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

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.    

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.

Clifford The Big Red Dog: The Musical is full of extra-large laughs, joy and love - the paw-fect show for Clifford's growing young fans – and nostalgic parents who remember him too.

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.