He attended the Art Institute of Chicago for post-graduate studies, and as a graduate student went to the Écoles d'Art Américaines in the Palace of Fontainebleau in France.

[2][3] In 1934 he and Heath Bowman, whom he had met at Princeton, made a six-month tour of Mexico in a green 1929 Ford Model A convertible.

[6] During World War II, Dickinson served in Naval Intelligence and the Office of Strategic Services in Washington and Italy between 1942 and 1945.

[2] On 29 August 1957 the New York Herald Tribune ran an article titled More than 100 Expatriate Reds in Mexico Viewed as Peril to US.

It said: "Two of Mexico's most picturesque communities - Cuernavaca and San Miguel de Allende - have become the headquarters of some of America's richest and most active communists.

The real leaders of the group, Embassy sources say, are [Albert] Maltz, [Maurice] Halperin, and a so-called 'mystery man' named William Sterling Dickinson...".

Time magazine ran a version of the story titled "Red Haven" in which it said that Dickinson "keeps open house for communists and fellow travellers.

"[8] A Chicago law firm of which Dickinson's father was a partner threatened to sue and obtained public apologies from both journals.

[9] The New York Herald Tribune published an article that praised the institute, the low cost of living and the diversity of the students, making a point of saying "there is nothing Bohemian about the Instituto's group.

He contributed article to the Bulletin of the American Orchid Society[11] In his old age, after retiring from the Instituto Allende, he became involved in a rural library program, continuing to help until his death in a car accident on October 27, 1998, when his van ran off the road and fell over a 50 foot cliff.

[2][3] Dickinson was one of the prime movers in establishing the conditions under which San Miguel revived economically and became a magnet for painters and sculptors as well as retirees from the United States.

Dickinson tried to get his students aware of the Mexican lifestyle and culture through excursions where they encountered the ordinary people of the region in their homes and workplaces, but perhaps did not manage to generate as much interest as he hoped.