A father meets three versions of his son in “A Number” at Ancram Center for the Arts; a long-married couple upends their children’s assumptions in “Grand Horizons” at the Ghent Playhouse. Fall theater also heads underground for “Ghost Stories of the Hudson Valley” at Widow Jane Mine and spills across Newburgh for the Fringe Festival. In Garrison, “The Glorious Death of Comrade What’s-His-Name” turns Stalin-era desperation into musical farce. Later, “Darlin’” traces the secrets passed between mothers and daughters, while “Legacy” follows a family story back to Nazi Germany. There’s also improv, Pirandello, and a theater deathmatch decided by the audience.
“A Number” at Ancram Center for the Arts
October 1-11 in Ancram
A father confronts three versions of his son—two of them clones—in Caryl Churchill’s compact, unsettling psychological thriller. Written in 2002, “A Number” uses speculative science to examine parenthood, identity, nature versus nurture, and what makes any individual irreplaceable, questions that carry added weight in the age of AI. Jeffrey Mousseau directs Drew Ledbetter and veteran Broadway actor John Wojda, with one performer portraying all three sons. Churchill, whose plays include “Cloud 9” and “Top Girls,” compresses an extraordinary amount of drama into one hour.
“Ghost Stories of the Hudson Valley” at Widow Jane Mine
October 2-4 in Rosendale
Theatre on the Road descends into the Widow Jane Mine for an evening of history, folklore, and things that refuse to remain buried. The family-friendly production dramatizes the lives of four figures who helped shape the Hudson Valley, returning them from centuries past to share their stories inside the cavernous former cement mine. Between vignettes, the mysterious Night Watchman holds the evening together with tales of regional spirits and unexplained happenings. The room-and-pillar mine forms a fittingly eerie natural amphitheater, complete with shadowy recesses, resonant acoustics, and a subterranean pond behind the stage.
“Grand Horizons” at the Ghent Playhouse
October 2-11 in Ghent
After 50 years of marriage, Nancy casually announces over breakfast that she wants a divorce—and her husband, Bill, appears perfectly agreeable. Their adult sons are another matter. In Bess Wohl’s Tony-nominated comedy, the couple’s children descend upon the retirement community of Grand Horizons, determined to save a marriage they understand far more poorly than they imagined. What follows is a funny, candid examination of long relationships, family mythology, aging, and the inner lives children seldom permit their parents to possess. Wohl, whose plays include “Small Mouth Sounds” and “Liberation,” balances sitcom-ready complications with sharper questions about desire, compromise, and starting over.
Rivertowns Improv Fall Festival
October 16-17 in Croton-on-Hudson
No scripts, no safety net, and—if things go according to plan—no two shows remotely alike. Produced by Blind Tiger Improv, the inaugural Rivertowns Improv Fall Festival brings 18 unscripted comedy acts to the Croton Academy of Arts for two packed days of performances, workshops, hangouts, and after-parties. The bill draws teams from the Hudson Valley, New York City, and beyond, with headliners including puppet-comedy duo Josh and Tamra, Albany’s long-running Mop and Bucket Company, and Hudson Valley Improv. Established ensembles share the festival with newer groups, while workshops invite performers to sharpen their storytelling, characters, spontaneity, and collaborative mischief.
Newburgh Fringe Festival
October 16-18 in Newburgh
For one weekend, Newburgh becomes an expansive stage as the city’s Fringe Festival presents nearly 50 performances across multiple venues. The sprawling program favors variety and experimentation: new plays and reinterpretations of existing works share the calendar with sketch comedy, standup, puppetry, dance, live music, clowning, and other hard-to-classify acts. Full-length productions sit alongside compact performances, allowing audiences to assemble their own itineraries and encounter artists at different stages of development. More than a theatrical marathon, the festival encourages visitors to move through Newburgh itself, turning its performance spaces—and the streets connecting them—into parts of the experience.
The Crowbait Club at Avalon Lounge
October 18 in Catskill
Theater becomes a contact sport at the Crowbait Club, a monthly “theater deathmatch” presented by Columbia County Players and the Hudson Observer. Playwrights arrive with original plays of 10 minutes or fewer responding to a prompt—the inaugural theme is “Doors”—then recruit willing audience members as actors. Following a two-minute rehearsal, the hastily assembled companies take the stage and the audience votes for its favorite. The winning playwright and cast earn monthly champion status, while the script is published in The Hudson Observer. Hosted by actor Tristan Geary, the free series welcomes experienced performers, first-timers, and spectators.
“The Glorious Death of Comrade What’s-His-Name” at Depot Theater
October 30-November 22 in Garrison
An unemployed dreamer with no musical ability decides that becoming a tuba player might improve his prospects under Stalin. When that fails, Semyon begins plotting a spectacular death—only to attract a revolutionary opportunist and a parade of schemers eager to turn his demise into political theater. Adapted from Nikolai Erdman’s banned 1928 play “The Suicide,” this world-premiere musical comedy skewers fame, fascism, and the absurdities of power. Director John Christian Plummer calls it “the lovechild of Mel Brooks and Bertolt Brecht.” Raymond Bokhour, Broadway’s longest-running Amos Hart in “Chicago,” stars alongside Douglas Goodhart, Christine Bokhour, and Maia Guest.
“Darlin’” at Bridge Street Theatre
November 5-15 in Catskill
Bridge Street Theatre presents the world premiere of Michelle Carter’s “Darlin’,” a time-hopping family drama about mothers, daughters, and the complicated inheritances passed between them. Moving across generations, the play examines how secrets, withheld words, and tangled loyalties shape women struggling to define themselves both through and apart from their families. Carter approaches the subject with wit and emotional candor, finding humor amid resentment, longing, and the difficult work of forgiveness. At its center is the desire to be fully seen—and the freedom that comes with claiming one’s own identity.
“Legacy” at the Old Dutch Church
November 12-21 in Kingston
Written and directed by Voice Theatre artistic director Shauna Kanter, “Legacy” draws on her family history to tell a suspenseful story of courage, fear, and buried truth. In 1968 Philadelphia, Sarah investigates her late father’s claim that he rescued Bertolt Brecht’s children from Nazi Germany. Her search returns to 1939, when David and his wife, Vera, traveled to Berlin under false identities to save a Jewish photographer and her children from the Gestapo. Archival projections, film, song, and original live klezmer music accompany the action. Performances are held in Bethany Hall.
Pirandello at the Phoenicia Playhouse
December 4-13 in Phoenicia
Woodstock Fringe and the Phoenicia Playhouse collaborate on an evening of dramatic contrasts by Italian playwright and Nobel laureate Luigi Pirandello. In “The Man with the Flower in His Mouth,” a chance late-night encounter at a railway cafe becomes a haunting meditation on mortality, attention, and the intensity of ordinary life. “Chee-Chee” takes a more comic turn, following a charming rogue who survives through bluffing, financial maneuvering, and psychological gamesmanship. Together, the one-acts display Pirandello’s gift for placing unstable identities beneath social masks—and finding both dread and absurdity there.
