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White Gradient


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 homelessness and other issues they cared about. 

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 SchoolBoston 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.


The City School develops and strengthens youth to become effective leaders for social justice.

We work with young people ages 14-19 living in Boston and its surrounding suburbs who are emerging leaders and have a passion for social justice. Our community intentionally crosses lines of race, class, gender, and neighborhood.

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Commitment to Racial Justice

The City School believes that change comes from deep commitment to those most impacted by systems of racism and oppression, specifically young people who identify as Black, Indigenous, Latinx, Asian, Arab and/or people of color. The City School is also committed to supporting young people to build relationships across lines of race, class and geography to create caring political homes for youth to organize for change. City School’s youth come from Dorchester, Roxbury, Jamaica Plain and other neighborhoods of Boston, alongside youth from suburbs and outlying communities such as Brookline, Cambridge, Milton, Newton, Needham and more.

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