October has arrived in the Berkshires, ushering in another exciting week of live music. This week’s lineup features singer-songwriter Suzanne Vega and a special benefit concert honoring the life and legacy of Air Force Staff Sergeant Jacob “Jake” Galliher, showcasing four fantastic bands. With 42 performances across the county—ranging from classical and jazz to rock, blues, and folk—there’s something for everyone. Below are some highlights for the week ahead, followed by our comprehensive show rundown.
Classical and Opera
We have four classical performances this week. Friday evening, enjoy the Williams Chamber Players at Williams College. They will perform works by Turina, Somei Satoh, and Dohnanyi. Sunday afternoon offers three performances. The fall series at the South Mountain Concert Hall in Pittsfield comes to a close with the Chamber Ensemble St. Martin in the Field, performing works by Shostakovich, Dvořák, and Mendelssohn. At St. James Place in Great Barrington, you’ll find Crescendo: Nature in Vivaldi’s Sounds, performing three works by the Italian composer. Or, you can visit the Sandisfield Arts Center to hear Bill Taylor and Friends performing several of Taylor’s pieces, which are classically inspired with hints of jazz and show tunes, along with pieces by Shostakovich and Camille Saint-Saens.
Jazz
We have eight jazz performances in the county this week. The music starts Tuesday with Jazz Night with Paul Ostermayer and Friends at Tito’s Mexican Bar and Grill in Pittsfield. Friday night, you can catch some New Orleans jazz when the Soggy Po Boys perform at The Egremont Barn. Saturday evening offers three jazz performances. You’ll find The Natalia Bernal “En Diablada” Quartet at the West Stockbridge Old Town Hall, The Lucky Five at The Lion’s Den in Stockbridge, and a Jazz In The Berkshires Concert—A Letter To Bill Evans, a tribute to the legendary jazz pianist and composer, at The Clark Art Institute in Williamstown.
Sunday morning, you’ll find the Domingo Brunch featuring duo David Bartley and Pete Toigo at Dottie’s and Dorothy’s in Pittsfield. At midday, you can catch the Jazz Brunch with Bobby MacVeety at Race Brook Lodge in Sheffield. Then, in the evening, you’ll find Michael Junkins and Friends at The Lion’s Den.
Popular (Rock, Pop, Folk, Blues, etc.)
The popular music category dominates our calendar this week, with nearly 30 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 Wednesday when The Cold Stares visit The Stationery Factory in Dalton. The band plays a mix of blues, southern, and hard rock – their song “Any Way the Wind Blows” has over 9 million streams on Spotify. Also on Wednesday, Steve Gunn makes a stop at Tourists in North Adams as part of their Sing for your Slumber program. Gunn’s music blends blues, folk, free jazz, and psych rock.
Thursday night offers three shows. Local favorites Colby Lewis & Steve Ide play at The Lion’s Den in Stockbridge, while the line-up of Glenn Jones, Thalia Zedek w/Karen Sarkisian Damon & Naomi visit Dream Away Lodge in Becket. Or, you can head up to Belltower Records in North Adams to see three performers in the shop: Minibeast, Ian St. George Band, KaneLoggiaHYPOTHESIS.
Friday night, you’ll find the Misty Blues Band at the October Supper Club at Dottie’s and Dorothy’s in Pittsfield, the first night in a month-long Friday residency. Pigpen Theatre Company comes to Tourists, with their unique brand of theatre, music, and film. Dan Blakeslee is back at Dream Away Lodge in Becket. We enjoyed seeing Dan there last August when he sang “Almost in Mexico” off his album Road Hymns, recorded in a cabin at Dream Away. You can watch a video of him performing the song on our Instagram Page here. Fun fact: Dan is the artist who developed the artwork for several of The Alchemist’s regionally famous beers, including Heady Topper and Focal Banger. Finally, music is back at Jiminy Peak Mountain Resort in Hancock. Mike McMann starts the fall season playing classic and southern rock, bluegrass, and roots music.
Saturday night is bursting with great performances. Suzanne Vega (pictured above) comes to the Mahaiwe in Great Barrington with her show “Old Songs, New Songs and Other Songs.” The artist famous for “Tom’s Diner” and “Luka” is featured in the current issue of Berkshire Magazine – learn about her musical journey and current tour in the interview.
An important event on Saturday night is the Jam for Jake: A Jake Galliher Foundation Fundraiser at the Colonial Theatre in Pittsfield. The evening celebrates the life and legacy of Air Force Staff Sergeant Jacob “Jake” Galliher, who tragically lost his life on November 29th, 2023, while serving our nation abroad. The event features several great bands, including Black Dog, The Rev Tor Band, The Whiskey Treaty Roadshow, and Misty Blues. All ticket proceeds will benefit The Jake Galliher Foundation, dedicated to honoring Jake’s memory and supporting individuals who exemplify his character and spirit.
I’m incredibly excited to have Sean Rowe with opener Jenna Nicholls perform at The Egremont Barn. I started listening to Rowe in advance of his show at The Guthrie Center this summer, but alas, the show sold out, so we did not attend. As a parent, his song “Follow Your Trail” brings me to tears. Other shows on Saturday night include the Celtic band Kilashandra at Route 8 Pub in Becket and Stella Kola performing right up the road at Dream Away Lodge. In North Adams, you’ll find Anywhere Presents: Katy Pinke at Studio 9.
