Many educators consider the final year of high school to be a "vast wasteland," an epidemic of disengagement. Although high schools across the country have struggled with senioritis, their approaches to the problem have largely fallen into one of three types of responses: vertical acceleration; remediation; and structured containment. New Trier High School in Winnetka, Illinois has recognized the need to engage seniors constructively and, more important, to prepare them for the world beyond high school, whether that is college of the workplace. In this article, the authors discuss the four initiatives adopted by New Trier High School to create a dynamic senior year experience. These initiatives include: (1) a student-driven guidance program that culminates with a day-long senior institute; (2) a powerful classroom mentoring model; (3) a five-week experiential education opportunity that takes place during the final quarter of the senior year; and (4) a yearlong service learning project with Habitat for Humanity.