Santa Cruz Shakespeare goes ‘Into the Woods’ — and strikes gold

This summer, Santa Cruz Shakespeare’s four-show season themed “No One Is Alone,” includes a bold departure from doublets and daggers in favor of cloaks and curses, producing its first musical in decades with Stephen Sondheim and James Lapine’s “Into the Woods.” It’s a daring shift in artistic direction — and it’s happening not in a velvet-curtained theater, but at the Audrey Stanley Grove at DeLaveaga Park, their open-air amphitheater nestled amid towering trees.

Premiering on Broadway in 1987, “Into the Woods” is one of Stephen Sondheim’s most beloved — and most philosophically rich — musicals. The book by James Lapine weaves together several familiar fairy tales: “Cinderella,” “Jack and the Beanstalk,” “Little Red Riding Hood” and “Rapunzel,” among others. But rather than simply retelling them, the show delves into what happens after “happily ever after.” Don’t be fooled by the fairy tale trappings — this isn’t your childhood bedtime story. It’s Sondheim, after all, and in his hands, the woods are a tangled place of moral ambiguity, dashed dreams and unintended consequences.

With its blend of whimsy and wisdom, “Into the Woods” is a fitting choice for an outdoor venue — nature looms large in the story, both literally and metaphorically. Still, I’ll admit I was apprehensive. How would SCS pull off Sondheim with only a live piano and a mostly bare set? But as the sun dipped below the horizon and the lights came up on Act I, my doubts melted away. Something magical happened on that stage.

From the first note, it’s clear this is not a conventional “Into the Woods.” It’s an entirely different experience — staged with the playfulness of commedia dell’arte and featuring an ensemble cast of just 11 actors, many of whom double in roles. And, it all works beautifully.

The plot centers on a Baker and his Wife, cursed with infertility by a vengeful Witch. To break the spell, they must venture into the woods and collect four magical items: a cow as white as milk, a cape as red as blood, hair as yellow as corn, and a slipper as pure as gold. Along the way, they cross paths with other fairytale characters, each on their own quest.

Act I ends with everyone seemingly getting what they want. But Act II, in true Sondheim style, unravels those victories. A vengeful Giant descends, tragedy strikes, and the characters must confront the consequences of their choices. The musical becomes a meditation on community, responsibility and the messy truths behind the stories we cling to.

Director Jerry Lee brings a clear vision to the production: one that balances the whimsy of childhood stories with the darker truths that follow. Inventively staged on a two-level set that includes a working trap, the production feels expansive and dynamic. Kudos to Lee and the creative team for using every available resource to bring this world to life with ingenuity and flair.

And, while some might expect to miss the grandeur of a full live orchestra, the production never felt musically thin. Music director Luke Shepherd performs live on piano alongside a pre-recorded score, conducting the cast through Sondheim’s famously intricate music with clarity and sensitivity. The result is a full-bodied sound that supports the vocal performances splendidly.

Costume designer Austin Blake Conlee meets the challenge of multiple roles with creativity and wit. Costumes are layered, transformable and often shed or revealed onstage, allowing seamless character transitions that feel both practical and playful.

At the heart of the cast is Daniel Harray, delivering a standout double performance as the Narrator and the Mysterious Man. With wit, warmth and a touch of melancholy, Harray shifts effortlessly between storyteller and spectral figure, serving as both moral compass and cautionary voice.

Charlotte Boyce Munson commands the stage as the Witch, blending gravitas, wicked humor and vulnerability to a role that demands constant reinvention — from snarling antagonist to grief-stricken mother, she navigates Sondheim’s demanding score with ease and nuance. 

Tyler Nye and Melissa WolfKlain, as the Baker and his Wife, respectively, share a delightful chemistry that deepens the moral core of the piece. Their journey anchors the show’s message that actions, even small ones, ripple outward.

Lori Schulman delights as the conniving stepmother, especially during her droll “Careful My Toe,” accompanied by Elliot Sagay and Alex Cook as the horrid stepsisters — played in drag with exaggerated flair. The two then reappear as the predatory wolves and later as the over-the-top, love-struck princes in the uproarious duet “Agony.”

Jordan Best offers a haunting vocal performance as Cinderella’s mother, the spirit in the tree. In contrast, Mai Abe’s Little Red vocals often strayed from the mark, but her boundless energy and irresistible charm more than made up for it. 

Other ensemble members, including Justin Joung (Jack) and Ciarra Stroud (Cinderella/Rapunzel), brought depth and vitality to their roles, shifting smoothly between comedy and poignancy. 

The Grove itself becomes an extension of the set with the illuminated trees expanding the visual scope. By Act II, as the fairy tale veneer falls away, another moment of theatrical magic arrives — the sonic boom of the Giant’s footsteps and the cracking of unseen branches evoke a “Jurassic Park”-style sense of dread. The effect was thrilling.

Although “Into the Woods” is nearly 40 years old, its themes continue to resonate powerfully in 2025. At its core, the show is about what happens when personal desires clash with the needs of the greater good. In today’s polarized climate, “Into the Woods” becomes more than a musical — it’s a metaphor. The show asks: What do we do when our institutions fail us, when our stories no longer offer clear answers? And more crucially: Can we come together to rebuild?

Santa Cruz Shakespeare’s decision to theme its season around “No One Is Alone” — a line sung at the show’s emotional climax —  is a thoughtful act of curation. It’s not a sugary reassurance. It’s a reckoning — one that asks us, like its characters, what we owe to each other, and what it truly means to be part of a community — and what part we’ll play in writing the next act, even when the path is uncertain, the woods are dark, and the endings unclear. This is the power of “Into the Woods.” It’s a mix of funny, moving, strange, and unforgettable. And under the trees, under the stars, it feels exactly right. Don’t miss it!

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