Littlefield's artistic journey began with a deep interest in art and classicism during his time at the Roxbury Latin School. He further cultivated his passion at Harvard University, where he studied painting under Adeline Wolever, known for her traditional Boston School style influenced by artists like Frank Benson, Edmund Tarbell, and William Paxton. Graduating from Harvard in 1924, Littlefield ventured to Paris to advance his painting studies. Returning to the U.S. in 1929, he settled initially in Boston and later spent summers on his family's property in Falmouth, Massachusetts on Cape Cod, where he explored landscape painting and gained recognition through his early commissions and exhibitions.

Littlefield's career milestones include participation in the Whitney Museum's First Biennial in 1932, a group exhibition at the Museum of Modern Art (MOMA) in 1936, and his debut solo exhibition in Boston in 1938. In 1947, he co-founded the Cape Cod Art Association and began exhibiting at the Provincetown Art Association, where he studied under Hans Hofmann and became involved with "The Club," a group of abstractionists in New York City. His later works predominantly embraced abstraction.

Beyond paintings, Littlefield worked across various media, producing pen and ink sketches, portraits, nudes, murals, theater sets, collages, and frames. His artworks are housed in prestigious museums including the Fogg Museum at Harvard, the Museum of Fine Arts Boston, and the Museum of Modern Art in New York. Private collectors of his works included notable figures such as Mrs. John D. Rockefeller, Lincoln Kerstein, and Mrs. Paul Mellon.

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