BENNINGTON – The transformation of any performing arts organization can be rife with both pitfalls and successes along the way. But as far as the recently rebranded and reimagined Bennington Theater is concerned, its post-pandemic evolution from Oldcastle Theatre Company to the Bennington Performing Arts Center to its current iteration has been steady.
Recently, Bennington Theater executive director Kaiya Kirk had a chance to sit down with Vermont News and Media Correspondent Telly Halkias to answer a few question about the organization and also offer up a slate of events scheduled so far for 2026.
TH: What is the overall vision of Bennington Theater in terms of evolving into this multi-event type of organization?
KK: It’s about becoming a true cultural hub rather than a single-lane theater organization. Historically, many people associate a theater with one type of programming, plays or a fixed season model, but that no longer reflects how communities engage with the arts or how audiences want to experience live events today.
By embracing a multi-event model, we can offer theater, comedy, music, film, lectures, workshops, family programming, community gatherings, and experimental work under one roof. This flexibility allows us to serve a broader cross-section of the community while still maintaining artistic excellence.
It’s also about sustainability. A diversified programming model helps stabilize revenue, keeps the building active year-round, and ensures the space feels alive and relevant. We want Bennington Theater to be the place people instinctively think of when they ask, “What’s happening in town tonight?”
TH: What are the biggest challenges you have faced in your year as Executive Director?
KK: First, I will say that I feel incredibly fortunate. I love theater, I love the performing arts, and I love this building, so when the choice was to step up or potentially lose it, it was a no-brainer.
Yes, there have been a lot of challenges. Or maybe more accurately, learning opportunities. I am fortunate to have strong mentors and community leaders to lean on.
There is also the challenge of redefining expectations. As we have rebranded and expanded beyond a traditional producing theater model, a big part of my job has been clearly communicating who we are now and where we are headed. That takes time, consistency, and trust-building, but it is also one of the most rewarding parts of the work.
TH: Theater still remains very popular in this area. How does the community theatre company play into the annual schedule, and why is it important aside from more regularly occurring events and programming?
KK: Bennington Theater simply would not exist without the legacy and impact of Oldcastle Theatre Company. That is who we are. Producing work in-house is not just something we do. It is a core part of our identity and infrastructure.
Anyone who has taken a tour of the building, and I always encourage people to, will see that most of our basement exists specifically to support production: a fully outfitted scene shop, costume shop, and prop room. What we call our green room for touring artists is actually a beautiful rehearsal space with a wall-to-wall mirror.
These spaces were built through the blood, sweat, and tears of many people who created and championed Oldcastle Theatre Company over decades.
Community theatre serves a crucial function. It engages local talent, which frankly is incredible, keeps the building fluent in the rhythm of mounting productions, and helps us refine a model that is both time- and cost-efficient so we can ultimately bring more theater here.
TH: What do you want audiences to walk away with after attending any event at Bennington Theater?
KK: Above all, I want audiences to leave feeling connected: connected to the art, to one another, and to the community they live in. Whether they have laughed, reflected, learned something new, or simply had a great night out, I want it to feel like the experience mattered.
I also want people to feel welcome and surprised. Bennington Theater should feel accessible without being predictable, intimate without being limiting. Ideally, audiences leave thinking, “I didn’t expect that. I thought I would have to drive to Albany for something like this. And I want to come back.”
This work is deeply collaborative. The success of Bennington Theater is not driven by one person. It is the result of staff, board members, artists, volunteers, donors, and audiences who believe that arts and culture are essential to a healthy community.
As we look toward 2026 and beyond, the most exciting thing is not just what is on the calendar. It is the growing sense of shared ownership. Bennington Theater belongs to this town, and every season is an opportunity to strengthen that relationship.
Bennington Theater offerings for 2026
Trivia Night Live with Jim Thatch – every second Thursday
Where knowledge meets laughter in a friendly, competitive atmosphere. Match wits with our trivia-master Jim Thatch
Wine & Improv with Stephanie Phelan – every third Thursday
A night of hilarious improvisation where the only script is spontaneity! An interactive evening of improv games led by seasoned performer and director Stephanie Phelan.
New Works Series – readings of unproduced plays – likely bi-monthly
The New Works Series features staged readings of plays in progress, and is in its 3rd season this year at Bennington Theater. Local actors perform original new plays, scripts in hand, after only 6 hours of rehearsal. The plays may be staged or simply read aloud.
Live Music – once per month
Nationally Touring bands/artists. Experience our state-of-the-art sound system in the perfect listening room setting.
Live Comedy – once per month
Featuring many nationally touring comedians. From SNL or AGT or Comedy Central straight to Bennington Theater. High caliber comedic talent right in the heart of Bennington.
Large Community Theater Production – once every quarter
VAE Basement Music Series – the full series
Vintage Hollywood Movie Series – every Friday in a chosen month once schedule
The classics the way they were meant to be seen. And, yes, there is popcorn.
Gypsy Layne’s final-ever performance – February
After 16 glorious years, Gypsy Layne is hanging up the G-string… but first, one last showstopper at Bennington Theater this Valentine’s weekend.
Bennington Theater is located in downtown at 331 Main St. For a schedule of upcoming programs and events and e-ticketing: visit tickets.benningtontheater.org or call 802-500-5500
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‘ Some details of this article were extracted from the following source www.benningtonbanner.com ’
