Woodstock’s Iconic Outdoor Shakespeare Festival Marks 31st Year With Roaring ’20s Twist

WOODSTOCK, NY — For over three decades, summer in Woodstock hasn’t just been about music—it’s been an essential pillar of the Hudson Valley’s theatrical terrain. Bird-On-A-Cliff Theatre Company is thrilled to announce its landmark 31st season of the Woodstock Shakespeare Festival, kicked off this past weekend, Friday, July 31st, 2026.

This year’s production brings a bold new concept to the open-air stage: a gritty, stylized Roaring 20s gangster-themed version of William Shakespeare’s early comedy, The Two Gentlemen of Verona. Directed by David Aston-Reese, this fast-paced production takes audiences from glittering, jazz-age settings to lawless, underground territory, utilizing a chaotic backdrop of mistaken identities, rebellious outlaws, and a dramatic test of lifelong friendship.

Perched on the historic Comeau Property—just a short stroll from Woodstock’s village green—performances will run Fridays, Saturdays, and Sundays at 5:30 PM through Labor Day Weekend (September 6th).

“Bring a blanket, bring a chair, bring a picnic,” says co-founder Elli Michaels. “We invite everyone to grab a spot on the grass and lose themselves in this timeless adventure. Because the curtain falls just as Woodstock’s vibrant nightlife begins, it’s the perfect anchor for a summer evening.”

A Hudson Valley Paragon Born from NYC Roots

The festival and the company itself are the creations of Elli Michaels and David Aston-Reese, a couple who first met as working actors in New York City. Driven by a deep love for the local community that began when Michaels first visited the area around the time of the historic 1969 Woodstock concert, the duo sought to bring elite, professional theater to the Catskills. Before establishing their permanent open-air Elizabethan stage, the company pushed artistic boundaries at the Byrdcliffe Theater, even staging a historic, highly unusual production of Samuel Beckett’s Waiting for Godot with an all-female cast.

Today, Bird-On-A-Cliff is a celebrated cultural institution, keeping world-class theater completely accessible to the public on an outdoor stage bracketed by lush green woods. Admission remains entirely free.

The Noble Troupe and Fellowship of Players from Indstury Veterans to Rising Stars

The production features a dynamic ensemble of professional Hudson Valley actors who specialize in bringing high-energy, genre-bending interpretations to classical texts. Cast through competitive regional auditions at the Woodstock Town Hall earlier this spring, the performers bring physical comedy, rapid-fire banter, and intense dramatic stakes to this year’s stylized Jazz Age underworld setting. True to the festival’s tight-knit history, the company features a mix of returning festival favorites alongside fresh regional talent. This year’s cast features a mix of talent from industry veterans to up-and-coming rising stars and those in between, including Lon Haber (Valentine), Orson Bridges (Proteus), Sandra Cummings (Sylvia), Mia Barbuto (Julia), David Shakopi (The Duke), Ezra Czermerys (Speed), David Sharbowicz (Launce), Elli Michaels (Lucetta/Outlaw), Bethany Goldpaugh Brown (Atonia/Outlaw), Daphne Rosenblum (Pathina/Outlaw) and Robert Sheridan (Sir Eglamour).

Event Summary & Fast Facts:

What: Woodstock Shakespeare Festival’s Roaring 20s The Two Gentlemen of Verona

Where: The Comeau Property, 45 Comeau Drive, Woodstock, NY (Walking distance from downtown)

When: Fridays, Saturdays, and Sundays at 5:30 PM (July 31 – September 6, 2026)

Admission: FREE (Suggested donation of $10 to support Bird-On-A-Cliff, a 501(c)(3) non-profit)

More Info: Visit the Bird-On-A-Cliff Website for schedules and visitor information.