Berkshires Music & Theater: classical, comedy, rock & roll…we have it all!

No Berkshires vacation is complete without enjoying Berkshires Music or a trip to the theater. The Berkshires are home to some of the best theatrical performances in New England. The Inn at Stockbridge is conveniently located close to a variety of events and live performances, including Tanglewood, home of the Boston Symphony Orchestra, and the historic Jacob’s Pillow Dance Festival. But there are so many other wonderful places to see a show, listen to music, and enjoy live performances.

Best of Berkshires Music & Theater

Shakespeare & Company

Classic theater and new plays from late June – August. Founded in 1978, Shakespeare and Company participants aspire to create a theatre of unprecedented excellence rooted in the classical ideals of inquiry, balance, and harmony; a company that performs as the Elizabethans did — in love with poetry, physical prowess, and the mysteries of the universe.


Berkshire Theatre Group

Music and theater year-round, 5 stages in Stockbridge and Pittsfield! Berkshire Theatre Group was created in 2010 by the merger of two of Berkshire County’s oldest cultural organizations, Berkshire Theatre Festival founded in 1928 in Stockbridge and The Colonial Theatre build in 1903 in Pittsfield. One of the largest and most exciting arts organizations in the area, BTG oversees the development, production and presentation of theatre, music and the performing arts on 5 stages.  The Berkshire Theater Festival is just down the road from us here in Stockbridge.

Berkshire Theatre Group

Barrington Stage Company

Music and theater year-round, 5 stages in Stockbridge and Pittsfield! Berkshire Theatre Group was created in Great theater in downtown Pittsfield, the summer season begins in May. Co-founded in 1995 by Artistic Director Julianne Boyd, Barrington Stage Company (BSC) is a not-for-profit professional theatre company in the Berkshires (MA), with a three-fold mission: to produce top-notch, compelling work; to develop new plays and musicals; and to find fresh, bold ways of bringing new audiences into the theatre, especially young people.


The Capitol Steps

Political Satire, June 29 through August 31 at Cranwell – Very popular with our guests! Hilarious political satire and song parodies returning to Cranwell this summer.  The Capitol Steps began as a group of Senate staffers who set out to satirize the very people and places that employed them.  Since they began in 1981, the Capitol Steps have recorded over 30 albums including their latest “Orange is the New Barack”.  They’ve also been featured on NBC, CBS, ABC, and PBS, and can be heard 4 times a year on National Public Radio stations nationwide during their “Politics Takes a Holiday” radio specials.


Mahaiwe Performing Arts Center

Year-round presenter of performing arts, film, educational, and family programs. In Great Barrington, Mahaiwe Performing Arts Center offers a wide variety of programs in dance, music, theatre, and opera in their newly restored theater. Dinner in Great Barrington followed by a show? Sounds fantastic!


Infinity Music Hall

Norfolk, CT.  A great line-up of popular artists!  About 40 minutes from the Inn. Built in 1883 in picturesque Norfolk, Connecticut, Infinity Music Hall is an intimate music, dining, and entertainment destination beyond compare.  Newly renovated, the historic building features its original proscenium stage and wood, as well as many other notable details.



A summer getaway to the Berkshires is not complete without a visit to Tanglewood, the summer home of the Boston Symphony Orchestra, and only 10 minutes from the Inn!


Jacob’s Pillow

Each summer the internationally-recognized Jacob’s Pillow Dance Festival delights visitors with routines featuring stunning choreography that tell elaborate stories through dance.

Jacobs Pillow