The Hamilton and Skaneateles Turnpike was an historical East-West toll road in Central New York State.

It roughly paralleled the Cherry Valley Turnpike, also called the Third Great Western Turnpike (now U.S. Rt. 20) to its north.

The old "Hamilton and Skaneateles Turnpike", ran west from Plainfield in norhwestern Otsego County, through the Madison County communities of Brookfield, East Hamilton, Hamilton, Eaton, Erieville, and New Woodstock. From there it continued west on basically the same path as the modern NY State Rt. 80 until it met up with the Cherry Valley Turnpike east of Otisco Lake

The Skaneateles Turnpike was incorporated under the name "The President and Directors of the Hamilton Skaneateles Turnpike" on April 2, 1805. In 1807 the company was authorized to intersect "The Great Western Turnpike" at any point east of west branch of the Unadilla River.

The current Skaneateles Turnpike, runs from Richfield Springs in north-central Otsego County to its intersection with Larkin Road between West Brookfield and East Hamilton in Madison County.