As October wraps up and we gear up for Halloween, the end of daylight saving time, and a busy November filled with the World Series, Election Day, and Thanksgiving, one thing remains constant: the vibrant Berkshire live music scene. This week, we have 40 fantastic shows lined up, offering something for every taste—from classical, jazz, and rock to pop, electronic, dance, folk, blues, and Celtic tunes. No matter what the season brings, these performances will surely add a joyful soundtrack to your week. Below are some highlights for the week ahead, followed by our comprehensive show rundown.
Classical and Opera
We have three classical performances in the county this week. On Friday night, enjoy the Berkshire Symphony at Williams College, which is performing works by Cristóbal MarYán, Eduard Lalo, and Jean Sibelius. Saturday night, you have a special opportunity to enjoy Classical Concert: Sō Percussion at The Clark Art Institute in Williamstown. The internationally renowned genre-defying percussion chamber group is teaming up with the Williams College Department of Music for this performance. The Clark has labeled it a classical concert, so we’ve categorized it here. Sunday afternoon, you can participate in the Fauré Requiem Community Sing at Trinity Episcopal Church in Lenox. This All Souls Day Requiem service is conducted by Noah Palmer and includes special guests Ryan José LaBoy and the Berkshire Children’s Choir.
Jazz
We have six jazz performances this week. On Tuesday night, you’ll find Jazz Night with Paul Ostermayer and Friends at Tito’s Mexican Bar and Grill in Pittsfield. Wednesday night, The JoAnne Redding Trifecta performs at The Lion’s Den in Stockbridge. Joining vocalist Redding are Benny “Fingers” Kohn on keys and Dan Broad on upright bass. Thursday night, The Lucky 3 perform at the Ostrich Room at Apple Tree Inn in Lenox, and Friday night, enjoy Piano with Harris MacDonald at the Ostrich Room.
Sunday morning, chill out at the Domingo Brunch featuring duo David Bartley and Pete Toigo at Dottie’s in Pittsfield. On Sunday night, you’ll find Michael Junkins and Friends at The Lion’s Den. This week, Michael features Aaron Dean on saxophone.
Popular (Rock, Pop, Folk, Blues, etc.)
The popular music category dominates our calendar this week, with over 25 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 Tuesday afternoon, with the Housie Shakers performing on the Dunham Mall in downtown Pittsfield. Immediately after this performance, head down North Street to catch Nate Martel at Methuselah Bar & Lounge. On Wednesday, Witchy Wednesday takes place at Hot Plate Brewing in Pittsfield and features music by Greg Hall. Local favorites Colby Lewis & Steve Ide are at the Ostrich Room at Apple Tree Inn – they will perform again Thursday night at The Lion’s Den.
Halloween night (Thursday) offers three special celebrations. The Dream Away Lodge in Becket is hosting a Halloween Party w/Misty Blues, while The Egremont Barn is hosting Halloweeed! Halloween Party with The Weeeds. Race Brook Lodge in Sheffield is hosting a Halloween Dance Party with Sinkane & The Pass. Sinkane fuses elements of krautrock, electronica, reggae, free jazz, and funk rock with Sudanese pop. He’s collaborated with many music greats, including David Byrne (of Talking Heads and one of my heroes), Money Mark (of Beastie Boys), Damon Albarn (of Blur), and others.
Friday night, music returns to the Firefly Gastropub in Lenox after a summer break with The BTU’s performing. Clara Guatta performs at the Dia De Los Muertos Celebration at Hot Plate Brewing. Up in North Adams, you’ll find Studio 9 Presents: Krishna Guthrie, while Melissa Brinton performs at The Lion’s Den. Johnny Irion & Friends with special guest Lisa Michelle Anderson perform at Egremont Barn. Irion will play music from his critically acclaimed new album, Sleeping Soldiers of Love, and songs from his next album coming in 2025. Local psych-rock band Vaguely Pagan is at Dream Away Lodge, or you can catch A Celtic Music Harvest: Hildaland with David Patton and Claudine Langille at Dewey Hall in Sheffield.
Saturday night’s choices are fewer than usual, but the quality of music is incredibly high. ANOHNI (pictured above) is back at MASS MoCA in North Adams for a solo performance. She is the lead singer of the band Anohni and the Johnsons, formerly known as Antony and the Johnsons. She performs a mix of electronic, pop, dance, and experimental music. King Kyote is back at The Egremont Barn, bringing his unique blend of blues and Americana music. We saw him perform at The Barn earlier this year and thoroughly enjoyed his show – watch a video from that show on our Instagram page. Folk-rocker Jefferson Hamer is at The Lion’s Den, bluegrass singer-songwriter Kate Prascher is at Dream Away Lodge, and Mike Duffy is at Antimony Brewing.
Sunday afternoon, you can catch the Riverside Brothers at portaVia in Dalton. Sunday evening offers three performances. The Boston-based genre-bending band Alester comes to Hot Plate Brewing Co. Mike Cobb & The Crevulators perform in the music room at Dream Away Lodge, and Number One Babe performs a solo show at Tourists in North Adams.
