The
Old Charlestown Schoolboy's
Association

The Old Charlestown Schoolboys Association, often referred to as the Old Schoolboys, stands as the oldest educational organization in Boston's historic Charlestown neighborhood, with roots tracing back over a century. Established initially as a temporary group to organize a reunion for former students of Charlestown's primary, grammar, and high schools prior to the area's annexation to Boston in 1874, the association held its inaugural gathering on June 13, 1914, at the Monument grounds, drawing around 500 attendees to reminisce and foster lasting connections. What began as a one-time event evolved into a enduring institution, marked by annual reunions—reaching its 112th in 2025—that celebrate camaraderie and the shared heritage of Charlestown's school alumni.

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At its core, the association promotes brotherly love through dedicated community service, having provided scholarships and educational assistance to young men in Charlestown for 113 consecutive years as of 2026. This support has empowered generations, with many beneficiaries going on to become active members themselves, perpetuating a cycle of giving back. Beyond scholarships, the organization contributes to local charities, bolstering community initiatives and receiving recognition such as grants from the Charlestown Community Impact Fund.

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Through these efforts, the Old Charlestown Schoolboys Association continues to honor its founding spirit while making meaningful impacts on education and welfare in one of Boston's most storied communities