Westport Country Playhouse: Both Sides Now

The other day, Judy Collins played the Westport Country Playhouse.

In a strong, still-mesmerizing voice, the 84-year-old legend captivated the full house. Her encore — “Amazing Grace” — brought many to tears.

Judy Collins earlier this month, at the Westport Country Playhouse. (Photo/Lynn Untermeyer Miller)

It was an audience, to be sure, of a certain age.

It was the same type of audience that for several years had stayed — or strayed — away from the Playhouse.

Or, if they went to a play there, might have left at intermission. For a while, the historic institution lost touch with its audience.

COVID did not help. Across the country, regional theaters — even those in far bigger markets than Westport — are struggling.

The Westport Country Playhouse, though, has come roaring back.

Westport Country Playhouse. (Photo/Lynn Untermeyer Miller)

After a thisclosetodeath experience last summer, it is once again a thriving, go-to destination.

And it has done it by appealing to a lot more audiences than just the Judy Collins crowd.

In the past 8 months — since a desperate, we-really-may-close plea raised $2 million — the theater that once ran a summer-only schedule, filled with famous names and shows that often headed next to Broadway, has pivoted wisely.

An evening with Justin Paul, Kelli O’Hara and James Naughton launched the reimagined schedule of a wide array of entertainment options. (Plays are now planned for fall and winter only, beginning this October.)

Here’s a (partial) list of what’s drawn large audiences since last fall:

  • Mandy Patinkin
  • Songs of Ella Fitzgerald
  • “The Lightning  Thief”
  • “A Sherlock Carol”
  • “Good Witch/Bad Witch”
  • A salute to Westport volunteers
  • “A Night for Swifties”
  • Audra McDonald
  • Puppet wrestling
  • Westport’s Own Jean Louisa Kelley.

“Dear Evan Hansen,” “La La Land,” “The Greatest Showman” composer — and Staples High School graduate — Justin Paul, at the Playhouse last September. (Photo/Jerri Graham)

Meanwhile, community groups rented the Playhouse for “Rodgers & Hammerstein’s Cinderella,” “Gloves for Good” (boxing!), the world premiere of Triple Threat Academy’s “Presumed Incompetent,” and more.

Still to come, over the next 5 months:

  • “The Life and Times of Ruth Bader Ginsburg”
  • A celebration of Jewish Broadway
  • Bernadette Peters
  • Mike Birbiglia
  • An evening with Tony Kushner; another with Fran Lebowitz
  • The Bacon Brothers
  • Isaac Mizrahi.

All that, in addition to the usual Script in Hand play reading series, and special events like guided tours of the Playhouse (sit in the green room! walk onstage!) on April 26, then twice a month from May through July.

The Westport Country Playhouse is clearly not your grandfather’s theater.

Though your grandfather is happy to be back.

It’s a remarkable turnaround, and one that benefits everyone.

A 90-plus-year tradition that was days away from being lost is now back on secure footing.

Younger audiences — long an after-thought — are discovering a town jewel, hidden in plain sight.

Westport is reclaiming its reputation as an arts community. We’ve always called ourselves that, though we do not always walk the talk.

Soon after it opened in 1931, the Westport Country Playhouse became a summer destination — and a launch pad for Broadway shows.

From a practical point of view too, a rejuvenated Playhouse can only help our merchants and, especially, our restaurants.

Theater-goers who come early may have a chance to explore downtown. For many of them too, dining out is a part of the entire theater experience.

(Perhaps the only person with a bone to pick is the owner of Gabriele’s Steakhouse next door. He can no longer count on folks coming to eat after walking out of a show at intermission. On the other hand, his location makes him the most likely restaurateur to see an uptick in pre-show reservations.)

On June 5, 2023 “06880” broke the story of the Playhouse’s dire straits.

“Now, in its 92nd year, the Westport Country Playhouse is limping through a truncated season,” we said. “It might not make it to 93.”

They needed $2 million to survive.

Less than 2 months later — on August 3 — “06880” reported: “Today, the Playhouse said they’ve collected $1,941,557 in cash and pledges. Donations were based on the board of trustees’ promise to transform the historic theater into ‘a performing arts center that appeals to a broader audience while continuing to produce theater.’”

Over the next few months, they made good on that plan.

I was skeptical. Drastic layoffs made me fear that — despite their love for the institution — the remaining skeleton staff could not pull off such a turn-around.

I was wrong. The high-wire act worked.

And though it’s unlikely a circus will ever take over the storied stage, just about everything else is possible.

The Westport Country Playhouse survived. Its 92nd season was not its last.

Now it’s up to all of us to keep it going for at least 92 more.

(“06880” keeps a close eye on Westport’s arts — past, present and future. Please click here to support our hyper-local journalism. Thank you!)

Creative programming is filling the Playhouse’s historic seats. (Photo/Robert Benson)

4 responses to “Westport Country Playhouse: Both Sides Now

  1. Dorothy, Robertshaw

    Onward and upward we will survive for sure. It’s one of the great attractions about Westport🧑‍🎨👍 and its thriving, cultural arts Community and meeting place . As part of the artist collective of Westport we are so thrilled that they share their generous space with us🧑‍🎨

  2. Priscidlla Hawk

    Having real musical plays, like Cinderella, which in spite of its name was a well known, all ages ,musical, with an orchestra in the pit, would really bring the crowds! Priscilla Hawk

  3. Kudos to the rejuvenated Board of Directors under new and able leadership and the always loyal staff, also under new leadership, for pulling off this amazing turn around. It is a pleasure to have conversations about the Playhouse that are not centered around “doom and gloom” but about the positivity of what has occurred since the restructuring of the Direction and the Management of the Theater.
    Roz and Bud Siegel

  4. It’s been a joy to attend performances by Mandy Patinkin and Audra McDonald and plays like “Dial M..” among others. Many thanks to the Westport Country Playhouse. Please keep doing what you’re doing.

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