Over the past several years, the bicycle movement in Indianapolis has gained a great deal of momentum. Seventy-four miles of bicycle lanes and trails have been designed and implemented to support travel by bike. Despite the extensive investment in fostering a culture of cycling in the city, there is not yet a significant formal mechanism for documenting and analyzing the effects of these changes. In the case of the city’s bicycling community, records are being created in comments sections of blogs and online newspaper articles, and include personal snapshots and reflections published via social media platforms that are of a troublingly ephemeral nature. The residents of Indianapolis are divided in their estimations of the movement. There has been much debate and sides taken. Like parks, the streets of a community are shared public spaces whose use needs to be negotiated. The bicycle movement in Indianapolis presents an ideal issue around which to develop a digital community archive, as the geographic and mobile nature of the phenomenon will expose the challenges of capturing both place-bound and digital history as it is happening. Information regarding the movement is current and thus is mostly in a digital form. Much like changes to the physical landscape of a city, current digital information can be difficult to grasp all at once as it is widely-distributed.This paper will explore the legal issues related to the collection, organization, and preservation of relevant content that is available through the web, sometimes freely and sometimes behind pay walls. A comprehensive list of potential sources (e.g. newspapers, social media sites, blogs) needed to create an archive with the cycling community will be analyzed to identify the types of legal challenges (e.g. privacy, publicity rights, copyright licensing) would likely face. Recommendations for dealing with these challenges will be made.