Skateboarding has a new face in Gloucester. Looking to put to bed the decades-old stereotype of skaters as punks or grungy teenagers, the Triangle Skateboard Alliance is bringing philanthropy to the next generation of athletes, and president Max Pfannebecker says it’s working.

“Philanthropy is necessary because of the public image of skateboarding,” he said. “The biggest thing you can do to change a stigma is to control the narrative.”

Pfannebecker is one of around a half dozen parents of skaters or former skaters who came together in 2017 to form the TSA, a group dedicated to revitalizing skate parks and building charity into the local skate culture. Pfannebecker’s 10-year-old son is a skater and his attraction to “board sports” helped to kickstart the growth of this mission.

TSA’s model relies on community education grants, contests, donors, and e-commerce from merchandise to raise money to host skate camps and build, expand, a...