Professional Live Theatre in an Intimate New Performance Space.

331 Main Street Bennington, Vermont

2016 Season

Oldcastle Celebrates 45 Years of Live Theatre

Performance Times: Wednesday-Saturday · 7:30pm.

Matinees on Thursday and Sundays · 2pm- Saturday June 4 special matinee performance


The 39 Steps


adapted by Patrick Barlow

from the novel by John Buchan

from the movie of Alfred Hitchcock

Licensed by ITV Global Entertainment Ltd.

Original concept by Simon Corbie and Nobby Dimon


Opens June 3

Closes – June 19

“The 39 Steps” a long running Broadway comedy mixes a Hitchcock masterpiece with a juicy spy novel, adds a dash of Monty Python to create a fast-paced whodunit for everyone who loves the magic of theatre.   A two-time Tony and Drama Desk Award-winning treat is packed with nonstop laughs over 150 zany characters and an on-stage plane crash, handcuffs, missing fingers and some good old-fashioned romance!

In “39 Steps”, a man with a boring life meets a woman with a thick accent who says she’s a spy. When he takes her home, she is murdered. Soon a mysterious organization called “The 39 Steps” is hot on the man’s trail in a nationwide manhunt that climaxes in a death-defying finale! A riotous blend of virtuoso performances and wildly inventive stagecraft, “The 39 Steps” amounts to an unforgettable evening of pure pleasure

Buy Tickets Here

Meet the Cast of THE 39 STEPS

Natheadshot Natalie Wilder

1 6 15 peter-2 Peter Langstaff

Shea_Patrick_5A38_ret2 Patrick Ellison Shea

Jim Staudt' James Staudt

BIG RIVER, The Adventures of Huckleberry Finn

Music & Lyrics by Roger Miller

Book by William Hauptman

Opens – July 8

Closes – July 24–There will be one additional performance each week on Sunday evening. Bring the kids, and the grand-kids to this family show

Special Sunday Evening Performances for Big River Thursday & Sunday · 2pm

 “Big River, The Adventures of Huckleberry Finn” won seven Tony Awards including Best Musical and Seven Drama Desk Awards. The music and lyrics are by the beloved, funny and wise Grammy winning country crossover singer-songwriter, Roger Miller. Miller’s eleven Grammy winners and six Gold Records included such indelible hits as “King of the Road, Dang Me, England Swings, and One Dyin’ and a Buryin” astonished Broadway audiences with infectious melodies, his clever, amusing, heartfelt and touching lyrics and his deep understanding of the complexity and beauty of Mark Twain’s seminal novel. William Hauptman’s book beautifully captures Twain’s rollicking story that is simultaneously subversive, hilarious and tender.


The City of Conversation

by Anthony Giardina

Opens – August 5

Closes August 21

“The City of Conversation” premiered at Lincoln Center two years ago and is a play that is both timely and timeless. It opens in 1979 in Washington, D.C. when the Capital City was a place where people actually talked to each other; where adversaries fought it out on the Senate floor and then smoothed it out over drinks and hors d’oeuvres. But it was all about to change. In this play spanning 30 years and six presidential administrations, Hester Ferris throws Georgetown dinner parties that can change the course of Washington’s politics. But when her beloved son suddenly turns up with an ambitious Reaganite girlfriend and a shocking new conservative world view Hester must choose between preserving her family and defending the causes she’s spent her whole life fighting for. Anthony Giardina has written a play about politics in a family and family in politics. A searing new drama, “The City of Conversation” delves into the ever-changing tapestry of U.S. Government and the people who shape it off the senate floor. The Washington Post wrote: “The City of Conversation” achieves something that eludes many other plays about Washington; a savvy depiction of social skill as political art, in a city that is defined by political science…Giadina’s handiwork presents to the world one of the most fair-minded, even compassionate views of the partisan struggles of the city’s political classes you’re likely to encounter these day.”


The Consul, the Tramp & America’s Sweetheart~ World Premiere!

by John Morogiello

Opens Sept. 2

Closes – Sept. 18

“The Consul, the Tramp and America’s Sweetheart”  won first place in the 2015 Dayton Playhouse FutureFest and the 2015 Julie Harris Playwright Award Competition from the Beverly Hills Theatre Guild.  It was developed at New Jersey Rep, Luna Stage, and the Historic Elitch Gardens Theatre in Denver. Oldcastle Theatre has twice presented premieres of plays by Baltimore playwright John Morogiello. “Engaging Shaw” has been produced around the world and “Playdate” which Oldcastle premiered in 2014 is now being produced by regional theatres around the U.S.

The Consul, the Tramp & America’s Sweetheart’s  story,  concerns Charles Chaplin’s  film masterpiece, The Great Dictator and Germany’s attempts to prevent the movie from being made. The cast includes silent screen star, Mary Pickford, who became head of the studio she formed with Chaplin and Douglas Fairbanks, United Artists. The play contains some classic comedic pieces from Chaplin’s films and also concerns a young woman trying to make her way up the administrative ladder in Hollywood; as well as the Nazi Consul to the United States.

“This new play is funny, clever, has an interesting take on history, is play about women fighting to receive equal status and a test of commercial needs versus artistic freedom.”~Eric Peterson, Producing Artistic Director, Oldcastle Theatre Company


The Ride Down Mt. Morgan

by Arthur Miller

Opens – Oct. 7

Closes Oct. 23

Arthur Miller’s 100th birthday is being celebrated around the globe and Oldcastle Theatre will do its part to remind playgoers of the man’s genius with one of his last plays, “The Ride Down Mt. Morgan.” The New York Times wrote: “Any new play by Arthur Miller is an important event in American culture. One as theatrically bold and intellectually subtle as “The Ride Down Mt. Morgan” is a reason to shout for joy.”  The play concerns Lyman Felt a poet turned insurance tycoon in his fifties. Driving down Mt. Morgan in the snow he crashes his car and is taken to an upstate hospital. Summoned to his bedside are his daughter and his two wives:  Theo the older WASP-ish woman whom he married decades earlier and Leah, the young Jewish businesswoman who had been Lyman’s lover and insisted on becoming his wife. Now Lyman’s past, and his appetites, have caught up with him.   The play was first presented in London and then became a success, first at the New York Shakespeare Festival’s Public Theatre and then on Broadway starring Patrick Stewart. It is a towering role in a play filled with juicy parts for talented actors.

View our past performances