Understanding the dynamics of mental health among undergraduate students across the college years is of critical importance, particularly during a global pandemic. In our study, we track two cohorts of first-year students at Dartmouth College for four years, both on and off campus, creating the longest longitudinal mobile sensing study to date. Using passive sensor data, surveys, and interviews, we capture changing behaviors before, during, and after the COVID-19 pandemic subsides. Our findings reveal the pandemic's impact on students' mental health, gender based behavioral differences, impact of changing living conditions and evidence of persistent behavioral patterns as the pandemic subsides. We observe that while some behaviors return to normal, others remain elevated. Tracking over 200 undergraduate students from high school to graduation, our study provides invaluable insights into changing behaviors, resilience and mental health in college life. Conducting a long-term study with frequent phone OS updates poses significant challenges for mobile sensing apps, data completeness and compliance. Our results offer new insights for Human-Computer Interaction researchers, educators and administrators regarding college life pressures. We also detail the public release of the de-identified College Experience Study dataset used in this paper and discuss a number of open research questions that could be studied using the public dataset.