The Nantucket Comedy Festival returns July 8 through July 11 for a milestone 20th Anniversary celebration featuring nationally recognized comedians, signature festival traditions, and unforgettable moments that have kept audiences laughing for two decades.
Festivities begin this Wednesday, July 8, with the free ACK vs. MVY Kids Comedy SmACKdown. As part of the festival’s Stand Up & Learn™ program, student comedians from Nantucket and Martha’s Vineyard will take to the Dreamland Theater stage to perform original stand-up routines, after working alongside professional comedians and mentors. This year marks an exciting first as students from Martha’s Vineyard join Nantucket’s young comics for a friendly island-vsisland showcase of talent, creativity, and humor.
The Comedy Fest officially kicks off Thursday, July 9, at the Nantucket Performing Arts Center with the Roaring 20s Opening Party at 6 pm. For the first time, the pre-party is open to all ticket holders, who are encouraged to don their best Roaring 20s attire for an evening of celebration before Women’s Night of Comedy at 7 pm. This show features nationally acclaimed comedians Judy Gold, Katie Hannigan, and Teresa DeGaetano. This high-energy evening of comedy is a longstanding festival favorite and the perfect kickoff to anniversary weekend.
On Friday, July 10, audiences can enjoy a special screening of Townie at 3 pm in the Dreamland Theater, followed by an exclusive live Q&A with star Steve Sweeney and Academy Award-winning director Peter Farrelly. The acclaimed duo will share behind-the-scenes stories and insights from the making of the film and their careers in entertainment.
Friday evening continues at the Nantucket Performing Arts Center with NCF’s Legends of Comedy at 6 pm, featuring festival favorites Steve Sweeney, Jackie Flynn, Jimmy Dunn, and Tom Cotter. This one-night-only anniversary event celebrates the comedians who have helped shape the Nantucket Comedy Festival and kept audiences laughing year after year.
The 2026 Comedy Festival concludes Saturday, July 11, with the fan-favorite Boston vs. New York SmACKdown at 7 pm in the 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.
As it celebrates its 20th anniversary, the Nantucket Comedy Festival remains dedicated to bringing world-class comedy to Nantucket while supporting its yearround Stand Up & Learn™ educational initiative.
Nantucket Comedy Festival events often sell out, so secure your tickets today. Guests can purchase individual event tickets or upgrade to a Patron Pass for access to all Festival events and exclusive experiences. For details and tickets, visit NantucketComedy.com/attend
