The 2024 Pulitzer Prize winning play comes to life on the Playhouse stage
Eboni Booth’s 2024 Pulitzer Prize winning breakout play is an uplifting, gentle and powerful exploration of change, friendship, and quiet courage. Meet Kenneth, a creature of habit whose world is upended when his lifelong job ends – and he’s nudged into the unknown by his best friend Bert and a few unexpected encounters over mai tais at the local tiki bar. This luminous new American play draws us into a deeply human journey, as Kenneth takes small steps into a bigger world – one where every connection holds the power to transform a life.
MEET THE PLAYWRIGHT
MORE INSIGHTS. MORE FUN.
Get more from your experience at the Playhouse by joining us for one of our pre- or post-show events!
Taste of Tuesday 🍽️🍷
Tues, April 14, 2026 at 6PMA fun reception pairing food from a local restaurant partner + wine. Available only as part of our season ticket package.
Buy Package
Together at the Table 🍽️ 🍕
Wed, April 15, 2026 at 5:30PMFor just $15, families / groups can enjoy a communal pizza dinner and casual conversation before attending the performance. Call Box Office at 203.227.4177 to make your reservation.
Pride Night 🌈
Thurs, April 16, 2026 at 6PMA fun, pre-show cocktail party for the LGBTQ+ community and friends! Drinks served by Troupe429 and and appetizers from local restaurants.
Opening Night 🥂
Sat, April 18, 2026 post-showCelebrate the opening of each production along with the cast, crew, and creative team. Free with ticket to the show. Sponsored by RDM Financial Group at Hightower.
Sunday Symposium
Sun, April 19, 2026 post-showJoin us after the show for an exclusive talkback!
Backstage Pass
Wed, April 22, 2026 matinee, post-showLearn how the Playhouse technical staff brought each show to life. No ticket necessary — open to all.
Open Captions
Sun, April 26, 2026 matineeDeaf and hard of hearing audiences can enjoy the performance while watching an easy-to-read digital screen with the actors' dialogue.
Thursday Talkback
Thurs, April 30, 2026, post-showJoin us for a lively Q&A with members of the cast.
MORE
MAKING THEATER OPEN TO ALL.
The Playhouse offers a variety of accessible ticket pricing options, including pay-what-you-will performances, first responder discounts, free tickets for Indigenous peoples, and more.
See ticketing discounts
DINNER & A SHOW
Looking for the perfect pre-show dining spot? Gabriele’s Italian Steakhouse is located on the Playhouse campus and is offering a special $79 menu for Primary Trust ticketholders! Click here to view the menu and pricing, then call Gabriele’s at (203) 454-4922 to make your reservation. Be sure to tell them you are attending Primary Trust to access the exclusive menu and price!
THANK YOU
2026 Programming & Season Sponsorship is generously provided by Barbara Streicker.
Media Sponsorship for the 2026 season is generously provided by Moffly Media and WSHU Public Radio.
OUR 2025/26 SEASON
Six Shows. One Spectacular Season of Theater Throughout the Year.
Something exciting is always in season at the Playhouse! When you visit the Playhouse, there’s always a new story to discover, and a new reason to fall in love with live theatre. Every show offers something completely different—with each one a classic in its own right.
After nearly a century, Westport Country Playhouse continues to evolve—and this season, we’re opening our doors wider than ever before. With celebrated actors, visionary directors, and stunning designs on our historic stage, we’re not just honoring our legacy – we’re writing the next great chapter in our theatre’s history… with you.
Come home to the Playhouse. There’s a red seat waiting for you
Learn more about the season hereMAINSTAGE SUBSCRIPTION
Enjoy the Playhouse and all of our live theater shows with ease today!
A annual subscription that ensures you’ll always have a ticket to to our theater season with benefits including savings, priority, discounts, flexibility, and more! Click below to read about all the perks our Mainstage Subscription has to offer and get yours today!
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