Bay Street Theater announces its 2022 Summer Season

Bay Street Theater's 2018 mainstage production of "Evita." Photo by Lenny Stucker/Courtesy Bay Street Theater.

Bay Street Theater in Sag Harbor has announced its schedule for the 2022 Summer Mainstage Season. The three productions will be “Windfall” (May 31–June 19), a new comedy by Scooter Pietsch, directed by Jason Alexander; “Anna in the Tropics” (June 28–July 24) the Pulitzer Prize-winning play by Nilo Cruz, directed by Marcos Santana; and “Ragtime” (August 2–28), with music by Stephen Flaherty, lyrics by Lynn Ahrens, and a book by Terrence McNally, directed by Will Pomerantz.

Jason Alexander will direct the Bay Street Theater production of “Windfall,” a new comedy by Scooter Pietsch. The play will run May 31 to June 19. Courtesy Bay Street Theater.

In the comedy “Windfall,” five office workers in Columbus, Ohio toll 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. Directed by Jason Alexander.

Marcos Santana will direct “Anna in the Tropics,” the Pulitzer Prize-winning play by Nilo Cruz, at Bay Street Theater. The play will run June 28 to July 24. Courtesy Bay Street Theater.

Nilo Cruz’s Pulitzer Prize-winning play, “Anna in the Tropics,” centers 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. Directed by Marcos Santana, whose work has been seen at Bay Street as choreographer of “Evita” and “Camelot.”

Bay Street’s production of “Ragtime” (August 2–28), with music by Stephen Flaherty, lyrics by Lynn Ahrens, and a book by Terrence McNally, will be directed by Will Pomerantz. Courtesy Bay Street Theater.

Rediscover America with “Ragtime,” 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. Will Pomerantz, Bay Street Theater’s associate artistic director, will bring together the team with which he created Bay Street’s production of “Evita” to create a visionary new production of this Tony Award-winning contemporary classic to the East End.

Full cast and creative teams will be announced soon. Subscriptions are available by calling the Box Office at 631-725-9500 or online at