This paper describes an effort to develop a survey measure of adolescents’ interest-related pursuits. The measure focuses on youths’ experiences of connected learning (Ito et al. 2013), an emerging model of learning supported by digital media. The survey measure includes items and scales intended to measure the depth with which youth are able to engage in an interest-related pursuit, the level of support and encouragement they receive from peers, and the degree to which their pursuit involves performance or media production as an essential feature. The survey items and scales also focus on connections between youths’ interest-related pursuits and academic goals, the involvement of adults as co-participants in pursuits, and youths’ access to technology tools they deem necessary for their pursuits. The paper reports on results from a pilot study and field test of these items, in which we estimated the reliability of scales and compared survey results to evidence from interviews with youth. In developing this analysis, our aim was to investigate the feasibility of an approach to measuring youths’ interest-related pursuits to inform future research and evaluation of initiatives focused on digital media and learning.