The field of computer science has long been plagued by issues of diversity - in particular, attracting and retaining those historically marginalized in computing contexts. This is a great loss to the field, to the future of innovation, and to society. Perhaps most importantly, it is an incalculable loss to those populations excluded from pursuing a passion for computing in the first place. This dissertation chronicles a collection of projects aimed at broadening perceptions of computing, who is participating in computing, and what kinds of artifacts are created with computing. These projects leverage extensive fieldwork in the educational domains of computational craft and open source contribution; they entail (1) course design at the college level and (2) tool and curriculum design for a more open-ended audience of hobbyists and educators. The contribution of this dissertation is documentation of these design processes, along with my subsequent reflections, recommendations, and analysis. First, I share my experience designing two courses developed while on faculty at Berea College: "Craft of Computing", which aims to attract a diversity of first- and second-year students to computing, and "Open Source Software Engineering", which seeks to retain a diversity of upperclassmen through graduation and into computing careers beyond. Second, I revisit my own prior work in e-textiles tool/curriculum design, sharing long-term impact analysis for the LilyTiny sewable microcontroller and accompanying workshop guide. Evidence so far suggests that my forays into college course design successfully piqued students' interest in new domains, while positively influencing their confidence, identity, and sense of belonging. Analysis of the LilyTiny and accompanying workshop curriculum is also promising; it shows that an inexpensive and stable tool, coupled with freely available instructional resources, can indeed achieve widespread adoption in a market suggestive of novice and educational use. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]