Rock Point School’s Wiffle Fest returns as joyful fundraiser in June 2026

Rock Point School will bring Wiffle Fest back on June 27, 2026, turning its Rock Point School campus into a 9 a.m. to 5 p.m. showcase for a 28th annual 2-on-2 wiffle ball tournament. The school is pitching it as a joyful fundraiser, and the formula has stayed simple enough to last: friendly competition, local business support and money that goes directly to students and the lives the school says it helps transform.

The event’s staying power is the story. Rock Point School says Wiffle Fest celebrated its 25th anniversary in 2023, which points back to a start in 1998, and the rules page makes plain that this is more than a weekend pastime. It is a scholarship fundraiser built around sportsmanship above all else. A potluck lunch and a field open to players of all ages, as described in a Seven Days listing, fit the same mold: the day is designed to pull alumni, families and neighbors into the same orbit, not split them into spectators and insiders.

The numbers show how much the event has matured without losing its draw. Rock Point School said the 2025 Wiffle Fest raised $27,599 and drew 44 teams, with alumni joining the fun. A year earlier, the school noted its first-ever weather delay, a small detail that says plenty about how established the gathering has become. By 2021, after the previous year was canceled, the 23rd annual event still brought in 32 teams. In 2022, the 25th annual Wiffle Fest grew to 46 teams and was described as the event’s most successful fundraising effort at that point.

That arc explains why Wiffle Fest feels less like a novelty and more like an institution. The school, a coed independent boarding and day school for grades 9-12 in Burlington, Vermont, has built a recurring summer date that alumni recognize, teams return to, and sponsors can rally around. Registration is set at $50 per team, and Rock Point School is also seeking sponsors and donations. The tournament’s longevity is the headline: nearly three decades in, the event still runs on the same mix of bats, flies and belonging that made it work in the first place.