This chapter focuses on the design of two critical dimensions of connected making; that is how people can develop maker activities that not only foster connections between makers but also enhance their learning, and how people can support communities of makers in local contexts through global connections. It presents a design-based approach to educational maker activities and communities with an emphasis on fostering connections. The design of the stitch card and the digital mural projects illustrated how maker activities can be tailored to be both accessible and feasible within short periods of time and within public settings. The Connected Hoodies project led participants into crafting and coding more complex electronic textile wearables while still keeping personal designs. The connections and personalizations were intentional, by design, and showcase that educational maker activities can be designed within the DIY spirit by being welcoming to newcomers and by promoting key concepts and practices relevant to STEM activities.