This paper explores the philosophical background of one of the most widespread Web based sources used in contemporary education--Wikipedia. Theoretical part consists of the basic notions of anarchist philosophy of education such as human nature, work and society. Through Chomsky's prism of visions and goals, it provides the frame for further analysis. The practical part shows that Wikipedia creates a virtual anarchist society: open, ludic engagement in this society is fully interwoven with the specific kind of education of all its members. Offering an insight into the often neglected area of social and political ideas underlying the use of technology in education, this paper offers a conceptual bridge between contemporary Digital Immigrant educators and their predominantly Digital Native patrons, thus contributing to the better understanding of education in and for the third millennium. (Contains 1 figure.)