Educated as an artist, Stillman subsequently converted to the profession of journalism, working primarily as a war correspondent in Crete and the Balkans, where he served as his own photographer.

Stillman had a contentious relationship with Church but picked up skills in the art of oil on canvas that would serve him well in the small but accomplished group of paintings by his hand that have survived, including, most famously, The Philosopher's Camp (Concord, MA Public Library).

"[1] While Stillman had modest success as a painter and photographer, with far more productivity and innovation in the latter medium, his most lasting contribution to the arts in America was the founding of the periodical The Crayon directly under the influence of Ruskin.

In September 1868 he resigned and went to Athens, where his first wife (a daughter of David Mack of Cambridge), worn out by the excitement of life in Crete, committed suicide.

When the insurrection of 1875 broke out in Herzegovina he went there as a correspondent of The Times, and his letters from the Balkans aroused so much interest that the British government was induced to lend its countenance to Montenegrin aspirations.

[1] He wrote The Cretan Insurrection of 1866–1868 (1874), "The Amateur's Photographic Guide Book" (1874) On the Track of Ulysses (1888), Billy and Hans (1897), "The Old Rome and the New" (1898), The Union of Italy, 1815–1895 (1898), and Francesco Crispi (1899).