Wales.

At the time of European contact, the inhabitants were the Leni Lenape, later known as the Delaware Indians. The first European to visit to the region was Captain Arent Schuyler in 1694, sent by Governor Benjamin Fletcher of the colony of New York to determine whether the French were trying to enlist the Indians against the English. In 1696, governor Fletcher authorized a number of citizens of Ulster County to buy land from the Indians near New York. Descendants of those settlers became the first Europeans to settle in Pike County.

Early settlers included Nicholas Depui in 1725, Thomas Quick, who settled on the site of Milford in 1733, and Andrew Dingman in 1735, at what would become Dingmans Ferry. Settlers had good relations with the Indians at first; but as more settlers moved into the area, land disputes developed. The famous Walking Purchase of 1737 took in more than half of the present day Pike County and led to violence.

In the early 1800s, coal was discovered nearby in the area of present-day Carbondale, but an economical means of transporting the coal to New York was needed. A combination of a gravity railroad from Carbondale to Honesdale, and canal from Honesdale to New York was proposed. In 1823 the state of New York approved the building of the Delaware and Hudson Canal, a 108-mile (174 km) waterway between Honesdale and the Hudson River terminus near present day Kingston, New York. Work on the canal began in 1825 and was completed in 1828. The canal system proved profitable except where the barges crossed the Delaware. John Roebling proposed running the canal right over the river on an innovative suspension bridge/aqueduct, built in 1848; the suspension design called for only three piers (instead of the normal five), which allowed more room for ice floes and timber rafts to pass underneath. Three other suspension aqueducts were built for the canal.

The canal and aqueduct carried coal boats over the Delaware for the next fifty-one years. Then new New York and Erie Railroad proved cheaper and had the advantage of running in the winter when the canal froze over. By 1898 the canal was abandoned. Roeblings Delaware Aqueduct, possibly the oldest suspension bridge in America, is a National Historic Landmark.

In 1926, the Pennsylvania Power and Light Company built a dam on Wallenpaupack creek at Wilsonville for an electric generating plant. Construction of the dam required a crew of 2,700 men and took two years to complete at a cost of $1,026,000. Nearly a hundred landowners were bought out and farms, barns, and homes were razed or moved along with 17 miles (27 km) of roads and telephone lines and a cemetery. This project created the largest artificial lake in Pennsylvania, Lake Wallenpaupack.

Pike County had the fastest population growth of any Pennsylvania county between 1990 and 2000. Between 1990 and 2000, the county grew by 65.2%, and between 2000 and 2004, it grew 16.9%. Local leaders attribute the trend to the relatively low state and county taxes, affordable housing, and the ease of commute to New York City northern suburbs via Interstate 80 and Interstate 84.