Baum settled at the Checkered House after having covered nearly 16 miles in one day. The house served as a shelter for Baum and his officers. At the time, the building was a residence from which he owners had fled. The rebel militia used the Checkered House as a hospital two days after the Battle of Bennington.
At 4 o’clock in the afternoon, we moved our camp into the village near a beautiful house. The house stood empty, the owner had taken to flight with his family this morning.
Julius Wasmus August 13, 1777
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.