Professional Live Theatre in an Intimate New Performance Space.

331 Main Street Bennington, Vermont

Past Performances

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


“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.

Telly Halkias ‘Still, it’s early June. The crowds aren’t quite out yet. But if you love the stage and love comedy and love excellent acting and directing, then beat feet to Bennington and Oldcastle, and prime yourself for entering the theatre of the absurd.”

Peter Bergman~Berkshire Bright Focus This group of actors takes your breath away while you laugh and laugh and laugh and glory in their quick timing, their many character and costume changes and their fabulous accents.”  “This is my third production of this show and it is by far the best I’ve seen. The company and the company that keeps them really deliver the laughs in this outing and it’s one good reason to start your car and head to the biggest little theater in the smallest big city in southern Vermont before its too late. You don’t want to miss this one.” Read Peter Bergman’s full review here


Big River, The Adventures of Huckleberry Finn


Music & Lyrics by Roger Miller

Book by William Hauptman


J. Peter Bergman of Berkshire Bright Focus, says ” In the words of Roger Miller, with a bow to Mark Twain, if you’re waitin’ for the sun to shine, you’ll find plenty of it at Oldcastle’s production of BIG RIVER.”

Jeff Borak of The Berkshire Eagle, “Huck, especially as played by Anthony Ingargiola with such fresh appeal, openness and ingenuousness, ..”

“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.

..” in light of recent tragic events, everyone should be clamoring to bring their entire family, children and all, to see this musical.” Telly Halkias of The Bennington Banner

Tickets Available

Hear from some of the cast and the Musical Director

The City of Conversation

by Anthony Giardina

“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.”

Tickets Available

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

by John Morogiello


“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


“so chilling and honest that we forget we’re watching a play and just for an instant believe we are peering through a time-warp into the actual confrontation.” J Peter Bergman~” Berkshire Bright Focus



“Oldcastle’s “Tramp” – great story, exceptional acting” Telly Halkias ~ Bennington Banner


Copy of DavidJoseph

Tickets Available


See what the actors have to say about The Consul, The Tramp & America’s Sweetheart



David Joseph as Charlie Chaplin







Elizabeth Aspenlieder and David Joseph







Lori Vega and Paul Romero


The Ride Down Mt. Morgan

by Arthur Miller

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.

Tickets Available

Performances from 2015

The Lion in Winter


Black Comedy



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Time Stands Still

Talley’s Folly

Time Stands Still by Donald Margulies

Pulitzer Prize winner Donald Margulies has written a powerfully contemporary , searing story of an heroic female journalist wounded covering the war in Iraq.  Can you be a dispassionate, uninvolved observer of horrific events, recording them for posterity and still keep a sense of right and wrong? That is just one of the intriguing questions in this smart, timely, stylish and compelling play.

June 5 – June 21, 2015


Marianna Bassham – Sarah

Jason Guy – James

Richard Howe – Richard

Kristin Parker – Mandy


Black Comedy By Peter Shaffer

In one hilarious act, the action supposedly in the dark is illuminated, when the lights are to be on, the stage is dark. Lovesick and desperate, Brindsley a young sculptor has embellished his apartment with furniture and objects d’arte “borrowed” from the absent antique dealer next door hoping to impress his fiancee’s pompous father and a wealthy art dealer. The neighbor returns just as a blown fuse plunges the apartment into total darkness and Brindsley is revealed teetering on a the verge of a very ripe farce. Unexpected guests, aging spinsters, errant phone cords, and other snares impede his increasingly frantic efforts to return the  stolen items. Shaffer has written a non-stop laugh riot!

“One of the funniest and most brilliant plays ”
London Times
“Laughter mounts steadily”
New York Times”

August 21 – September 6, 2015


Jim Staudt'

Jim Staudt-Brindsley Miller

Colonel Melkett

Gary Poe-Colonel Melkett

Richard Howe -Schuppanzigh

Richard Howe -Schuppanzigh

Georg Bamberger

Peter Langstaff-Harold Gorringe

Christine Decker-Miss Furnival

Christine Decker-Miss Furnival

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Ana Anderson as Clea

Amanda Garcia

Amanda Garcia

Dan Silver

Dan Silver


By Alan Jay Lerner & Frederick Lowe

Based on Pygmalion by George Bernard Shaw

331 Main Street,

My Fair Lady

The most loverly love story the world has ever taken to heart in the greatest musical of all-time. Glorious songs, memorable characters and enchanting romance all in a miraculous, wise, witty and winning show that is not to be missed.



Tennessee Williams – Playwright

331 Main Street,

Cat On A Hot Tin Roof - Oldcastle Theatre Co.

A brilliant playwright at his very best this play features some of Williams’ most memorable characters. Sexy Cat desperate to regain the love of her tortured husband, Brick; and Big Daddy a towering man of colossal appetites fighting for his life.



Playwrights: Anthony Marro and Eric Peterson

331 Main Street,

Southern Vermont’s Greatest Generation helped save the world for democracy during World War II. Based on interviews done by the Bennington Historical Society this is their story.


Play Date

Playwright: John Morogiello

Play Date - Oldcastle Theatre Co

331 Main Street,

It’s the parents who are naughty in this hilarious mix of winning and losing friendships, adultery, politics and scheming to get one up on their neighbors while in the midst of their children’s play date. By the author of ENGAGING SHAW a play that Oldcastle premiered that has now been produced around the world.



Playwright: John Patrick Shanley

331 Main Street,

Doubt - Oldcastle Theatre Company, Bennington Vermont

Hailed by critics and audiences as a brilliant, powerful drama about a nun who suspects a young priest of improper relations with a student; this winner of the Pulitzer and Tony Awards, the play is an eloquent and provocative investigation of truth and consequences.


4000 MILES

Playwright: Amy Herzog

4000 Miles - Oldcastle Theatre Company, Bennington Vermont

331 Main Street,

Winner of the Obie Award for Best Play and a finalist for the Pulitzer, this warm-hearted play by one of our most acclaimed young playwrights, tells the story of a 21 year old, after the loss of a loved one seeks the solace of his feisty 91 year old grandmother. Critics called it “funny, moving, altogether wonderful” and a “well-observed gem.”