Stand-Up Comedy
In The Grace Note
Join us for a night of stand-up comedy, where the intimacy of the room creates a uniquely close connection for laughter, giggles and guffaws. Headliner Carolyn Castiglia, who has appeared on Comedy Central, MTV, VH1, and more, is a regular on New York stages from Joe’s Pub to The Bell House. Her quick wit and lively, unpredictable style make for a dynamic set that feels right at home in a small space. She’s joined by MothSlam winner Bridget O’Neill, and local favorite Shawn Hollenbach. Hosted by Jenny Rubin. A hilarious night of comedy in Pine Plains!
Bada Swing!
In Banning Hall
Bada Swing! is a lounge-jazz musical comedy that reunites two deeply questionable 1960s crooners, Bobby Bingus and Tommy Linguini, for one last comeback concert. A hit at Joe’s Pub and the New York Comedy Festival, the show mixes live music, oddball storytelling, and sharp humor into a strange, slightly unhinged celebration of ego, nostalgia, and showbiz past its prime.
The Grapes of Laughs SOLD OUT
SOLD OUT!! Pairing Wine with Comedians
Sip, swirl, and giggle at The Grapes of Laughs—a comedy and wine pairing show hosted by Ophira Eisenberg (NPR, The Moth), and featuring Michael Ian Black (Wet Hot American Summer, The State, Stella), hometown favorite Rachel Lenihan, plus Jenny J Rubin (NYC, Egremont Barn). A fantastic lineup of laughs!
Each comic’s set is matched with the perfect wine, blending bold reds, crisp whites, and big laughs for a night that’s part stand-up, part sommelier, all fun. 4 comics, 4 wines, all perfectly paired.
Presented with wine partner Fulton & Forbes Wine & Spirits, Ancram.
Comedy Night 2025
Host Alex Pischera, hometown favorite Rachel Lenihan, and headliner Anthony DeVito bring an unforgettable night of comedy to The Stissing Center. With sharp wit, clever one-liners, and engaging humor, this lineup promises nonstop laughs.