Arts and Entertainment
July 14, 2025
From: Westport Country PlayhouseWhat's On THIS WEEK at the Playhouse!
Monday, July 14 at 7PM
Singin' in the Rain (1953) is splashing onto the big screen at The Playhouse — and it's more dazzling than ever! Join us for a timeless cinematic classic packed with toe-tapping tunes, unforgettable romance, and the kind of joy only Gene Kelly can deliver.
General Admission; Seating unreserved
Advertising Partner
The Wein Group/Morgan Stanley
2025/26 Mainstage Season
Single Tickets on Sale
Tuesday, July 15
They're here! Single tickets for our 2025/26 Season are officially on sale!
Get ready for a year full of show-stopping hits, beloved classics, and thrilling new productions. Secure your seats today - and let the countdown to curtain begin!
Three Major Mainstage Productions And Three Shorter “Add-ons”
Learn more & Purchase your tcikest!
Rosanne Cash with John Leventhal
Wednesday, July 16 at 8PM
Enjoy an evening of song by four-time Grammy Award winner and one of the country’s pre-eminent singer-songwriters, Rosanne Cash, with her husband and acclaimed Grammy-winning songwriter and guitarist John Leventhal.
Friday, July 18 at 5PM
Stand up and Learn Performance
Join the students perform their original stand?up routines and collaborative comedy sketches. Students will step into the spotlight with original stand?up routines and collaborative comedy sketches that beautifully blend humor, self?expression, and critical thinking. Drawing on stand?up pedagogy - think joke?writing, timing, performance, and “reading the room” like a pro comedian!
Friday, July 18 & Saturday, July 19 at 10:30AM
FROM THE PAGE TO THE STAGE
Whether you're a longtime theater lover or simply curious about what happens behind the curtain, this guided tour offers a unique peek into our historic Playhouse. Explore the stage, backstage areas, and dressing rooms, and hear stories from nearly a century of theatrical history.
Karma Kabaret
Saturday, July 19 at 8PM
“Where Broadway meets Namaste!”
Karma Kabaret is an entertainment written with the intention of putting goodness into the world: by making people laugh — a lot — and think a lot and discover a lot and feel a lot and laugh — a lot!
Part of the Barnstormer series
Steep Canyon Rangers
Sunday, July 20 at 7PM
The Grammy Award-winning Bluegrass/Americana band
Get ready for an unforgettable night of bluegrass brilliance. Known for their high-energy performances, tight harmonies, and genre-bending sound, this band blends tradition with innovation like no other.
Whether you're a lifelong fan or new to their music, this is your chance to experience the magic of one of America's most acclaimed acoustic bands - live and in person.
ONE MONTH AWAY!
Linedy Genao: Songs From My Sala
Tuesday, August 12 at 7PM
Songs From My Sala invites you into the warmth of Linedy’s Brooklyn sala - her childhood living room - where the rhythms of her Dominican?American heritage and the songs that shaped her dreams come alive. From singing in church to making history on Broadway as the first Latina to originate a lead role in Andrew Lloyd Webber’s Bad Cinderella, Linedy shares stories and music with soulful intimacy. This solo brings together vibrant anthems, heartfelt memories, and a celebration of identity, resilience, and home.
Tickets: $45, $40