Learning music theory not only has practical benefits for musicians to write, perform, understand, and express music better, but also for both non-musicians to improve critical thinking, math analytical skills, and music appreciation. However, current external tools applicable for learning music theory through writing when human instruction is unavailable are either limited in feedback, lacking a written modality, or assuming already strong familiarity of music theory concepts. In this paper, we describe Maestoso, an educational tool for novice learners to learn music theory through sketching practice of quizzed music structures. Maestoso first automatically recognizes students’ sketched input of quizzed concepts, then relies on existing sketch and gesture recognition techniques to automatically recognize the input, and finally generates instructor-emulated feedback. From our evaluations, we demonstrate that Maestoso performs reasonably well on recognizing music structure elements and that novice students can comfortably grasp introductory music theory in a single session.