As we step into the second week of December, the holiday music season is in full stride. Out of the 49 shows happening across Berkshires County, 13 are holiday-themed, showcasing a variety of genres. Beyond the festive offerings, there’s an eclectic mix of classical, jazz, rock, folk, country, bluegrass, and old-time music—a rich tapestry of sounds to celebrate. Below are some highlights for the week ahead, followed by our comprehensive show rundown.
Holiday
With 13 holiday performances in the county this week, we decided to highlight these for our readers looking to boost their holiday spirit. These performances cross many musical genres.
The festivities start Thursday night with Tipsy Carol McBoozle’s Holiday Sing-Along at The Foundry in West Stockbridge. Tipsy’s sing-along performances always draw a crowd and will surely make you laugh and sing. Friday night, you’ll find An Evening of Holiday Jazz with Tim Jones in the Garage at the Colonial Theatre in Pittsfield. Berkshire Theatre Group alum Tim Jones will be joined by Jon Suters, Ben Kohn, and Conor Meehan, who will create an unforgettable night of holiday standards in a cozy, close-up setting. Also on Friday night, you’ll find Love’s Pure Light at St. Mark’s Church in Pittsfield. The Berkshire Lyric Chorus (pictured above) will be joined by their young women’s ensemble and children’s chorus to perform traditional and contemporary a cappella carols by Warlock, Pärt, Bruckner, Brahms, and others. The program repeats again on Sunday afternoon at St. James Place in Great Barrington.
Saturday afternoon, you’ll find the Stockbridge Festival Chorus in Concert at the First Congregational Church of Stockbridge. They will perform two pieces by Ralph Vaughan Williams, plus anthems by David Anderegg, Philip Stopford, and Bob Chilcott. Saturday night at the Tanglewood Linde Center, you can enjoy TLI Presents: BSO Holiday Brass, a festive and engaging family-friendly concert featuring members of the BSO’s brass section. The performance repeats on Sunday afternoon. Also on Saturday evening, you’ll find Vocalis Youth Choir: Songs of the Season at St. James Place in Great Barrington. The program repeats Sunday afternoon at The Southfield Church. For something a bit different, head on over to The Egremont Barn for The Holiday Spectravaganza! (And Jenny’s Birthday). We’ve attended this fun night for the past two years and came away with a deep sense of community and renewed holiday spirit.
On Sunday afternoon, you’ll find Yule for Fuel 2024 at the Zion Lutheran Church in Pittsfield, where the Berkshire Concert Choir, Zion Lutheran Church’s Bell Choir, and the Berkshire Hillsmen barbershop chorus raise funds for the Pittsfield Area Council of Congregations Fuel Fund. Or for some holiday cabaret, you can make your way to Ventfort Hall in Lenox for Naughty or Nice: Songs of the Season Holiday Cabaret featuring vocalist Sherri James Buxton and accompanist Bob Shepherd. Finally, you can enjoy a tasty beverage while listening to the Berkshire Concert Choir Community Sing at Hot Plate Brewing in Pittsfield.
Classical and Opera
In addition to several of the holiday performances above, we have six purely classical or opera performances this week. Thursday evening, you’ll find the Winter Concert at Bard College at Simon’s Rock in Great Barrington, where the Simon’s Rock Chamber Orchestra performs music by Vivaldi, Mozart, Haydn, Elgar, Dvorak, and Purcell.
Saturday afternoon, the whole family can enjoy the Aston Magna Family Day and Concert at St. James Place in Great Barrington, featuring a live interactive performance of Capriccio Stravagante by Carlo Farina. There will also be an instrument “petting zoo” for children. In the evening at Williams College, you’ll find the winter concert of the Northern Berkshire Chorale performing Regina Coeli K108 of W.A. Mozart and Requiem Mass of Jose Mauricio Nunes-Garcia with a full orchestra and soloists. At the Clark Art Institute in Williamstown, you can enjoy an evening of exceptional chamber music at the Williams College Chamber Music Gala. Back at the Clark on Sunday afternoon, you’ll find the Performing Artists in Residence Concert, where works by Mozart and Dohnányi will be performed. Also on Sunday afternoon, you can enjoy Close Encounters With Music: Vivace Chamber Orchestra – Tchaikovsky, Grieg, Britten, Boccherini, Barber at the Mahaiwe in Great Barrington.
Jazz
We have six jazz performances this week besides the one listed under our holiday section. Wednesday evening, the Kris Allen Trio performs at The Lion’s Den in Stockbridge. Thursday, The Lucky Three are at the Ostrich Room at Apple Tree Inn in Lenox.
