Thomas Hart Benton first traveled to Martha’s Vineyard in 1920, far ahead of the crowds that eventually transformed it into a popular vacation destination. The region had a profound impact on the artist, prompting him to later purchase a cottage in the town of Chilmark. The high horizon line in Chilmark Landscape (1925) testifies to Thomas Hart Benton’s unusual artistic practice. In preparation for his paintings, Benton first created clay models for various elements of a scene, which he laid out to form a three-dimensional rendering. He experimented with color by painting the models, and when settled on the final composition, he then painted the scene on canvas or panel. In Chilmark Landscape, the undulating hillside imbues the scene with a raw energy that evokes the untouched landscape of Martha’s Vineyard in the 1920s. Benton painted approximately 200 Martha's Vineyard scenes, and approximately 40 examples of Chilmark.