Something Else
In our Something Else category, you’ll find Thursday and Friday night performances of Tipsy MacBoozle’s “Hallowscream-Along” at The Foundry in West Stockbridge. Tipsy will lead the audience through Halloween-inspired songs like “Ghostbusters,” “The Monster Mash,” “Black Magic Woman,” “Witchy Woman,” and more. Or, head down to Race Brook Lodge Friday night for Fandango de Los Muertos with Pulso de Barro, which explores Son Jarocho (“Veracruz Sound”) Mexican folk music. Lovers of music in our Something Else category may also enjoy Saturday night’s Classical Concert: Sō Percussion at the Clark Art Institute in Williamstown, which we mentioned in our Classical music category. After listening to the ensemble’s rich range of genre-defying music all afternoon, I think the audience will experience something unique.
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
No Performances.
Tuesday
4:00 pm – 7:00 pm Housie Shakers @ Dunham Mall, Pittsfield.
5:30 pm – 8:30 pm Jazz Night with Paul Ostermayer and Friends @ Tito’s Mexican Bar and Grill, Pittsfield.
7:00 pm Nate Martel @ Methuselah Bar & Lounge, Pittsfield.
Wednesday
6:30 pm – 9:30 pm The JoAnne Redding Trifecta @ The Lion’s Den, Stockbridge.
6:30 pm – 8:30 pm Colby Lewis & Steve Ide @ Ostrich Room at Apple Tree Inn, Lenox.
7:00 pm Witchy Wednesday @ Hot Plate Brewing Co, Pittsfield.
Thursday
6:30 pm – 8:30 pm The Lucky 3 @ Ostrich Room at Apple Tree Inn, Lenox.
7:00 pm – 11:55 pm Halloween Party w/Misty Blues @ Dream Away Lodge, Becket.
7:00 pm – 10:00 pm Colby Lewis & Steve Ide @ The Lion’s Den, Stockbridge.
7:30 pm – 10:00 pm Tipsy MacBoozle’s “Hallowscream-Along” @ The Foundry, West Stockbridge.
7:30 pm – 10:30 pm Halloweeed! Halloween Party with The Weeeds @ Egremont Barn, South Egremont.
8:00 pm – 11:00 pm Halloween Dance Party with Sinkane & The Pass @ Race Brook Lodge, Sheffield.
8:00 pm – 10:00 pm Fall Music Series – Jack Waldheim @ Jiminy Peak Mountain Resort, Hancock.
Friday
4:00 pm – 7:00 pm Piano with Harris MacDonald @ Ostrich Room at Apple Tree Inn, Lenox.
7:00 pm – 10:00 pm Benny Fingers & Friends featuring Susan Davis & Tom Parker Supper Club @ Dottie’s and Dorothy’s, Pittsfield.
7:00 pm – 10:00 pm The BTU’s @ Firefly Gastropub, Lenox.
7:00 pm – 10:00 pm Dia De Los Muertos Celebration @ Hot Plate Brewing Co, Pittsfield.
7:00 pm – 10:00 pm Livio Gravini @ Antimony Brewing, Lenox.
7:00 pm Studio 9 Presents: Krishna Guthrie @ Studio 9, North Adams.
7:00 pm – 10:00 pm Melissa Brinton @ The Lion’s Den, Stockbridge.
7:30 pm – 10:00 pm Tipsy MacBoozle’s “Hallowscream-Along” @ The Foundry, West Stockbridge.
7:30 pm Berkshire Symphony @ Williams College, Williamstown.
7:30 pm – 10:30 pm Johnny Irion & Friends with special guest Lisa Michelle Anderson @ Egremont Barn, South Egremont.
8:00 pm – 11:00 pm Fandango de Los Muertos with Pulso de Barro @ Race Brook Lodge, Sheffield.
8:00 pm – 10:00 pm Vaguely Pagan @ Dream Away Lodge, Becket.
8:00 pm – 11:00 pm Halloween Party @ Zinky’s Pub, Dalton.
8:00 pm – 9:30 pm A Celtic Music Harvest: Hildaland with David Patton and Claudine Langille @ Dewey Hall, Sheffield.
Saturday
7:00 pm – 10:00 pm Mike Duffy @ Antimony Brewing, Lenox.
7:00 pm – 8:30 pm Classical Concert: Sō Percussion @ The Clark Art Institute, Williamstown.
7:00 pm – 10:00 pm Jefferson Hamer @ The Lion’s Den, Stockbridge.
7:30 pm – 10:30 pm King Kyote @ Egremont Barn, South Egremont.
8:00 pm – 10:00 pm Kate Prascher @ Dream Away Lodge, Becket.
8:30 pm ANOHNI @ MASS MoCA, North Adams.
Sunday
10:00 am – 12:00 pm Domingo Brunch featuring duo David Bartley and Pete Toigo @ Dottie’s and Dorothy’s, Pittsfield.
1:00 pm – 4:00 pm Riverside Brothers @ portaVia, Dalton.
3:00 pm – 5:00 pm Fauré Requiem Community Sing @ Trinity Episcopal Church, Lenox.
5:00 pm Alester @ Hot Plate Brewing Co, Pittsfield.
6:30 pm Michael Junkins and Friends @ The Lion’s Den, Stockbridge.
6:30 pm – 9:00 pm Mike Cobb & The Crevulators @ Dream Away Lodge, Becket.
8:00 pm – 9:30 pm Number One Babe (Solo) @ Tourists, North Adams.
Please get out and support your local musicians and venues!
— Mark @ Music in the Berkshires