Sunday afternoon, on the “winery and brewery circuit,” you’ll find Les Chrostowski at Antimony Brewing in Lenox and Paul Zarvis at Balderdash Cellars in Richmond. Up the road at portaVia in Dalton, the Misty Blues Trio will perform. In the evening, The Egremont Barn is hosting FODFest – the Friends of Danny Festival, which honors the life of Daniel Pearl, the Wall St. Journal reporter who was abducted and murdered by extremists in Pakistan shortly after 9-11. The evening is packed with talent, with performers such as Wanda Houston, Jackson Whalan, Bree Nicola, JoAnne Spies, Rees Shad, Katherine Winston, Christine Bilé, Soul Prophet, Todd Mack, EMCEE P.O.E.T.R.E.Y, and others. Up at Dream Away Lodge, catch Moon Hollow, which performs music inspired by folk, Americana, bluegrass, alt-country, and early jazz.
Something Else
In our Something Else category, we have Skye Consort & Emma Björling on Tuesday evening at The Foundry in West Stockbridge. They will present “an assortment of whirling polskas, groovy reels, passionate love songs, breathtaking hymns, and original compositions.”
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
5:30 pm – 8:30 pm Jazz Night with Paul Ostermayer and Friends @ Tito’s Mexican Bar and Grill, Pittsfield.
7:30 pm Skye Consort & Emma Björling @ The Foundry, West Stockbridge.
Wednesday
8:00 pm – 10:00 pm The Cold Stares @ The Stationery Factory, Dalton.
8:00 pm – 9:30 pm Steve Gunn @ Tourists, North Adams.
Thursday
7:00 pm – 8:00 pm Minibeast, Ian St. George Band, KaneLoggiaHYPOTHESIS show at the shop @ Belltower Records, North Adams.
7:00 pm – 10:00 pm Colby Lewis & Steve Ide @ The Lion’s Den, Stockbridge.
7:30 pm – 9:30 pm Glenn Jones, Thalia Zedek w/Karen Sarkisian Damon & Naomi @ Dream Away Lodge, Becket.
Friday
5:00 pm – 8:00 pm Zarvis & Pug @ Balderdash Cellars, Richmond.
6:00 pm – 10:00 pm Misty Blues Band October Supper Club @ Dottie’s and Dorothy’s, Pittsfield.
7:00 pm – 10:00 pm Taraka DJ @ The Lion’s Den, Stockbridge.
7:00 pm – 10:00 pm Kollin Kozlowski @ Antimony Brewing, Lenox.
7:30 pm Williams Chamber Players @ Williams College, Williamstown.
7:30 pm – 10:30 pm Soggy Po Boys @ Egremont Barn, South Egremont.
8:00 pm – 9:30 pm Pigpen Theatre Company @ Tourists, North Adams.
8:00 pm – 10:00 pm Fall Music Series: Mike McMann @ Jiminy Peak Mountain Resort, Hancock.
8:00 pm – 10:00 pm Dan Blakeslee @ Dream Away Lodge, Becket.
Saturday
12:00 pm – 3:00 pm Pete Boyd @ Balderdash Cellars, Richmond.
7:00 pm – 10:00 pm Mark Franklin @ Antimony Brewing, Lenox.
7:00 pm Kilashandra @ Route 8 Pub, Becket.
7:00 pm – 8:30 pm The Natalia Bernal “En Diablada” Quartet @ West Stockbridge Old Town Hall, West Stockbridge.
7:00 pm – 10:00 pm Lucky Five @ The Lion’s Den, Stockbridge.
7:00 pm – 9:00 pm Concert: Jazz In The Berkshires—A Letter To Bill Evans @ The Clark Art Institute, Williamstown.
7:30 pm – 10:30 pm Sean Rowe with opener Jenna Nicholls @ Egremont Barn, South Egremont.
7:30 pm – 9:30 pm Jam for Jake: A Jake Galliher Foundation Fundraiser @ Colonial Theatre, Pittsfield.
7:30 pm Whiskey City Band @ Adams Theatre, Adams.
8:00 pm – 10:00 pm Fall Music Series: Billy Gilbert @ Jiminy Peak Mountain Resort, Hancock.
8:00 pm Suzanne Vega – Old Songs, New Songs and Other Songs @ Mahaiwe, Great Barrington.
8:00 pm – 10:00 pm Stella Kola @ Dream Away Lodge, Becket.
8:00 pm Mr. Doubtfire @ Knox Trail Inn, East Otis.
8:00 pm – 11:00 pm Hotshot Hillbillies @ Locker Room Sports Pub, Lee.
8:00 pm Anywhere Presents: Katy Pinke @ Studio 9, North Adams.
Sunday
10:00 am – 12:00 pm Domingo Brunch featuring duo David Bartley and Pete Toigo @ Dottie’s and Dorothy’s, Pittsfield.
12:00 pm – 3:00 pm Les Chrostowski @ Antimony Brewing, Lenox.
12:00 pm – 3:00 pm Jazz Brunch with Bobby MacVeety @ Race Brook Lodge, Sheffield.
12:00 pm – 5:00 pm Paul Zarvis @ Balderdash Cellars, Richmond.
1:00 pm – 4:00 pm Misty Blues Trio @ portaVia, Dalton.
3:00 pm – 5:00 pm Chamber Ensemble St. Martin in the Field @ South Mountain Concert Hall, Pittsfield.
4:00 pm – 6:00 pm Crescendo: Nature in Vivaldi’s Sounds @ St. James Place, Great Barrington.
4:00 pm – 5:30 pm Bill Taylor and Friends @ Sandisfield Arts Center, Sandisfield.
5:00 pm – 9:00 pm FOD Fest @ Egremont Barn, South Egremont.
6:30 pm – 9:30 pm Michael Junkins and Friends @ The Lion’s Den, Stockbridge.
7:30 pm – 9:30 pm Moon Hollow @ Dream Away Lodge, Becket.
Please get out and support your local musicians and venues!
— Mark @ Music in the Berkshires