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Vinegar Hill Music Theatre presents a NY VS Boston Comedy Show!
Food Trucks 6pm Doors 7pm | Show 8pm
All Ages


Join us for food and drinks before the show in our outdoor garden starting at 6pm!

The night’s food truck is Stone & Fire Pizza – serving up classic and original hand-tossed, wood fired pies like Rosemary Apricot, Margherita, and Loaded Potato!



New York vs. Boston Comedy Series:

The rivalry between New York and Boston is timeless and extends beyond sports, politics, and bootlegging; it also includes comedy. The New York versus Boston Comedy Series began in Nantucket and later moved to Bridge Street Live before arriving at Vinegar Hill. This event premiered in 2010 and has been taking place annually ever since. During the event, comedians from both cities showcase their unique style and wit on stage in a humorous face-off. The show features talented comedians from each city and has been a hit with audiences. The battle between New York and Boston comedians continues to entertain audiences, whether it’s on stage, screen, or social media. If you’re looking for a playful and entertaining experience, be sure to check out the show.


Hosted by Mark Riccadonna

Mark Riccadonna is a talented comedian, actor, and writer. He studied theater at The American Academy of Dramatic Arts before discovering Stand-Up Comedy. Mark is a successful storyteller, entertaining audiences worldwide, including US and UN troops. He has acted in several films, including the lead role in “Days of Power”. Mark is also a columnist and author, co-authoring “The Two Guys Two Way Joke Book”. His podcast, “Drinks Jokes and Storytelling,” showcases his wit and storytelling abilities. Coming fresh off his Dry Bar Special Domestic Nomad.


Team Boston: Tony V

Meet Tony V, a talented comedian who began his stand-up career in 1982 at Boston’s Comedy Connection. He quickly rose to headliner status and was named the “Funniest Person in Massachusetts” in 1986. Tony V has made numerous television appearances and acted alongside notable actors such as Eric Roberts and Ice T. He’s also appeared in several films and has performed for charitable organizations. Tony V has shared the stage with comedy legends and musical acts alike, making him a well-rounded performer.


Team NY: Kevin Flynn

Kevin Flynn is a versatile talent who has made a name for himself in various fields. He began his career as a professional soccer player before transitioning into comedy. Since then, he has made numerous television and film appearances as both a comedian and an actor. Apart from comedy, Kevin has excelled in other areas, such as acting, sports hosting, and adventure shows. He has also created one-man shows and is the Founder and Executive Director of the Nantucket Comedy Festival. Kevin’s contributions to both the entertainment world and youth education are commendable!


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