Ann Sheffer: A True Westport Playhouse Star

In the mid-1960s, Steve Gilbert was a beloved Staples High School art teacher. After school — as technical director for Players — he taught students how to create the remarkable sets that gave that drama troupe some of its early renown.

Each summer, Gilbert had another job: general manager of the Westport Country Playhouse. His Staples connection gave him an easy pipeline to willing workers. He hired set builders, ushers, even parking lot attendants.

Some of Gilbert’s teenagers — like Lindsay Law and Ann Sheffer — went on to careers in theater or TV.

Nearly all recall those summers as defining moments of their lives. They learned so much about the arts. They interacted with stars, and struggling actors. They hung out there together after work, and formed lifelong bonds.

“That’s where we grew up,” Sheffer recalls.

Staples Players received a replica of the Globe Theater. Steve Gilbert is at far left; Ann Sheffer is on the far right.

On Saturday, September 9, she returns to the Playhouse. As part of the annual gala — which this year features “Hamilton” Tony Award nominee and Grammy winner Jonathan Groff — the 1966 Staples grad receives the Leadership Award.

It’s been in the works even before Sheffer was born. 

Starting in the 1930s, her grandparents spent summers and weekends in Westport. (Their property, on the corner of Cross Highway and Bayberry Lane, predates the Merritt Parkway and Nike site — which became the Westport Weston Health District and Rolnick Observatory.)

As a child, Sheffer’s grandparents and parents took her to the Playhouse. She still recalls sitting in those red seats, for Friday afternoon children’s shows.

The Westport Country Playhouse, back in the day.

At 15, she became one of Gilbert’s ushers. The Playhouse calendar included 12 shows every season, from Memorial Day to Labor Day.

The set would be struck Saturday night. A new one was constructed on Sunday. On Monday, the next play opened.

Going to the Playhouse was “the social event” of the week, Sheffer remembers. “People kept their own seats, and their own days of the week, for years.”

Much has changed — from summer habits to entertainment options to theater itself.

But Sheffer’s commitment to the arts — and the Westport Country Playhouse — never wavered.

Ann Sheffer

After graduating with a degree in theater from Smith College, she earned a master’s in theater administration from Tufts, and an MBA from the University of Washington. Sheffer worked with many non-profit arts groups, serving on boards at the local, state and national levels.

In 1999 — after decades assisting a variety of Westport organizations — Sheffer was asked to help plan the Playhouse renovation. During that long but fruitful process, she championed its history and cultural significance. That includes preserving posters from the Playhouse’s long history. They’re now displayed in the lobby.

She helped procure $5 million in bond money from the state. She also negotiated a $2 million grant to name the adjacent barn for Lucille Lortel, along with annual funds for new plays.

Sheffer has long supported the Playhouse’s education programs. Her brother Doug was a props apprentice in 1968. (That’s why every play featured furniture and other items from the Sheffer’s home — including Sheffer’s mother’s high school diploma, which hung on the wall when Shirley Booth starred in “The Desk Set.”)

In 1968, the Westport News profiled Playhouse apprentices. Doug Sheffer is shown in the photo at right.

Sheffer was a trustee until 2015 — “15 amazing years working with Joanne Woodward, Annie Keefe and a dedicated board” that completely transformed an old, leaky and unheated barn into a theater for the next generation.

When she accepts her award at the September 9 gala, Sheffer will no doubt speak about what the Playhouse has meant to her, for so many years.

She may also weave together some of the strands that continue to tie the Westport Country Playhouse to the rest of the community. For example, the Susan Malloy Lecture in the Arts — named for Sheffer’s aunt, and set for September 11 — will feature a panel discussion on “Falsettos.”

Interestingly, in 1994 Staples Players presented that groundbreaking show about gay life as a studio production. The principal did not want it to be shown at the high school — so the Playhouse offered its stage.

The same stage that — 30 years earlier, and more than 50 years ago now — was a home away from home for a generation of Staples Players.

Including a very passionate, and impressionable, Ann Sheffer.

(The Westport Country Playhouse Gala on Saturday, September 9 begins with a 5:45 p.m. cocktail party. A presentation to Sheffer, a performance by Groff and a silent auction follow. All proceeds benefit the WCP’s work on stage, with schools and throughout the community. For more information and tickets, call Aline O’Connor at 203-571-1138, or email aoconnor@westportplayhouse.org.)

The Westport Country Playhouse today.