The town was part of the Little Nine Partners Patent of 1706. The town was first settled around 1740 by Moravian missionaries. The Town of Pine Plains was formed from the Town of North East in 1823.

The north town line is the border of Columbia County, New York. Three small lakes lie west of the community of Pine Plains: Stissing Pond which is excellent for swimming, Thompson Pond which is dedicated to conservation for wildlife, and Twin Island Lake, the largest out of the lakes lie in the center of the town.

The most prominent physical feature is Stissing Mountain which at 1,403 ft (428 m). elevation, towers over the local area. The mountain is formed of pre-cambrian gneiss that remains after numerous cycles of glaciation have scoured and reformed the surrounding terrain.

The town has recently been battling NYC speculators about zoning restrictions through the zoning contingencies of former town supervisor Scott Chase.

Communities and locations in Pine Plains: