While not in New York proper, the Berkshires are an essential part of live music for those in Eastern New York and beyond. Intersecting multiple state lines, these highlands boast a vibrant community of artists and art alike- drawing both locals and those from beyond the mountains into its captivating live performance scene. From grandiose theaters to intimate speakeasies, the Berkshires offer a venue fit for every event and occasion.
Be sure to check out our look at the venues of Western New York, Hudson Valley, North Country, the Capital Region, Central New York, and Southern Tier as well.
Berkshire Theatre Group (Pittsfield)
Formed by the merging of the Berkshire Theatre Festival and The Colonial Theatre, two of the county’s oldest cultural organizations, the Berkshire Theatre Group has a long history of bringing live performance to its community. Boasting a catalog of performances dating back to 1928 and an ever-expanding repertoire of both time-honored classics and works from new and emerging artists, the performances of the Berkshire Theatre Group span four stages- The Colonial Theatre, The Unicorn Theatre, The Fitzpatrick Main Stage, and The Garage, each with their own unique personality and purpose.
Address: 6 East St, Stockbridge, MA 01262 (The Unicorn Theatre, The Fitzpatrick Main Stage)
Address: 111 South St, Pittsfield, MA 01201 (The Colonial Theatre, The Garage)
Chester Theatre Company (Chester)
Known for their contemporary productions, Chester Theatre Company hosts a series of shows made and performed by those in the community every summer. In addition to their own works, the Company hosts talkbacks, cast conversations, and panel discussions.
Address: 15 Middlefield Rd, Chester, MA 01011
Great Barrington Public Theater (Barrington)
Built completely upon and around the talents and works of those local to the Berkshires and beyond, The Great Barrington Public Theater performs in the Daniel Arts Center of Bard College at Simon’s Rock, either on the 300 seat mainstage McConnell Theater with orchestral and balcony seating or the 100 seat Liebowitz Black Box Theater.
Address: 84 Alford Road, Great Barrington, MA 01230
Mac-Haydn Theatre (Chatham, NY)
The Mac-Haydn Theatre has been producing musical theater performances for the area for over fifty years now- bringing the founding wish to spread professional musical theater beyond Broadway to fruition. Each performance comes to life on their 350 seat theatre-in-the-round stage, creating an engaging and intimate audience experience. Shows run each season between Memorial Day weekend and Labor Day Weekend.
Address: 1925 NY-203, Chatham, NY 12037
Mahaiwe Performing Arts Center (Great Barrington)
Constructed in 1904 and opened in 1905, the Mahaiwe Performing Arts Center has acted as a community cornerstone for live performance, film, and cultural events since its inception. Boasting theater seats just under 700, year-round arts programming, and a range of events from entertainment to education, the Mahaiwe is the centerpiece to the town’s vibrant art scene.
Address: 14 Castle Street, Great Barrington, MA 01230
PS21 (Chatham)
An abbreviation for Performance Space 21, this black box theater sits atop a mountain. PS21 is home to contemporary dance, theatre, and music that hosts cutting edge artists from across the globe. Like many performances at this venue that invite the audience to interact- oftentimes more workshop than production- visitors can explore the fields and view of the Hudson below.
Address: 2980 Route 66, Chatham, NY 12037
Shakespeare & Company (Lenox)
Founded in 1978, Shakespeare & Company boasts a wide range of theaters to fit each production’s needs. With tried and true Shakespearean classics, reimagined pieces, and newly debuted shows, Shakespeare & Company utilizes every seat of their 540-seat open air Arthur S. Waldstein Amphitheatre, 400-seat scaffold-and-canvas inspired Tina Packer Playhouse, intimate five row Elayne P. Bernstein Theatre, Elizabethan inspired 280-seat outdoor Roman Garden Theatre, and the 250-seat Rose Footprint Theatre, a reconstruction of the first level of Shakespeare’s first London theater.
Address: 70 Kemble St, Lenox, MA 01240
Tanglewood (Stockbridge)
With a rich history of live music and musical education, an open-air venue with both indoor seating and an outer lawn that provides a variety of listening experiences, and a star studded performance archive that ranges from Ella Fitzgerald to Dolly Parton, it’s no wonder Tanglewood has been consistently voted a fan favorite concert venue. In addition to individual performances, Tanglewood houses the Popular Artists Series festival, the Boston Pops, and the Boston Symphony Orchestra’s training academy.
Address: 297 West St, Lenox, MA 01240
The Egremont Barn (South Egremont)
An informal, cozy venue nestled in an old barn at the Egremont Village Inn, The Egremont Barn offers a more casual audience experience complete with pub style comfort foods and a stage boasting little more than a piano. The venue’s charm shines through in its community built around the year-round program of singer-songwriters, theater companies, open mics, and musical acts across genres.
Address: 17 Main Street, South Egremont, MA 01258
The Lion’s Den (Stockbridge)
A small speakeasy style venue tucked beneath the Red Lion Inn, The Lion’s Den offers an intimate musical experience with a timeless atmosphere. Thursday through Saturday evenings feature folk, rock, and blues acts from their Den Sessions, and Sunday evenings are the host to their Jazz series.
Address: The Red Lion Inn, 30 Main St, Stockbridge MA 01262
Williamstown Theatre Festival (Williamstown)
A Tony Award-winning theater, The Williamstown Theatre Festival is a resident summer theatre on Williams College’s campus that hosts a yearly season of shows and community immersive theatre programs year-round.
1000 Main Street, Williamstown, MA 01267
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