The Trolley Problem as defined in this paper is a series, or continuation, of increasingly difficult ethical riddles successfully implemented in a classroom environment to spur complex, critical thinking and dialogue. The activity is designed upon the scenario of a runaway train with different and challenging choices, segueing neatly into group discussions of ethics while limiting potential disruptions or controversies. It fits nicely with multiple standards, goals and/or outcomes and can be accommodated to multiple grade levels and courses. It is a powerful, yet easily implemented classroom exercise for educators to develop higher order thinking and dialogue for their students.