The purpose of this chapter is to bring a rigorous and well-studied theoretical framework of motivation to the study and design of virtual learning environments. The authors outline the key motivation constructs that compose Eccles and Wigfield’s Expectancy-Value Theory (e.g., Eccles, et al., 1989; Wigfield & Eccles, 1992, 2000), and how it can be used in the creation of a virtual learning environment designed to promote students’ interest in and motivation to pursue Science, Technology, Engineering, and Mathematics (STEM) careers. In addition, using Brophy’s (1999) model of the motivated learner, the authors outline how this type of motivational virtual environment can be incorporated in classroom instruction to further bolster adolescents’ motivation and competence in mathematics. Finally, they describe a NSF-funded project underway at Harvard’s Graduate School of Education that seeks to develop a 4-day mathematics intervention, merging innovative technologies with regular classroom instruction to spark students’ interest in STEM careers.