The City School originated in 1987 from a simple question: "Why are some people homeless, why don't we learn about it in school, and what can we do about it?". That question, from a student at Milton Academy, helped start Youth Outreach Weekends, where adult mentors guided teens on service retreat weekends to help uncover the root causes of homelessness and devise actions they could take on homlessness and other issues they cared about. Youth Outreach Weekends continue to this day.

From that start, the Summer Leadership Program began in 1995 as a way to intentfully continue the learning that many young people received on the weekends. The Summer Leadership Program was a collaboration between Cathedral High School, Boston Latin School, and Milton Academy, bringing together a diverse range of teens for hands-on leadership training, seminars on some of the most pressing issues of the day, and a focus on building community and bridging relationships. Today, the Summer Leadership Program brings together youth from across Boston's diverse neighborhoods and from many suburbs, and has expanded to include internships at local nonprofits for all teen participants, and Community Action Projects where the students develop and implement concrete, meaningful projects throughout the city.

In 2008, The City School has grown into a vibrant center for youth leadership development, offering after-school, weekend and summer programs that focus on critical thinking, community building, service work, reflection and action. Our programs continue to unite high school students from the full range of our society, developing the long-term leadership of diverse young people concerned with social justice.

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