Oldcastle Theatre Company

Up Next

Family Affair—Cabaret served up family-style

Family affair

Jan. 26th – 7:30pm

Tickets are $10 cash at the door. Adults age 16 and up.
Not suitable for children.

Jennifer Jasper, Kate Whitehall and the Better Bennington Corporation with co-sponsor Oldcastle Theatre presents: Family Affair—Cabaret served up family-style

Love them or hate them…they’re your family. Storytellers, dancers, writers, musicians and artists share their hilarious, twisted and ultimately relatable familial skeletons in their own unique way. During the show we pass a bucket to raise money for a local organization that helps our community “family.” This performance benefits The Kitchen Cupboard in Bennington. A portion of the ticket sales also goes into the bucket.

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Join us Across the Pond – 10 Day Theatre Trip to London

March 7th to the 17th, 2019

The Trip Includes

  • Roundtrip airfare from Boston (Logan) to London Heathrow.
  • Airport transfers to and from Heathrow and the hotel by private motor coach.
  • Escorted 1⁄2 day bus tour of London with Select Travel’s guide (including a stop at Westminster Abbey). This is to fill time before we can check in at the hotel.
  • Full English breakfast every day.
  • 9 nights’ hotel accommodation at the Copthorne Tara Hotel (just off Kensington High Street).
  • Welcome dinner.
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Coming Soon

Family Drama Course

Sally Sugarman
Tues. Jan. 8, 2019 through Feb. 26th – 7 to 9 p.m.

Sally Sugarman, a long time professor at Bennington College, is joining with the Oldcastle Theatre Company to present a class entitled “The American Family Drama” for eight weekly sessions from Tuesday January 8, 2019 through February 26th from 7 to 9 p.m. at Oldcastle Theatre, 331 Main Street in Bennington.

Ms. Sugarman taught a similar class with other faculty members of Bennington College. The idea of the new class came about during a discussion with Oldcastle’s Producing Artistic Director, Eric Peterson. Ms. Sugarman and Peterson were talking about the breath and diversity of great American plays centered on the family. Several of the plays discussed during that conversation are included in the upcoming course.

Acting 101 Is Back

Acting 101 - January 7th
Starting January 7th

This class will meet for 8 weeks on Monday nights 7 – 9 pm. Instructor Christine Decker, actor and Director of Education at Oldcastle, will work students through scenes, monologues, and exercises, to culminate in a showcase of performances. Open to every level of experience, from the seasoned to the brand new.
Call Oldcastle at 802-447-0564 to reserve your spot, as space is limited.

Conversations From The Green Room


A five play theatrical season is a journey with ever changing scenery and new traveling companions. The trip is occasionally treacherous, often amusing, challenging, tension-filled, and ultimately, one hopes, gratifying. Our 47th excursion began during the Revolutionary War in the Berkshires, traveled to England and back again, then to the American south of the Civil War; before leaping to the early 21st century with a comedy featuring 20th century music by Cole Porter.