Friday evening, you can catch the Fall 2024 Jazz Concert at Bard College at Simon’s Rock in Great Barrington, where the Simon’s Rock Jazz Ensemble, directed by faculty member John Myers, will perform a variety of beautiful standards by the great jazz masters. Saturday night, you’ll find the Luke Franco Trio at the Ostrich Room at Apple Tree Inn. Sunday midday, catch the Jazz Brunch with Limited Release Trio at Race Brook Lodge in Sheffield. On Sunday night, you’ll find Michael Junkins and Friends at The Lion’s Den. This week, Michael features Eric Loffswold on saxophone.
Popular (Rock, Pop, Folk, Blues, etc.)
The popular music category dominates our calendar this week, with over 20 performances. We can’t highlight them all, but we will mention a few (see our calendar or show rundown below for all the performances).
The music starts Monday with Nashville-based James Hatem and Miwi La Lupa at Methuselah in Pittsfield. Thursday night, Music in the Berkshires Featured Musician Clare Maloney and The Great Adventure returns to The Egremont Barn. At The Stationery Factory in Dalton, catch the talent of the future with Calliope Cafe.
Friday night, Railway Concerts Presents: Vance Gilbert at Studio 9 in North Adams. It’s a great opportunity to hear this contemporary folk musician in the beautiful listening room at Studio 9. Fans of the Grateful Dead won’t want to miss Dead Man’s Waltz plays Jerry Garcia Band at The Egremont Barn. Diva & The Dirty Boys are back at The Lion’s Den in Stockbridge, while Mr. Doubtfire performs at Firefly Gastropub in Lenox. Down at Race Brook Lodge in Sheffield, you can see Shinbone Alley with Bonnie Milner & Deirdre Murtha performing traditional and old-time music.
Saturday night, local folk-rocker Johnny Irion performs at The Lion’s Den. Fans of Judas Priest won’t want to miss The Priest – A Judas Priest Tribute at The Stationery Factory, while country and bluegrass cover band Skeeter Creek performs at Proprietor’s Lodge in Pittsfield.
Sunday morning, head on over to Dottie’s in Pittsfield for the Domingo Brunch featuring Robin O’Herin. On the Sunday afternoon “winery and brewery circuit,” you can see Gina and Ben (Gina Coleman and Ben Kohn) at Balderdash Cellars in Richmond or Jack Waldheim at Antimony Brewing in Lenox. Meanwhile, local favorite Melissa Brinton performs at portaVia in Dalton.
Something Else
In our Something Else category is the Kids Concerts with Terry A La Berry and Friends at the Colonial Theatre in Pittsfield.
You can read about all of these performances and more in our day-by-day show rundown below or jump right to our music calendar. Please note that our deadline for inclusion in the weekly narrative above and the day-by-day listing below is Wednesday at noon. Check our music calendar for shows we’ve added after our weekly publication deadline. Use the subscribe button below to receive this free weekly rundown of upcoming performances in your inbox each Monday. And if I missed a performance, please contact me, and I’ll add it to the calendar.
Monday
8:00 pm – 10:00 pm James Hatem and Miwi La Lupa @ Methuselah Bar & Lounge, Pittsfield.
Tuesday
No Performances.
Wednesday
6:30 pm – 9:30 pm Kris Allen Trio @ The Lion's Den, Stockbridge.
6:30 pm – 8:30 pm Rees Shad Trio @ Ostrich Room at Apple Tree Inn, Lenox.
Thursday
6:30 pm – 8:30 pm The Lucky Three Gypsy Jazz @ Ostrich Room at Apple Tree Inn, Lenox.
7:00 pm – 9:00 pm Calliope Cafe @ The Stationery Factory, Dalton.
7:00 pm – 8:30 pm Tipsy Carol McBoozle’s Holiday Sing-Along @ The Foundry, West Stockbridge.
7:00 pm – 8:30 pm Winter Concert @ Bard College at Simon's Rock, Great Barrington.
7:30 pm – 10:30 pm Clare Maloney and The Great Adventure @ Egremont Barn, South Egremont.
Friday
6:30 pm – 9:30 pm Luke Franco Trio @ Ostrich Room at Apple Tree Inn, Lenox.
7:00 pm – 10:00 pm Jon Berman @ Antimony Brewing, Lenox.
7:00 pm HOT PLATE HOLIDAY PARTY + ALESTER @ Hot Plate Brewing Co, Pittsfield.
7:00 pm Sounds of the Season @ First Congregational Church of Lee, Lee.
7:00 pm – 10:00 pm Diva & The Dirty Boys @ The Lion's Den, Stockbridge.
