Over the years, the Valley has sent some talented playwrights into the world — the late Wendy Wasserstein, a Mount Holyoke College graduate, is one notable name — but few can rival the success of Annie Baker, the 1999 Amherst Regional High School graduate, who has a Pulitzer Prize, a MacArthur Fellowship, and a number of other awards to her credit.

The Chester Theatre Company has been a fan of Baker’s work, previously staging two of her plays, “Body Awareness” and “Aliens.” And to finish its 2023 season, CTC is now presenting “Circle Mirror Transformation,” which won an Obie Award in 2010 for the best new American play.

CTC’s production of “Circle,” a mix of comedy and drama about a group of strangers making unexpected connections in an acting class, has some interesting connections of its own, including featuring two performers who represent something of a pair of bookends in the career of Daniel Elihu Kramer, the play’s director.

Kramer has his own connections to CTC: He’s the theater company’s former artistic director, where he served from 2015 through last year and previously directed the production of “Aliens.”

And with “Circle Mirror Transformation,” which will have 11 showings from Aug. 11 (tonight, Friday) through Aug. 20, Kramer says CTC will complete a trio of sorts of Baker’s work, since all three of the plays they’ve staged are set in the fictional town of Shirley, Vermont.

“That’s kind of a cool bonus to have,” said Kramer, the chair of the Smith College Theater Department and a longtime professor at the school. “The other thing that’s really appealing about (“Circle”) is that it celebrates theater. It’s something the performers and the audience can both appreciate.”

(Interesting footnote: Baker, who has lived in New York City for years but also teaches at the University of Texas at Austin, previously wrote a brief history of her imaginary Vermont town, which among other things noted that public nudity was permitted in Shirley until 2008.)

“Circle Mirror Transformation” follows five would-be thespians in an adult drama class over a six-week period; the actors rehearse in a community center. It’s a pretty disparate group that would seem to have little in common.

Marty, the workshop leader, is a 50-something earth-mother type; her husband, James, is a slightly older academic. Schultz, who’s 48, is a lonely, divorced carpenter who still wears his wedding ring.

Then there’s Theresa, a mid-30s actor who’s moved to town after failing to crack New York’s theater world. The fifth student, Lauren, is a moody teen who hopes taking the class will give her a leg up when she auditions for a lead role in her high school musical.

There are plenty of laughs as the actors pick their way through what seem like clichéd exercises Marty introduces: pretending to be a tree, word games, imagining you’re one of the other actors and describing “yourself” in a monologue.

“Are we going to be doing any real acting?” Lauren complains at one point.

But Kramer says these “goofy exercises,” aside from offering an affectionate nod to the spirit of theater, also serve as a means to introduce the characters to one another, which in turn offers more details from their fictional lives, where the heart of the play resides.

“Beyond the funny scenes, there’s another story that’s bubbling just under the surface,” said Kramer. “One of the pleasures of the play is that if you pay attention to what people are saying, you’ll be rewarded. And that’s true of all of (Baker’s) work … she has a lot of empathy for her characters.”

He notes that each part of “Circle” represents one week of the six week acting course, and that “people’s lives change over those six weeks — they won’t be the same.”

Baker has won particular praise over the years for her dialogue, including the way she uses the awkward stops and starts that can occur when people are speaking, particularly when they first meet.

In the introduction to “Circle Mirror Transformation,” she writes that these pauses a nd silences can seem to be slowing the play down, and that actors and directors might feel the need to pick up the pace.

Don’t do it, she says: “Without its silences, the play is a satire, and with its silences it is, hopefully, a strange little naturalistic meditation on theater and life and death and the passing of time.”

Real-life connections

Kramer says the passage of time is reflected in his own production of “Circle Mirror Transformation.” In spring, he was searching for someone to play James, and on a whim he contacted an old friend from Yale Drama School, Alex Draper, a veteran actor who teaches theater at Middlebury College in Vermont.

“I said ‘Any chance you would be available from July 18 to August 20?’ and he said he would be,” said Kramer. “It is such as treat to be working with Alex again after all this time. He was in my production of ‘Twelfth Night’ at Yale for my thesis project, and we haven’t done anything together since.”

Playing Lauren, meantime, is Hero Marguerite, a recent graduate of Smith College who majored in theater and worked closely with Kramer during her time there; she was his advisee. She was also an intern at CTC, and the fact that she’s now making her stage debut with the company “is really a thrill for all of us,” said Kramer.

Two other actors he’s worked with previously at CTC are Joel Ripka, who plays Schultz, and Tara Franklin, who appears as Theresa. Franklin, a veteran performer from Berkshire County, is now the co-artistic director of CTC along with her husband, James Barry.

Kramer says he hasn’t worked previously with Corinna May, who plays Marty, but notes that she has a lengthy resume that includes past roles at CTC, on Broadway, and at Shakespeare & Co. in Lenox, among other places. She also won two Berkshire Theatre Critics Awards, known as the “Berkies,” in 2021-2022.

To give all the actors a chance to get to know each other a little better, Kramer says he “borrowed” the scene from Baker’s play in which the five characters perform monologues as someone else in the group. He introduced the exercise at the beginning of rehearsals for “Circle Mirror Transformation” in July.

“It’s not the way I usually do things, but having everyone interviewing each other really gave us a sense of connection,” he said. “There was so much generosity and some really interesting editorial touches. Some of it was quite moving.”

He liked the experience so much, he says, that he’s planning on adding it to his beginning acting class at Smith this fall.

As he and the cast did their final work to get ready for opening night, Kramer said he was conscious of one other thing: directing the play without having to worry about all the other things he was responsible for as CTC’s artistic director “has really been a relief.”

Tickets and additional information for “Circle Mirror Transformation,” playing through Aug. 20 at CTC at Chester Town Hall, are available at chestertheater.org.

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