What continues to connect the Woodstock generation and the post-risk generations are the threats – political, economic, environmental, epidemic – of an increasingly precarious world. In the wake of plans for a 50th anniversary Woodstock event being abandoned due to the failure of the organizers to secure a site, this article considers the impact of Woodstock’s legacy on contemporary music festivals and whether a 50th anniversary Woodstock event may have sparked a revived interest in the rock festival as a platform for engaging at an ideological level with major issues unfolding in the world during the early twenty-first century.