Beginning in 1916, and for a few years after that, New Ashford had the distinction of casting the first vote in United States Presidential Elections (as Dixville Notch, New Hampshire does today).

Following the ratification of the Nineteenth Amendment the New Ashford poll was where Ms. Phoebe Jordan became the first woman to vote in a national election on November 2, 1920.

New Ashford is bordered by Williamstown to the north, Adams to the east, Cheshire to the southeast, Lanesborough to the south, and Hancock to the west.

New Ashford sits in a small natural valley within the Taconic Mountains (popularly grouped with the Berkshires).

To the east, Mount Greylock State Reservation rises, with the mountain itself peaking just northeast of the town.

The Mount Greylock Scenic Drive crosses through the eastern part of town, on its way to the peak, as does the Appalachian Trail.

To the west, Brodie Mountain runs along the western border of town, peaking in neighboring Hancock.

[20] The town is patrolled by the Fourth (Cheshire) Station of Barracks "B" of the Massachusetts State Police.

Massachusetts is currently represented in the United States Senate by Elizabeth Warren and Ed Markey.

The town provided Libertarian Gary Johnson with his largest percentage of the vote statewide in the 2016 presidential election.

Out of 160 total votes cast in the town, Johnson received 14 (8.75 percent, more than double of his statewide percentage of 4.15).