Celebrating 20 Years of Laughter
The Nantucket Comedy Festival returns July 8–11, 2026, for a milestone 20th Anniversary celebration filled with unforgettable performances, signature events, and community traditions that have defined the Festival for two decades.
The celebration begins Wednesday, July 8 at 3:00 PM with the free ACK vs. MVY Kids Comedy Smackdown! As part of the Nantucket Comedy Festival's Stand Up & Learn program, student comedians from Nantucket and Martha's Vineyard will take the stage to perform original stand-up routines after working with professional comedians and comedy mentors. This year marks an exciting first for the program as we welcome students from Martha's Vineyard to join Nantucket's young comics for a friendly island-to-island showcase of talent, creativity, and humor. Join us for this free event and help cheer on the next generation of comedic talent.
The weekend officially kicks off Thursday, July 9 at the Nantucket Performing Arts Center with the Roaring 20’s Opening Party at 6:00 PM, open to all ticket holders, followed by Women’s Night of Comedy at 7:00 PM. This beloved Festival tradition features Judy Gold, Katie Hannigan, and Teresa DeGaetano for an evening of sharp wit, big laughs, and high-energy performances. Wear your best 20's attire!
On Friday, July 10, the Festival heads to Dreamland Theater for a special screening of Townie at 3:00 PM. Following the film, audiences will enjoy an exclusive live Q&A with star Steve Sweeney and Academy Award-winning director Peter Farrelly, offering behind-the-scenes stories and insights from two iconic figures in comedy.
Friday evening continues at the Nantucket Performing Arts Center with Legends of Comedy at 6:00 PM, featuring Festival favorites Steve Sweeney, Jackie Flynn, Jimmy Dunn, and Tom Cotter. This special anniversary event celebrates the comedians who helped build the Nantucket Comedy Festival and keep audiences laughing year after year.
The Festival concludes Saturday, July 11, with the fan-favorite Boston vs. New York SmACKdown at 7 PM at Dreamland Theater. This signature event features Brian Scott McFadden and Vladimir Caamaño representing New York, facing off against Boston favorites Dan Boulger and Tom Dustin in a fast-paced evening of stand-up, storytelling, and friendly rivalry. Returning to keep the peace is longtime referee Bob Ley, who has officiated the SmACKdown since its inception.
Individual tickets are on sale now at nantucketcomedy.com/attend
Whether you're joining us for a single show or celebrating all weekend long, we can't wait to welcome you for 20 Summers of Laughter!
