[4] Indeed, in the 19th century, humorists attributed the invention of the one-legged milking stool to Pittsfield, "...as a means of conquering a stern difficulty.

"[5] The Farmhouse pictured in this 1915 Postcard to the left still stands and was converted in 1960 to The Fleur De Lis Lodge, for travelers and skiers to stay.

Pittfield was one of thirteen Vermont towns isolated by flooding caused by Tropical Storm Irene in 2011.

[6] According to the United States Census Bureau, the town has a total area of 20.0 square miles (52 km2), all land.

In August 2011, Pittsfield became known as one of the most isolated Vermont towns when Tropical Storm Irene destroyed parts of Vermont Route 100 between Killington and Bethel, preventing vehicle travel in and out of the town for weeks.

The Giorgetti Covered Bridge was completely destroyed by flood waters, along with 8 homes.