Little began exhibiting at the Boston Art Club in 1881, submitting works done in watercolor and oil with titles such as Outward Bound, The Song of the Sea, and Marine, that demonstrated his predilection for coastal themes. He married Lucretia Shephard Jackson in 1883 and by 1886 the couple had moved to Salem, where Philip shared studio space with Benson at 2 Chestnut Street. Two years later, the Littles purchased a stately home at 10 Chestnut Street, while Benson established a studio in Boston and took a teaching position at the Museum School, but both artists remained close friends and deeply tied to Salem; the Benson family would eventually purchase 14 Chestnut Street in 1924. Little’s familial wealth allowed him to continue his artistic pursuits and exhibit with the Boston Art Club, while also becoming an integral member of Salem’s civic community. He served in the Massachusetts National Guard between 1887 and 1901, retiring as a Major; represented his ward on the town council in 1891; was elected twice to the Salem Board of Aldermen the next two years; and was a member of the Salem School Board from 1898 until 1912. He was also involved with the Essex Institute (precursor of the Peabody Essex Museum) for decades, eventually serving as curator of art.

Known for his impressionistic oils and watercolors of New England, as well as his etchings and lithographs, Little was proud of his American education and gratified not to have come under the influence of European methods and subject matter: “I am distinctly American in my ideas as regards the future of its art, which I believe should break away from the trammels of the European schools and produce individual living stuff from our own resources.”  His paintings often captured Salem’s waterfront in all seasons, while many others were completed during summers spent at the family home on MacMahan Island, Maine, an environment conducive to the artist’s interest in the effects of light, wind, and climate on his subject matter. His first one-man exhibition at Boston’s Rowlands Gallery in December 1907 lauded this quality of his work: “Weather, in its manifestations of various visible phenomena, is remarkably felt and expressed in some of these landscapes; one is aware of the mood of the elements…Although Mr. Little is wholly absorbed by the aspects of the things he sees, and makes no attempt to philosophize in paint, he does not escape the poetry that is inherent in his vocation; he has had the vision, he has tried to make it his own, and we must recognize the sincerity and success of the endeavor.”  Over the next decade, numerous solo shows eliciting similar praise were held at institutions across the country, including the Worcester Art Museum in 1909, the City Art Museum in St. Louis, Missouri, in 1910 and 1913, the Colorado Springs Art Academy in 1913, and the Portland Society of Art in Maine in October-November 1914. One month later, the recently founded Guild of Boston Artists organized a two-person exhibition of Little’s work, alongside sculptor Cyrus Dallis, in which he included several canvases with a human element, a feature remarked upon by the critic for the Boston Evening Transcript: