Last week, New Canaan once again did what it does best: it gathered, it laughed, and it honored one of its own. This time, the spotlight fell on Wendy Hilboldt—a civic stalwart whose contributions to our town are as deep as they are wide. But while the honoree may change each year, the meaning of the Gridiron Club tradition remains constant. It is, in many ways, the annual beating heart of our community spirit.
For those unfamiliar (and we suspect they’re either new to town or overdue for a ticket), the Gridiron Club of New Canaan is not about football. It’s about gratitude. Since its founding in 1961 by State Senator Bob Bliss and Broadway producer Paul Killiam, the club has honored service through an unlikely vehicle: musical theater. Every year, an all-volunteer, all-male cast stages a one-night-only original production gently roasting a beloved community member, chosen by past honorees.
Yes, it’s as hilarious as it sounds. And yes, it’s also as sincere as any tribute ever given under chandeliers or church steeples. The humor is the wrapper, but the gift inside is thanks. In a town rich with committees and contributions, the Gridiron’s genius is that it elevates service not with solemnity but with song. It honors not just what someone has done—but how they’ve done it, and how they’ve made us feel.
That’s what made last week special, as it is every year. Because while the show is rewritten annually and the music changes with the times, the real performance is communal. Neighbors show up not only to laugh, but to bear witness to a life well lived in service to others. It’s our local version of a laurel wreath—minus the toga, plus a few musical numbers.
This tradition—now over six decades strong—is not a relic. It is alive, relevant, and perhaps more vital than ever in a world increasingly suspicious of sincerity. Gridiron reminds us that there is joy in appreciation, and even more in coming together to express it. The producers, directors, and cast are all volunteers. So are the writers, the set builders, the chorus members, and the gentleman who somehow gets roped into playing a third-grade version of the honoree. The entire thing is powered by affection.
And beyond the laughs and the lyrics, the Gridiron also gives back. Since becoming a 501(c)(3) nonprofit in the 1990s, net proceeds from each year’s show have gone to a charity selected by the honoree. That means every punchline and pratfall supports the very kind of selfless spirit the event honors.
We are proud of this tradition—not as spectators, but as participants. Everyone in New Canaan has a Gridiron memory: a spouse in the cast, a parent honored, a line in the show that made us laugh too hard. And all of us know someone who fits the mold of honoree: that rare individual who gives without seeking credit and who now, once a year, receives the loudest possible thank you—in harmony, no less.
Wendy Hilboldt now joins a line of educators, doctors, grocers, artists, town officials, and quiet heroes whose lives have shaped our town and whose stories now echo, comically and lovingly, across the stage. To her, we add our applause. To the Gridiron Club, we offer thanks.
In New Canaan, service matters. And the Gridiron reminds us: so does celebrating it.
