The paper focuses on a unique experiment in education that was realized in Black Mountain College (North Carolina) in 1933–1957 and seeks to find answers to a number of questions. What connects the notions of democracy, education, and the arts? To what extent is Dewey’s version of pragmatism, known as instrumentalism, applicable to education in the arts? And finally, what makes Black Mountain College a revolutionary experiment in education, the importance and memory of which considerably outlasts its less than a quarter of a century existence?