Bay Street Theater Summer 2022: MainStage & Comedy Galore

Mike Birbiglia is performing at Bay Street Theater in the Hamptons
Mike Birbiglia is performing at Bay Street Theater Courtesy Bay Street Theater

One of the highlights of the Sag Harbor summer is Bay Street Theater’s MainStage season. And now that the arts center is back in full force, they’ve got an exciting MainStage lineup and lots more scheduled for the coming sunny months.

The MainStage season kicks off with Windfall May 31 through June 19. In this Scooter Pietsch comedy, five office workers in Columbus, Ohio toil under the heavy hand of a maniacal boss and dream of a better life. When the boss’s antics become too much to bear, they bet their every last cent on a one billion dollar lottery jackpot. But the prospect of winning brings out the worst in these best friends. A dark, hilarious comedy that delves into how far any of us would go in our desire to have it all and live the American Dream. Windfall is produced by special arrangement with John Yonover and Ken Davenport, and directed by Jason Alexander. A MainStage 2022 subscription is the best way to guarantee the best seats to Windfall and the two following MainStage shows.

Arianna Rosario and the "Evita" ensemble at Bay Street Theater, Photo: Lenny Stucker
Arianna Rosario and the “Evita” ensemble, Photo: Lenny Stucker

Nilo Cruz’s Pulitzer Prize-winning play, Anna in the Tropics, comes to Bay Street June 28 through July 24, directed by Marcos Santana. It focuses on a sultry and steamy cigar factory in 1929 Tampa, Florida, where the lives of a Cuban-American family are challenged by the vices and temptations that surround them. The factory owner, Santiago, wrestles with a gambling addiction that’s emboldened by his half-brother, while his daughters, unhappy in their respective relationships, long for the affection of the factory’s handsome lector. Romance, lust and jealousy collide as the family confronts the discontent in their lives, as a wave of modernization threatens to dispel the very traditions they hold dear.

Last of the three MainStage 2022 shows, Ragtime is the epic musical adaptation of E.L. Doctorow’s classic novel that captures the American experience at the turn of the 20th century. The worlds of a wealthy white couple, a Jewish immigrant father and his daughter, and an African American ragtime musician intertwine in this sweeping musical about America’s Golden Age when our nation was mixing, boiling and changing. Ragtime — which features music by Stephen Flaherty, lyrics by Lynn Ahrens and book by Terrance McNally — runs August 2–28. Will Pomerantz, Bay Street’s associate artistic director, will bring together the team with which he created Bay Street’s extraordinary production of Evita to create a visionary new production of this Tony Award-winning contemporary classic to the East End.

Standup at Bay Street

In addition to world-class productions, Bay Street is also home to excellent comedy acts, and the 2022 roster is nothing to shake a watermelon hammer at. Paula Poundstone hits the stage on May 28, Colin Quinn on June 25, Mike Birbiglia July 11–16 (included in MainStage subscriptions) and Preacher Lawson on July 30.

Bay Street Theater is located at 1 Bay Street, Sag Harbor. For ticket sale dates, MainStage subscriptions and more information, visit

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