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The Chester Theatre Company performs in idyllic summer surroundings, in an old town hall amid the green hills of the Berkshires. But its 25th season kicks off with “Madagascar,” an enigmatic play with a tricky structure and a central figure who never appears onstage. This troupe doesn’t do easy.

“No, we don’t,” artistic director Byam Stevens says with a cackle. “We’ve developed an audience that is a thinking audience, an audience that likes to be — well, challenged is such an overused word. It seems so conflict-oriented. We’re not here to challenge anybody. We’re here to encourage people to listen and consider.”

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“Madagascar,” by J. T. Rogers, will be followed by Sharr White’s “Annapurna,” Caryl Churchill’s “A Number,” and Jessica Dickey’s “The Amish Project,” a one-woman show performed by Allison McLemore that is a fictional exploration of a real-life schoolhouse shooting. Plus there’s a three-night return of Leslie Ayvazian’s “High Dive,” a one-woman show performed by Jennifer Rohn, in which the audience gets to read some of the lines.

All more or less challenging works, drama or comedy. And in a year when gender parity is a subject of major discussion in the theater world, three out of five are written by women, but that’s a coincidence. This season is simply a celebration of the contemporary playwright, Stevens says, ranging from the eminent (Churchill) to the emerging (Dickey), and tackles “big ideas” about how we live now.

“Madagascar” is set in a hotel room overlooking the Spanish Steps in Rome that the three characters occupy at separate times. The wealthy and stylish Lilian, played by Debra Jo Rupp, speaks to us from five years ago. Her daughter June, played by Kim Stauffer, was there a few days ago, working as a tour guide. Nathan, played by Paul O’Brien, is there now; he was best friend to Lilian’s late husband.

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Added to the strange time frame is the fact that much of the discussion is about June’s brother Gideon, his whereabouts and his intentions. To say much more renders spoilers, but the play tackles big questions like how much of a mystery we are to each other, and what responsibility we bear for others’ decisions.

“You get to the end of it and you still don’t know why the events that happened have happened,” Stevens says. “You have clues. It’s like ‘Rashomon,’ I guess. You have three different people telling you their version of a series of events. And you come to the end and have a pretty strong suspicion that none of the three have the full story.

“It’s a beautifully written play, it’s so deeply felt, and by the end, it’s informed by this hopeful thing — each one of these people who is trying to figure out this very painful event in their life does so in the full belief they will arrive at an answer that gives them peace,” he says.

Rupp is best known for her role as Kitty Forman on Fox’s “That ’70s Show,” but she is a regular in the Berkshires, having appeared at Chester in “Body of Water” and at Barrington Stage Company in the hit, “Dr. Ruth, All The Way.” O’Brien is new to Chester, although his son Tom has played there in “The Retreat From Moscow.”

Stauffer performed in the troupe’s “Crime and Punishment” in 2011 and says there’s a sense of artistic community at the company.

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“For a lot of us, the reason we love coming here is because the material Byam chooses, it’s a wonderful adventure to dive into the roles,” Stauffer says. “It’s a little bit off the beaten path, and it’s a great place to come and take risks as an actor, to embark on that journey and feel like you’re in a safe place to do it.”

The company’s annual budget is just under $300,000, Stevens says, roughly triple what it was when he took the job in 1998. “I think what we’ve managed to accomplish for that is clearly a company punching above its weight,” he says.

A turning point came in 2010, when Chester, like most other companies, was hit hard by a drop in donation and foundation support after the economic meltdown. Instead of cutting back, it went big by producing all three parts of Arlene Hutton’s “Nibroc Trilogy,” including two daylong marathons of all three, complete with meals in between.

“We thought if we tightened our belts onstage, that we risked being on a downward spiral of shrinking budgets, shrinking performances, shrinking excitement from the audience, shrinking box office income,” he says. “We thought the only way to get out of this thing was to invest in this big event.

“What it did was, we got coverage from every media outlet in New England for taking on this thing at a time when everybody else was so frightened, and doing this logistically huge, complicated project,” he says. “It was fun and exciting and did what we hoped it would do. Taking risks pays off.”

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Location is another one of the reasons the company’s programming works, Stevens says. Because Chester is roughly halfway between the mainline Berkshires summer-arts corridor along Route 7 and the college-rich Amherst-Northampton area, the company’s audience is a little more diverse, he says, a little more willing to take those risks.

As actors have known for a long time, the Berkshires setting is a lifestyle bonus. Stauffer recently bought a cabin just over the border in New York state, dividing her time between it and New York City. Last Wednesday after rehearsal, she and the stage manager and assistant stage manager jumped in Center Pond in Becket.

“You finish rehearsal, and you can just take off for a hike, get out and really enjoy being in the Berkshires. It’s a huge perk, I think,” she says.

‘Aida’ from Fiddlehead

Fiddlehead Theatre Company has announced its second season as resident theater company of the renovated 1918 Strand Theatre in Dorchester’s Uphams Corner. The company will present Tim Rice and Elton John’s “Aida” (Oct. 17-26), originally scheduled for last season; “The Wiz” (Feb. 13-22, 2015) and Andrew Lloyd Webber’s “Jesus Christ Superstar” (April 24-May 3, 2015), all featuring professional casts and live orchestras.

The company continues neighborhood outreach with groups like the Boys & Girls’ Clubs of Dorchester, and has the support of Mayor Martin J. Walsh, as it did his predecessor, Thomas Menino, for whom revitalizing the Strand was a key initiative in the neighborhood.

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Tickets are $25-$45, but there are group rates, discounts for Dorchester residents and a limited number of free tickets for Boston public school students. For tickets and information, call 617-229-6494 or visit www.fiddleheadtheatre.com.


Joel Brown can be reached at jbnbpt@gmail.com.