Adolescents who experience bereavement following suicide are at increased risk for adverse outcomes, including depression. However, there is limited research on the heterogeneity of depressive symptoms or its long-term course among this population. Using a self-reported 3-item version of the Center for Epidemiologic Studies Depression Scale (CES-D) administered across five waves spanning from adolescence to adulthood (1994–2018, with intervals of 1, 5, 7, and 9 years), we identified trajectories of depressive symptoms over a 24-year span in a sample of adolescents (n = 236) who reported at baseline having lost a family member or friend to suicide in the last 12 months. We identified three distinct depressive symptom trajectories: Stable low symptoms (77.5%), initially high but gradually declining symptoms (16.9%), and initially low but gradually increasing symptoms (5.5%). Race, neuroticism, sleep quality, and age were significant predictors that differentiated membership among the three trajectory groups. Implications for developing personalized assessment and intervention are discussed.