A Creative Heartbeat in Downtown Bennington

Learn more about our story and mission.

Establishment & Evolution

Welcome to Bennington Theater—where national talent, local stories, and unforgettable nights come together on one intimate stage.

Bennington Theater is more than a stage—it’s a performance venue and launching pad for regional culture, artistic innovation, and unforgettable live performance. With over 100 events in 2024, we bring a bold range of talent to downtown Bennington—from national touring acts to community-led productions.

We serve audiences from Vermont, New York, and Massachusetts, and anchor Bennington’s growing cultural economy.

From Oldcastle to Bennington Theater

Sign for Oldcastle Theatre hanging on brick building in Bennington Vermont

Our roots stretch back to Oldcastle Theatre Company, founded in 1972 by New York actors committed to professional theater in Southern Vermont. After decades of acclaimed productions and community presence, the company moved into a downtown black box theater in 2019 and reintroduced itself as the Bennington Performing Arts Center.

In 2022, we became Bennington Theater: a new name for an expanded mission—bringing world-class artists, diverse entertainment, and fresh energy to the region.

What We’ve Built

A collage of scenes from a theatrical performance, featuring actors in period costumes, musicians, singers, dancers, and a director or host on stage, with various backdrops and stage settings at Bennington Theater

Since our relaunch, we’ve proudly led the way in redefining the local arts scene:

  • National Touring Talent
    Introducing the region to critically acclaimed musicians, comics, and theater companies from across the U.S.

  • Live Comedy Pioneers
    The first venue in the area to consistently program stand-up and improv with sold-out results

  • Live Music, Elevated
    With our new state-of-the-art sound system, we’ve amplified what’s possible on our intimate stage—attracting bigger acts and unforgettable concerts

  • Community Theater, Reimagined
    Collaborating with regional artists, educators, and volunteers to produce high-quality local productions with a fresh, inclusive spirit

  • New Works Series
    Featuring staged readings and developmental performances of never-before-produced plays

  • Engaging Events
    House-produced series like Trivia Night Live (hosted by Jim Thatch) and Wine & Improv invite everyone to participate—not just watch

Regional Partners, Local Impact

An audience gathered in a theater watching Peter Antoniou on stage at Bennington Theater

We are proud members of:

  • Better Bennington Corporation

  • Southwestern Vermont Chamber of Commerce

And we actively partner with:

  • Local businesses

  • Schools and education programs

  • Community nonprofits

  • Regional arts organizations

Bennington Theater helps drive foot traffic, tourism, and creative energy into the heart of downtown—one performance at a time.

A man on stage holding a microphone, gesturing with his right hand, with colorful stage lights behind him.

Bennington County Regional Commission.

“Bennington Theater is critical component of the revitalization of downtown Bennington. We think it does nothing but add to and enhance all of the other redevelopment efforts.”

John Shannahan, former executive director, Better Bennington Corp.

“Every downtown organization would kill to have live theater on Main Street.”

Over 100 Events, One Stage

Local theatre Info

We’re on track to present over 100 events all-year-round, across:

  • Theater (professional, community, and youth)

  • Touring music acts and regional bands

  • Live comedy, improv, and original programming

  • Special events, readings, and pop-ups

  • Engaging house series and community experiences

Whether you’re here for a performance or planning your own event, Bennington Theater is your stage in the heart of it all.