In the heart of Downtown Bennington, the Bennington Theater, formerly known as Oldcastle Theater, is set to captivate audiences once again with its highly anticipated 2024-2025 season. Located at 331 Main Street, this beloved cultural hub is committed to enriching the community through the transformative power of live performance, offering a diverse range of shows year-round.
Welcome To Our 52nd Season!
This season promises a dynamic array of 30 performances through December, with more lined up for 2025.
The ever-popular Comedy Series returns, bringing over 20 nationally touring comedians to the stage. Kicking off on September 21 is Graham Kay, fresh from appearances on The Tonight Show and The Late Show. Returning favorites include Michael Palascak (October 26) and Jon Rudnitski (November 16), who wowed Bennington audiences last year with sold-out shows.
For the first time, Tom Thakkar (October 5), Ryan O’Flanagan (October 12), Taylor Williamson (November 2), and Tom Cotter (November 30) will join the lineup.
A Season of Music and Magic
Bennington Theater‘s Music Series with the genre-bending group Gangstagrass, known for their unique fusion of bluegrass and hip-hop, performs on September 19 in a special members-only event. Their innovative sound, famously featured in the TV show Justified, is sure to leave a lasting impression.
On September 29, TAKE 3 will dazzle with their “Bach Meets Rock” fusion, blending classical and contemporary styles in a performance full of energy and passion.
Swing fans won’t want to miss PHAT CAT, an 11-piece swing band from Hollywood, who will have the town dancing on Main Street on November 14.
Theater and Film
This season isn’t just about music and comedy—there’s plenty of theater to enjoy as well. The Halloween favorite Whispering Bones returns with spooky stories and spine-tingling laughter. Plus, the theater will be launching a new film series, starting with an exciting film festival.
Engaging Events for All
The 2024 season will feature a continuation of the popular children’s shows and an exciting new dance series for all ages.
In addition to performances, Bennington Theater brings back its popular Trivia Night Live! hosted by Jim Thatch. Each month, individuals and teams can test their wits across a variety of topics, from movies to science.
Stephanie Phelan also returns with her Wine and Improv event, where participants are invited to unleash their creativity through live theater games. No experience is required—just a sense of humor and a willingness to have fun.
New Leadership and Fresh Works
This season marks a new chapter with the arrival of co-artistic directors David Dubov-Flinn and John Lugar. Together, they will lead the charge in producing an exciting season of theater, starting with Scrooge in Rouge, a cheeky, campy twist on A Christmas Carol.
Suzanne Wessler heads up the New Works Series, a program dedicated to showcasing never-before-produced plays. This fall, the program will feature Rhinestone Cowboy and The AI at Delphi, giving audiences the chance to engage directly with playwrights through talkbacks and feedback sessions.
For more details and tickets, visit BenningtonTheater.org or call (802) 500-5500.
