While Wikipedia edit-a-thons may sound like a daunting event opportunity, sharing experiences, guides, and best practices, can make editing an easy engagement opportunity for institutions contributing to Wikimedia Commons through DPLA. Jamie Flood has been organizing and supporting Wikipedia editing events for almost a decade, and has worked the process of organizing an event into an accessible, if not easy, opportunity to engage community members with cultural heritage collections. During the presentation, we will look at different event types/styles, how to handle a work list and tracking, and best practices for outreach to ensure you meet interested community members – and even experienced Wikipedians.