Like the Troy fire, the Checkered House was a local legend. Situated along the Cambridge Turnpike, it was an inn where stagecoach drivers had changed horses as far back as the eighteenth century. During the Revolutionary War, the inn served as General Baum's headquarters and field hospital. Its checkerboard front made the house a distinctive landmark that was remembered long after it burned in 1907.
Moses 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. By then shifting her viewpoint slightly, she could cause the elements to fall into place differently.