Chilina Kennedy was a military kid. Born in New Brunswick, she lived everywhere -- Australia, England -- you name it.

Kennedy's first paid gig was acting in children's theatre.

"I was in high school and it was a great outlet for creative feelings."

After musical theatre training at Sheridan College, Kennedy had an audition with the Charlottetown Festival.

Coached by teacher Christina James, she landed the part of Anne in the Festival's flagship show Anne of Green Gables. Quite a feat for a kid just out of school.

"That was eight years ago and I've been working ever since.

Kennedy is known to Theatre Aquarius audiences for her roles in Jesus Christ Superstar and last season's Christmas musical, The Seussical.

Now at the Shaw Festival, she's playing Eileen Sherwood in the vintage musical Wonderful Town.

"In a way, Eileen is the straight role. She's sweet, attractive and very manipulative. But of course she manages people in the very nicest way."

Wonderful Town premiered on Broadway in 1953 and won a Tony Award as best musical. With music by Leonard Bernstein, a book by Joseph A. Fields and Jerome Chodorov, not to mention clever lyrics from Betty Comden and Adolph Green, it was a huge hit.

Based on Ruth Sherwood's 1938 book My Sister Eileen, Wonderful Town is a musical in old-fashioned Broadway traditions.

In other words, we're talking about a good story, toe-tapping music and lyrics that make you laugh and cry.

"I have to find a way into the period," Kennedy laughs. "Everything about me is 2008. Today things are casual. They weren't so easy back then... people had a public and a private persona. Women wore their little gloves and put on their smart hat. Now it's jeans and a shirt. That's quite a transition."

Kennedy likes the journey she is taking. "I love going to the theatre and discovering different time frames. On a personal level, I like the process of discovering a character.

"With this particular show, I love the fact it's based on truth. There really was an Eileen Sherwood and she went to New York City with her sister, Ruth, and they had all these wonderful adventures. It's a journey back to a New York City that may or may not have really existed."

Anyone who loves New York will have fun with the goings-on here.

"The musical is set in Greenwich Village when it really was the centre of bohemian culture. The characters Eileen and Ruth meet are quintessential New York types. The whole show revolves around the experiences of these two young women trying to make it in a world full of competition."

On Broadway, Wonderful Town found connection with the sort of innocent creatures who migrated to New York City looking for happiness and success. In a sense, its more contemporary counterpart would be Stephen Sondheim's Company, a musical that looks at survival of the fittest in a less-charming New York of the early 1970s.

"In real life, Eileen Sherwood was engaged to a wealthy polo player, but she gave him up for a shot of fame in New York City. When she and her sister, Ruth, sing their lament about leaving Ohio for uncertainty and confusion in Manhattan, they suggest something so many young women went through in those days.

"I guess in some ways I'm like Eileen Sherwood. She seizes opportunities and takes advantage of them. Well, so do I."

Gary Smith has written on theatre and dance for The Hamilton Spectator for more than 25 years.

Showtime

What: Wonderful Town

Who: Shaw Festival

Where: Festival Theatre, Niagara-on-the-Lake

When: In repertory now through Oct. 5

Tickets: 1-800-511-7429