A comedy about a struggling actor who turns his NYC rent-controlled apartment into a lucrative AirBNB scheme in this wild-but-TRUE one-man show. Watch Evan Zes portray 25 characters as they close in on him and threaten to ruin his life in this cautionary tale of greed and redemption.

For over 50 years, Ailey II – The Next Generation of Dance – has merged the spirit and energy of the country’s finest early-career dance talent with the passion and creative vision of today’s most outstanding and emerging choreographers. Founded by Alvin Ailey in 1974, this universally renowned company embodies his pioneering mission to establish […]

Westport Country Playhouse will present a masterclass with actor Andrew Keenan-Bolger, best known for originating the role of Crutchie in Disney’s “Newsies” on Broadway. Titled “Building Characters from the Inside Out,” the interactive masterclass will give participants an opportunity to explore the craft of character development through monologue work, script analysis, and imaginative storytelling. The […]

Featuring beloved songs from the score of Fiddler on the Roof, behind-the-scenes stories, and music inspired by Fiddler‘s unforgettable characters—including songs that never made it to Broadway—My Year in Anatevka […]

Westport Country Playhouse will present a Script in Hand playreading on Monday, September 14, at 7 p.m., of “The Next Best Thing,” a new comedy about an outspoken, wildly inappropriate […]

Come together and sing along – with a little help from your friends – for one unforgettable night of Beatles music at Westport Country Playhouse! Music Director Drew Wutke leads a powerhouse live band and an extraordinary lineup of Playhouse favorites and special guest performers in a celebration of the songs that changed the world. […]

n The History of a Brief Time, written and performed by Bill Williams, the author and activist tells the very personal story of the loss of his son, William, to opioid […]

Enjoy an unforgettable evening with Master Illusionist Michael Grandinetti, star of NBC’s “The World’s Greatest Magic”, The CW’s “Masters of Illusion”, and POP’s “Don’t Blink”, airing in over 100 countries […]

Shake off the end of summer and kick off a brand-new season at the Playhouse with CRUEL SUMMER – an electrifying night celebrating the biggest voices in pop! Featuring the music of Ariana Grande, Olivia Dean, Taylor Swift, Sabrina Carpenter and more! This high-energy concert features a rockin’ live band with a lineup of powerhouse […]

Westport Country Playhouse Family Festivities Series presents Saturday, August 22, 2026 at 4PM Silly Dilly Songs Written by Alan Katz Recommended Ages: 2-8 year olds