7:00 pm – 10:00 pm Mr. Doubtfire @ Firefly Gastropub, Lenox.
7:30 pm An Evening of Holiday Jazz with Tim Jones @ Colonial Theatre, Pittsfield.
7:30 pm Railway Concerts Presents: Vance Gilbert @ Studio 9, North Adams.
7:30 pm – 9:00 pm Love’s Pure Light @ St. Mark's Church, Pittsfield.
7:30 pm – 10:30 pm Dead man’s Waltz plays Jerry Garcia Band @ Egremont Barn, South Egremont.
8:00 pm – 9:30 pm Fall 2024 Jazz Concert @ Bard College at Simon's Rock, Great Barrington.
8:00 pm – 10:00 pm DCSC: Shinbone Alley with Bonnie Milner & Deirdre Murtha @ Race Brook Lodge, Sheffield.
Saturday
12:00 pm Kids Concerts with Terry A La Berry and Friends @ Colonial Theatre, Pittsfield.
2:00 pm – 5:00 pm Mike Duffy @ Balderdash Cellars, Richmond.
3:00 pm – 4:00 pm Aston Magna Family Day and Concert @ St. James Place, Great Barrington.
3:00 pm – 5:00 pm Stockbridge Festival Chorus in Concert @ First Congregational Church of Stockbridge, Stockbridge.
4:30 pm – 5:45 pm Williams College Chamber Music Gala @ The Clark Art Institute, Williamstown.
7:00 pm – 10:00 pm Johnny Irion @ The Lion's Den, Stockbridge.
7:00 pm All Of Us @ Methuselah Bar & Lounge, Pittsfield.
7:00 pm – 10:00 pm Tom Savoy @ Antimony Brewing, Lenox.
7:00 pm GREG HALL @ Hot Plate Brewing Co, Pittsfield.
7:00 pm Brett & Steve’s 2-Man Acoustic Jam @ Knox Trail Inn, East Otis.
7:00 pm Jason & Trev @ Route 8 Pub, Becket.
7:00 pm TLI Presents: BSO Holiday Brass @ Tanglewood, Lenox.
7:00 pm Sounds of the Season @ First Congregational Church of Lee, Lee.
7:30 pm – 10:00 pm The Priest – A Judas Priest Tribute @ The Stationery Factory, Dalton.
7:30 pm – 10:30 pm Holiday Spectravaganza! (And Jenny’s Birthday) @ Egremont Barn, South Egremont.
7:30 pm – 8:30 pm Vocalis Youth Choir: Songs of the Season @ St. James Place, Great Barrington.
7:30 pm – 8:45 pm Northern Berkshire Chorale @ Williams College, Williamstown.
8:00 pm – 11:00 pm Skeeter Creek @ Proprietor's Lodge, Pittsfield.
8:30 pm – 10:30 pm Tim Regusis Trio @ Ostrich Room at Apple Tree Inn, Lenox.
Sunday
10:00 am – 12:00 pm Domingo Brunch featuring Robin O’Herin @ Dottie's and Dorothy's, Pittsfield.
12:00 pm – 3:00 pm Jazz Brunch with Limited Release Trio @ Race Brook Lodge, Sheffield.
1:00 pm – 4:00 pm Melissa Brinton @ portaVia, Dalton.
2:00 pm – 4:00 pm Performing Artists in Residence Concert @ The Clark Art Institute, Williamstown.
2:00 pm – 5:00 pm Gina & Ben @ Balderdash Cellars, Richmond.
3:00 pm – 4:15 pm Yule for Fuel 2024 @ Zion Lutheran Church, Pittsfield.
3:00 pm TLI Presents: BSO Holiday Brass @ Tanglewood, Lenox.
3:00 pm – 4:30 pm Love’s Pure Light @ St. James Place, Great Barrington.
3:30 pm Naughty or Nice: Songs of the Season Holiday Cabaret @ Ventfort Hall, Lenox.
4:00 pm Close Encounters With Music: Vivace Chamber Orchestra – Tchaikovsky, Grieg, Britten, Boccherini, Barber @ Mahaiwe, Great Barrington.
4:00 pm Songs of the Season: Vocalis Youth Choir @ The Southfield Church, Southfield.
5:00 pm BERKSHIRE CONCERT CHOIR COMMUNITY SING @ Hot Plate Brewing Co, Pittsfield.
6:00 pm – 9:00 pm Jack Waldheim @ Antimony Brewing, Lenox.
6:30 pm – 9:30 pm Michael Junkins and Friends @ The Lion's Den, Stockbridge.
Please get out and support your local musicians and venues!
— Mark @ Music in the Berkshires