Last Friday evening, a mother and daughter walked into the Performing Arts Center wearing matching pink dresses. Many other mothers and fathers walked in holding the hands of their young children, some skipping and jumping with excitement as the arrived to see the Island Theatre Workshop’s production of Annie. The play opened last weekend and continues with performances on Thursday through Sunday.

Yes, it is a hard knock life. — Jeanna Shepard

The lights came down in the house and the band began to play. The opening notes, as well as each of the other songs that followed, were very familiar to many. But for some parents who had not seen the play since they were young, the story’s darker themes, with roots in the Depression-era comic strip by Harold Gray, echoed louder than the orphans’ songs of hope.

Vineyarder Moira Silva, who attended the show with her son Owen, said that when she was a girl, her sister had Annie bed sheets and they both would stand on the bed and belt out the words to every song.

“When I was little, I totally missed the political overtones,” she said, adding that she was surprised to see how the political situation of 100 years ago so closely mirrored that of today.

This was one of the reasons Kevin Ryan, director of the play and artistic director of the Island Theatre Workshop, chose the play for this summer.

Annie presents a story and music familiar to many. — Jeanna Shepard

“We as a people in this country are, in my opinion, in a very dark and scary place right now,” Mr. Ryan said. He said Annie may not have been his first choice if it weren’t for the recurring themes. “We have people scared to death about losing their jobs, people that are on relief, what in the 30s was the breadline.”

“And we have a huge problem in this country with the foster care system and the adoption program,” he added. “Here we are, 2017 and we’re having the same issues. To look around at the reality of this country right now... I think this show is really appropriate.”

But Mr. Ryan added that he sees Annie as a story of unwavering hope. The young girl at the center of the action sets her eyes on the horizon and keeps marching bravely forward. “Tomorrow will come,” Mr. Ryan said. “What are we going to do about it? How are we going to make it better?”

The young cast seemed to have the answer, energized with a sense of optimism. Isabelle Murphy, a rising eighth-grader at the Edgartown school plays Annie with a steady voice and an “aw, gee” kind of gumption. West Tisbury school fourth-grader Molly Crawford, as orphan Molly, leads the packs of foundlings with a bright face and a confident, timely delivery. The rest of the orphans peep like pinkletinks behind her.

Shelley Brown plays Miss Hannigan, Paul Doherty plays Rooster. — Jeanna Shepard

Paul Padua plays a charmingly daft Roosevelt, Shelley Brown plays Miss Hannigan and Brad Austin is Oliver Warbucks. Jennifer Knight plays Mr. Warbucks’ assistant, the graceful Grace Farrell. Rooster is played by Paul Doherty, and Lily is played by Alysha Norbury. Music direction is provided by Bill Peek, with a five-member orchestra playing the score.

And Sandy is played by a live dog who only once ignored a cue in favor of staring out at the audience.

Mr. Ryan says he intends to continue staging family-oriented shows in the summer season. When his son Jonathan was little, he said, it was a constant challenge to find evening activities for children once their schoolwork was put away. Mr. Ryan said he was happy to provide a fun outing for children, along with the parents they are so lucky to have.

Remaining performances of Annie are August 3, 4 and 5 at 7:30 p.m. and a meet-and-greet matinee on August 6 at 3 p.m. All shows are at the Performing Arts Center.