Molly Conole’s new one-woman musical play, Seaglass, Quilts & Song: Life in Pieces, had its premiere at the Martha’s Vineyard Playhouse over the weekend, playing to packed houses Friday and Saturday nights.

The theatre had to add an extra row of seats for Saturday’s performance to fit in all the fans who wanted to see the autobiographical show, directed by playhouse artistic director MJ Bruder Munafo.

Pin-drop silence alternated with wild applause throughout the engaging, confessional, sometimes very funny and occasionally heartbreaking 90-minute play. Most Islanders still may know her simply as “that woman with the pretty voice,” or “the helpful store clerk,” Ms. Conole told the audience. “Those are me too, but there is more to my story.”

In 12 original songs, two folk songs and a series of stage vignettes, Ms. Conole traced her life with unflinching frankness: the delight of living with her adored young mother, the trauma of childhood abduction by her unstable father, the heartaches of early love and the supreme joys—with their balancing terrors—of long-awaited motherhood.

“I smile and laugh, but that doesn’t mean I’m not struggling,” Ms. Conole told the audience. — Mark Alan Lovewell

Finding a loving husband and giving birth to two daughters eased Ms. Conole’s childhood pain, though the loss of her mother still hurts. She also revealed that her oldest daughter has come out as lesbian, her second child is transitioning to male, and her husband, who seemed distant for years, recently came out to her as bisexual.

“I don’t remember applying for the LGBTQ family grand prize,” Ms. Conole said to laughs, before turning grave: “My family feels so vulnerable now, at risk of judgment.”

The Vineyard, where she began vacationing as an infant, provides an important foundation to the show. “It’s been a part of me since I was six months old. All day long I just lived on the sand.”

While she has lived in more than a dozen mainland locations during her career, including a stint as a performer at Disney World, “I always found my way home here to the water,” she said.

The theme of the show comes from an insight during her first pregnancy, 20 years ago. Suddenly, she saw herself as a piece of sea glass in formation, tumbling in the Vineyard waves, sharp edges wearing smoother one wave at a time, year after year. Last autumn, she said, the thought “exploded” back into her mind with compelling urgency as the basis for a solo performance.

“I wrote four songs, three scenes and a grant proposal in one day. It takes a piece of sea glass 20 to 100 years to turn into a jewel. Since I turned 60, maybe I’m almost a jewel.”

In order to focus on the play, Ms. Conole negotiated leaves of absence from the Martha’s Vineyard Community Chorus and the choir at First Congregational Church of West Tisbury, where she is associate music director. She also took the past week off from her job at Educomp in Vineyard Haven to prepare for the performances.

Quiltmaking provides the second metaphor for the play, bringing together the separate parts of what she called “my follow-the-rainbow life, my life in pieces, told in songs also built in pieces.”

“Built in pieces,” though, is not a metaphor. A grant from the Martha’s Vineyard Cultural Council paid for the purchase of an electronic looping station, a $500 desktop console with slide controls for digitally pre-recorded sounds. Ms. Conole used the unit to add layered tracks of her own voice, and occasionally piano, as vocal backing for her live performance.

Her backing vocals wordlessly rose and fell like the ocean waves that are Ms. Conole’s touchstone, wailed sadly for the child left alone long ago or percolated with a don’t-worry-be-happy bounce, as she sang into the microphone. Perhaps the most affecting use of the looping device was on a song of love for Ms. Conole’s late mother, a virtual duet in which the woman on stage fell silent and rapt as she listened to words of devotion sung as if from beyond the grave.

Tearful moments like this, and some of her fears for her family, were rare insights into the heart of a trouper who is rarely seen without a smile.

“I smile and laugh, but that doesn’t mean I’m not struggling,” Ms. Conole said. “Being cheerful is my choice—a choice I make every day, sometimes every minute. I have seen depths and survived … But I know that out of darkness comes the light. I have seen it. Light shines through the colors of broken glass.”

At her suggestion, a lobby art exhibition complements Ms. Conole’s themes with stained glass pieces by Pia Centenari-Leonard and Barney Zeitz, quilts by Jan Paul and photographs of sea glass by Paul Doherty. The works remain on display through May 30.

The playhouse’s spring series of one-woman shows continues May 17 and 18 when Ms. Bruder Munafo directs actress and singer Shelagh Hackett in Kiss Me I’m Irish. Tickets and information are at