About Us

The City School originated in 1987 from some simple questions: "Why are some people homeless? Why don't we learn about it in school? What can we do about it?" Those questions from students at Milton Academy helped launch 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. At The City School, the Youth Outreach Weekend program continues 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.

From those early beginnings, 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 long-term leadership skills of diverse young people concerned with social justice.

Embracing Diversity

Youth at The City School celebrate their diversity and backgrounds, and build relationships across race, class, gender and geography to create caring, learning communities committed to making positive change. City School teens come from Dorchester, Roxbury, Jamaica Plain and Boston's other diverse neighborhoods as well as from suburbs and outlying communities including Ayer, Brookline, Canton, Cambridge, Milton, Newton, Needham, and more.