Don’t miss Comedy & Cabernet at City Winery Boston. A n evening of top-tier stand-up paired with great wine and atmosphere. Headlined by Will Smalley, a dynamic and hilarious voice in today’s comedy scene, the show blends sharp wit with playful absurdity. A former festival finalist and performer at the Bridgetown Comedy Festival, Smalley has become a standout across the Northeast with his bold, charismatic style. Also an announcer at American Repertory Theater Oberon and a featured act at Mysteryland Festival, he brings a fresh, high-energy presence you won’t want to miss.

Maria Palombi

Jim Whitman

Jessie Baade

Will Smalley