Learning is most effective when intrinsically motivated through personal interest, and situated in a supportive socio-cultural context. This paper reports on findings from a study that explored implications for design of interactive learning environments through 18 months of ethnographic observations of people's interactions at "Hack The Evening" (HTE). HTE is a meetup group initiated at the State Library of Queensland in Brisbane, Australia, and dedicated to provide visitors with opportunities for connected learning in relation to hacking, making and do-it-yourself technology. The results provide insights into factors that contributed to HTE as a social, interactive and participatory environment for learning--knowledge is created and co-created through "uncoordinated interactions" among participants that come from a "diversity" of backgrounds, skills and areas of expertise. The insights also reveal challenges and barriers that the HTE group faced in regards to connected learning. Four dimensions of design opportunities are presented to overcome those challenges and barriers towards improving connected learning in library buildings and other free-choice-learning environments that seek to embody a more interactive and participatory culture among their users. The insights are relevant for librarians as well as designers, managers and decision-makers of other interactive and free-choice-learning environments.