THE DIARY OF AN OREGON TRAIL SPINSTER To Play Fertile Ground Festival 2026

A new single-woman show, THE DIARY OF AN OREGON TRAIL SPINSTER, written, produced, and performed by Brenan Dwyer, will be presented as part of the 2026 Fertile Ground Festival of New Works in Portland, Oregon.

The production will run April 24–26, 2026 at 21Ten Theatre.

Directed by Genevieve Fowler, the 60-minute multimedia theatrical work follows an elder millennial woman navigating a reimagined version of the Oregon Trail video game. The piece incorporates projection, storytelling, and performance elements to explore themes including ambition, mental health, relationships, and artistic identity.

The story centers on a character known as “The Spinster,” who reflects on her life through a series of confessionals while journeying toward Oregon territory. Along the way, she examines personal choices, relationships, and the challenges of pursuing a creative life.

“I was drawn to The Diary of an Oregon Trail Spinster because it has everything I want out of a theater piece today—a story of real, human struggle and resilience wrapped in the kooky humor I expect from a Best Friend and presented through a multimedia design that evokes the nostalgia of the canonical 90s experience,” said director Genevieve Fowler.

Playwright and performer Brenan Dwyer added, “The Diary of an Oregon Trail Spinster is my ode to this generation of strivers, and a testament to my personal journey that has been full of high mountains and deep valleys on my own journey to artistic fulfillment, financial security, and securing romantic and family love.”

The production features scenic design by Drew Foster, video design by James Raymond, lighting design by Brandon Baruch, sound design by Paul Fraser, costume design by Margot LeDuy, stage management by Jake Wyse, and creative producing by Emma Zakes Green.

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