Pine Plains is a town in Dutchess County, New York, United States. The population was 2,473 at the 2010 census. The name is derived from the geographic character of the region. The hamlet of Pine Plains is on the north border of the county.

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

In 1907, Walter W. Law moved Briarcliff Farms from Briarcliff Manor, New York, to Pine Plains and sold the property in 1918. In 1916, New York banker Oakleigh Thorne and several business partners purchased large land parcels and began breeding Angus cattle still in the name of Briarcliff Farm. The farm was broken up into several smaller farms in the late 1940s, and most lasted until the early 1980s, closing due to property taxes and poor economic conditions. Berkshire Stud purchased 550 acres (0.9 sq mi) there, starting in 1983.

According to the United States Census Bureau, the town has a total area of 31.2 square miles (80.7 km²). 30.6 square miles (79.2 km²) of it is land, and 0.58 square miles (1.5 km²), or 1.89%, is water. The north town line is the border of Columbia County.

Three small lakes lie west of Pine Plains hamlet: Stissing Lake which is excellent for swimming, Thompson Pond which is dedicated to conservation for wildlife, and Twin Island Lake. Stissing Mountain, the town's highest point at 1,403 feet (428 m), is immediately to the west. It is formed of Precambrian gneiss that remains after numerous cycles of glaciation have scoured and reformed the surrounding terrain.

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