The Playhouse's 2026–2027 theatre season is an exciting lineup filled with a vibrant balance of comedy, drama, and plenty of heart.

In 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 addiction. Characterized as a “vividly, beautifully, and painfully described experience,” the author takes his audience on his family’s journey through struggle, grief, and ultimately, healing.  

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.

Join us for our September Script in Hand playreading: The Next Best Thing! Jo is outspoken, inappropriate, and, at 80, a hoot and a half. When her AI programmer son secretly filters her personality into a kinder, gentler version of herself, the resulting android charms her family and granddaughter into preferring her, sparking a Battle of the Ages as Jo fights to oust her synthetic usurper and save her granddaughter from a childhood free of the character-shaping conflict she believes she’ll need to face the world.    

How many times can you tell the same story before it starts telling yours? Featuring beloved songs from the score, behind-the-scenes stories from all three productions, and music inspired by Fiddler's unforgettable characters—including songs that never made it to Broadway—My Year in Anatevka traces one artist's unexpected journey through a musical that suddenly felt less like history and more like a mirror.