Arlene Hutton’s Nibroc Trilogy begins with one of the sweetest and funniest courtship scenes in contemporary drama. Two young people meet on a cross-country train at the beginning of World War II. Raleigh is a talker and a teaser, May shy and proper, and she’s both affronted and tickled by his attentions. Turns out they are from adjacent small towns in Kentucky, and over the next couple of years they conduct a hesitant courtship and finally marry.

He has a medical condition that keeps him from contributing to the war effort either as a soldier or a factory worker, while she advances in her teaching profession because so many men are at war. But when the war is over, she loses her job. He, meanwhile, is beginning to make a name for himself as a writer.

The three-play cycle follows May and Raleigh through a dozen years of marriage, into the early 1950s. Like all Chester Theatre Company’s productions, the plays are small-scale, but harbor big themes—including, in this case, women’s roles and racial prejudice, in an era when, like today, American society was going through seismic changes.

“Arlene Hutton has this amazing ability to interweave the epic and the incidental, the intimate and the large-scale societal issues,” says Chester’s artistic director, Byam Stevens. “And she manages to land all these things within the family group in a way that seems very organic.”

This summer the 20-year-old company is taking on a large-scale challenge: devoting most of its four-play season to these three interconnected plays. The second play in the trilogy, See Rock City, is now playing. Next week number three, Gulf View Drive, opens. And on two weekends this month the whole cycle will be performed on a single day— including a Kentucky-style ice cream social and box dinner between shows.

I visited Chester a couple of weeks ago to have a look at the creation process. The two leads, Allison McLemore and Joel Ripka, were performing the first play, Last Train to Nibroc, while rehearsing both the other plays by day. I was curious to find out how they were keeping these three balls in the air.

“We’ve had some ‘Oh my god, are you kidding me?’ moments,” said McLemore. “It’s a challenge, but it’s also really informative. We’re living out our characters’ backstories on stage—the kind of stuff that normally, as an actor, you’re creating in your imagination. Starting rehearsals on the next play, I have the advantage of already knowing May—what her buttons are, what things make her happy, what the scope of the character is.”

“But then,” Ripka added, “when we do the first play in the series tonight, we have to rewind. We have to forget what happens later, all that history we’ve built, and pretend we’re meeting again for the first time.”

The Nibroc Trilogy: See Rock City, through Aug. 8; Gulf View Drive, Aug. 11-22; entire cycle Aug. 14 and 21. Chester Theatre Company, Chester Town Hall, (413) 354-7771, www.chestertheatre.org.