The purpose of this pilot study is to identify how Waldorf-inspired imaginative teaching methods, and low-technology prototyping promote New Media Literacies (NMLs) development at upper elementary school students. Particularly, the aim is twofold: firstly, to test the feasibility of the research design and validate the research instruments; secondly, to explore the relationship among Waldorf-inspired teaching methods, low-technology prototyping and NMLs development. The study was conducted following mixed methods-grounded theory (MM-GT) methodology by collecting, analyzing, and interpreting qualitative and quantitative data from 104 participants. Specific learning trajectories are traced facilitating students to develop NMLs. Waldorf-inspired hyper-imaginative learning trajectories are unfolded within a six-phases learning process, as particularly effective at low-technology learning environments. Further research should be carried out to gain more insight into the cross-curricular infusion and acquisition of NMLs through Waldorf education across different educational grades.