The Old Charlestown Schoolboys Assocation gets together one night each year and members of the association attend a reunion. "It Keeps you in touch with all the people you knew, all the people you went to school with, all the people you played ball with, all the people you played against." said George Murphy, a member of the executive committe and past president of the organization. As noted by Bill Morrissey, the 2010 president,"the hallmarks of these reunions are nostalgia and sociability." The Old Charlestown Schoolboy's Association is the only group of its kind in Charlestown and likely the state. Its first incarnation was launched in 1880 to reunite alumni from the Training Field School (later renamed the Winthrop School). The school went out of existence, so there was no future of potential membership. A second Schoolboy’s Association was subsequently formed in 1913, which included past students from all of Charlestown’s public schools. Today, the organization is open to men who are at least 50 years old and have attended any school in the town. In rare instances, honorary members who didn’t attend school in Charlestown are inducted into the organization.,
Though the Schoolboys hold regular meetings throughout the year, their work culminates in the Annual Reunion, a banquet that takes place on the second Thursday in May of each year at which time a wide variety of scholarships are awarded to the current generation of schoolboys.. Members will attend the event and feast on the traditional meal of hot baked chicken pie and banana fritters. Those attending this year made the pilgrimage from locations as far away as Florida and California. Members come from diverse backgrounds ranging from professionals to blue-collar workers. At the banquet, however, all these differences are cast aside, and all the members are once again peers. Recently, a long-absent tradition has been reinstated. It is the ringing of a school bell by the oldest schoolboy present to signal the opening of the annual reunion banquet.
In 2010 at the 97th Annual Reunion, a new tradition was established, the “James W. Conway Community Service Award.”. This award is presented to a citizen of Charlestown who by his exceptional dedication has demonstrated his unswerving devotion to enhancing the quality of life for Charlestown citizens and epitomizes the fundamental principles and core values of the Old Charlestown Schoolboys Association.