For the last 26 years, social workers, teachers, and staff at a Long Island high school have offered a biannual, intensive 36-hour weekend retreat to provide students with the opportunity to build connections, confront stereotypes, explore social issues, and express emotions. The retreat, called Awareness Weekend, is an occasion for students to “break down walls and build bridges” in a safe space created in their own school building. This program was created by a high school social worker in 1989 and, over the years, has become an important part of the culture of this diverse suburban school. Research shows that abuse, community violence, harassment and bullying, and drug and alcohol use are among the many risk factors teenagers face (Boxer, 2010; Bell & Jenkins, 1993; Kann et al., 2014; Muehlenkamp, 2005). A nationally representative study found that one in five children either currently experience or will experience during their lifetime a debilitating mental health problem (Merikangas et al., 2010), and many of today’s youths do not have appropriate contact with clinical mental health services (Tolan & Dodge, 2005). With a lack of education and access to helping resources, many teenagers resort to negative coping strategies such as substance abuse and self-harm. Fortunately, the school environment can offer some of the supports these students need. Positive prevention programs—interventions focusing on building strengths and resilience among youths to increase the likelihood of healthy outcomes—such as Awareness Weekend can provide a lifeline for struggling teenagers.