Kids Concerts with Terry A La Berry and Friends

Colonial Theatre 111 South St, Pittsfield

Returning by popular demand, join us for an unforgettable musical experience with Terry A La Berry and Friends in The Garage at The Colonial Theatre! Terry A La Berry, renowned […]

Free

Jack Waldheim

Balderdash Cellars 81 State Road, Richmond

No further information available.

Free

TLI Presents: BSO Holiday Brass

Tanglewood 297 West Street, Lenox

Studio E, Linde Center for Music and Learning, Lenox/Stockbridge, MA The newest holiday tradition in the Berkshires! Join members of the BSO’s brass section for a program of cheerful and […]

$56.99

Joe James

Berkshire Mountain Distillers 356 South Main Street, Sheffield

3-5pm, Live Music Saturdays, Come have a cocktail or tasting flight while listening to some of the region's best local musicians. No charge.

Free

Paul Winter Consort Winter Solstice Celebration

St. James Place 352 Main St, Great Barrington

Seven-time Grammy®-winning saxophonist Paul Winter, with the Paul Winter Consort, returns to celebrate the Winter Solstice on Saturday, December 20 at 3:00pm at Saint James Place. A uniquely intimate solstice […]

$69

Children’s Holiday Sing Along with John and Ann Marie Farrell

Becket Arts Center 7 Brooker Hill Rd, Becket

Get ready to sing, laugh and learn! 🎶 Join renowned children's performers John and Ann Marie Farrell for a special Children's Holiday Singalong at the Becket Arts Center on December […]

Free

Berkshire Lyric Presents: The Most Wonderful Time of the Year

First Congregational Church of Stockbridge 4 Main St, Stockbridge

Berkshire Lyric presents The Most Wonderful Time of the Year, on Saturday December 20. The holiday choral program will take place at 4:00 at the Stockbridge Congregational Church on Main […]

$20

Holiday Sing Along

Becket Arts Center 7 Brooker Hill Rd, Becket

Get ready to sing your heart out! Join us for our beloved annual Holiday Singalong. We'll provide the songbooks, and you can bring your voice, your instrument, or just your […]

Free

Celtic Christmas with Kilashandra!

portaVia 645 Main St, Dalton

A Celtic Christmas Celebration with Award Winning Artists…Kilashandra! You’ve seen them at our “Shamrock for a Day” St Pats Parties…Don’t Miss This, Reserve your Table Today!!!

Free

What to wear

MASS MoCA 1040 Mass MoCA Way, North Adams

The centerpiece of the PROTOTYPE 2026 festival will be the New York premiere of What to wear, a comedic, post-rock opera by composer Michael Gordon and the late downtown theater […]

$44 – $74

Studio 9 Present Misty Blues Live

Studio 9 18 Veazie St, North Adams

Join us for a night of amazing blues music with the Misty Blues Band. 2019 International Blues Challenge finalist, Misty Blues, is fronted by lead singer/band founder Gina Coleman. The […]

$20

The Slackers

Route 8 Pub 3235 Main St, Becket

Great Food Great Music Great People

Free

Paul Winter Consort Winter Solstice Celebration

St. James Place 352 Main St, Great Barrington

Tickets on Sale October 9 at 9am! Seven-time Grammy®-winning saxophonist Paul Winter, with the Paul Winter Consort, returns to celebrate the Winter Solstice on Saturday, December 20 at 7:00pm at […]

$69

Chuck Clough

Antimony Brewing 55 Pittsfield Rd, Lenox

No further information available.

Free

Andy Wrba & Friends

The Lion's Den 30 Main Street, Stockbridge

December Den Sessions. Spirits & Live Music for All, 7 - 10 PM

$10

Holiday Spectravaganza

Barrington Hall Stockbridge Road, Great Barrington

The Berkshires’ most joyfully chaotic holiday tradition is coming to Barrington Hall. For the first time ever, the beloved Holiday Spectravaganza lands on our stage — hosted by comedian and […]

$17

The Wizards of Winter

Colonial Theatre 111 South St, Pittsfield

Back by Popular Demand! Celebrate the season with a spectacular holiday rock opera that will leave you filled with wonder and cheer! Returning for their third year at The Colonial […]

$59

An Evening with Ellis Paul

Buttonball Barn 17 Main Street, South Egremont

Ellis Paul doesn’t just write songs; he’s a guitar-carrying reporter who covers the human condition and details the hopes, loves, losses of those he observes, turning their stories into luminous […]

$35

John Pizzarelli Trio: Tony Bennett – The Art of Excellence

Mahaiwe 14 Castle St, Great Barrington

Grammy Award-winning producer and guitarist extraordinaire, John Pizzarelli salutes the legendary Tony Bennett celebrating over 60 years of unparalleled artistry. From Bennett’s ’50s pop hits like “Because of You” and […]

$44 – $89