Cutler found inspiration for the majority of his work among the woods and rugged shores of mid-coast Maine. A firm believer in the emotive possibilities of color, Cutler utilized vibrant colors and animated brushstrokes to bring his paintings to life. In Trees and Boulders, he depicts the boulder face in bright pinks, blues, and purples, capturing the light and shadows of the rock in distinctly modern colors.

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Cutler was best known for his participation in two important groups. He first became a member of the “Boston Five,” with modernists Charles Hopkinson, Charles Hovey Pepper, Marion Monks Chase, and Harley Perkins, who collectively sent works to the famous Armory Show of 1913. Later, Cutler and the others were joined by John Goss, and they called themselves the “Group of Six.” Both groups received their share of critical outrage for challenging the well-entrenched conservative painting styles of the day. Today examples can be found in institutions such as the Museum of Fine Arts, Boston, and the Farnsworth Art Museum in Rockland, Maine.