City Winery Boston & Boston Comedy Festival Present: Comedy & Cabernet. The best in local comedy and wine! The Boston Comedy Festival has been decanting the best comedy shows in New England for over 20 years. You have seen these comedians on Drybar, HBO, Team Coco, Jimmy Kimmel Live, Comedy Central, and headlining your favorite club or theater.

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.