When Baum and his officers spent the night on August 13, 1777, the building now known as the Checkered House was a residence, from which the owners had fled. A generation after the American Revolution this road was part of the Northern Turnpike, connecting Troy to Cambridge and points north, opening the eastern portion of Washington County to new markets. New owners operated the house as an inn on the Turnpike and decorated it with a checkerboard pattern. Checkers was a popular entertainment at the time, making it not only a distinctive landmark, but a bit of a marketing ploy.
The Checkered House burned down in 1907, but the landmark lives on through the work of world-famous folk artist Grandma Moses. She painted a number of versions of "Checkered House," in both winter and summer. When asked how she managed to come up with a new composition each time, she said she imagined the scene as if she were looking at it through a window.