One of the more difficult 19th-century American texts for high school students to read is undoubtedly Henry David Thoreau's "Walden." His erudite allusions, often page-long sentences, and sophisticated sense of the ironic initially leave many students cold. Still, the author encourages them to read amid the din of a cultural cacophony that shouts "old and outdated" and "tree-hugging dreamer" when confronted with Thoreau's life and work. In this article, the author suggests that rather than relegate Thoreau's writing to the necessary but bitter castor oil of literature, teachers should consider his masterwork to be an ideal vehicle for challenging their complacency amid desperation, a text that crows at teachers repeatedly to wake up. Rather than approach Thoreau with a series of quizzes assessing students' knowledge of allusions and the definition of Transcendentalism, the author offers reading "Walden" as a central axis for the ideas that will develop throughout the year, a baseline for critical inquiry.