In the days before the nearby Wallkill River was rerouted to control flooding, it would often be an actual island for a period in the spring.

This rich soil is the result of constant flooding during the retreat of glaciers during the last ice age, about 12,000 years ago.

Farmers wanting to eliminate the constant threat of flood could not afford to pay the local mill owner to lower his dam, so they dug a series of ditches and canals to drain the "Drowned Lands.

[3] Pine Island was the southernmost terminus of the Erie Railroad's Goshen and Deckertown extension in 1867 and was the chief conveyor of agricultural products from the hamlet.

Just north of the hamlet, there was a junction with the Lehigh & New England Railroad (L&NE) who had trackage rights over the Erie from Pine Island Jct.

After the abandonment of the L&NE in 1961 and declining traffic levels, the Pine Island Branch was deemed unnecessary and ripped up.