[3] After graduating and traveling through parts of Italy, White moved to Chicago and worked for Hull House, a settlement that provided a creative and educational environment for poor residents of the surrounding neighborhoods.

[4] In 1902 White joined forces with Ralph Radcliffe Whitehead (1854–1929) and painter-lithographer Bolton Brown to found the Byrdcliffe Colony in Woodstock, New York, conceived as a utopian community of studios, workshops, and artistic gatherings which would nurture creative freedom in the idyllic setting of the Catskill Mountains.

In 1905, White purchased a farm just outside Woodstock with Fritz van der Loo and Carl Eric Lindin, intended as a rustic haven for the three friends and their families.

[7] White would go on to build the Maverick into a thriving community with makeshift studios, a printing press, and a steady output of publications devoted to literature and the visual arts, most notably The Wild Hawk and The Plowshare.

Revelers were encouraged to come in costume; period photographs include men and women with flowers in their hair, a historical prototype for the popular cliché of the Woodstock hippie.

The festivals were by the 1920s an annual occurrence, in August on the night of the full moon:[9] they lasted until 1931, when their reputation for wildness (numbers of attendees reached, according to some reports, as many as 6000) pressured White to put an end to his tradition.