This week we have 45 live music shows in Berkshire County. We start the week with the Juneteenth Holiday and have two performances on Monday to help you celebrate. Throughout the week, we run the whole gamut of shows, from rock, pop, and blues to jazz and opera. The Tanglewood popular music season kicks off Friday with The Steve Miller Band.
If you prefer, you can jump right to our Calendar to see all events rather than read our performance rundown. For those new to our website, note that you can search for a specific artist, filter the performances based on genre, venue, or location, and view events in both a calendar and map view in addition to the default list view. Use the subscribe button below to receive this weekly rundown of upcoming performances in your inbox.
Monday
To celebrate the Juneteenth holiday, you can choose between one of two shows on Monday evening. At 5:00 pm at The Mount in Lenox, you can see the Concert with John Hughes, an innovative kora (West African harp) player, percussionist, and vocalist. At the same time, Misty Blues performs at The Barn Kitchen & Bar in Williamstown. Misty Blues is a Berkshire County regular – you can read more about Gina Coleman and the band and listen to their latest music here.
Tuesday
Tuesday evening also brings two shows, both in north county. At 7:00 pm, you can catch the Lincoln, Nebraska-based Folk/Americana band The Wildwoods at Studio 9 in North Adams. The band is in the midst of a blistering 40+ show nationwide tour after launching their latest album, Foxfield Saint John. You can learn more about and listen to the band here.
Just down the road at Firehouse Cafe & Bistro in Adams, Chantell & Friends perform at 7:00 pm. Chantell brings the soulful sounds of Chicago to Berkshire County.
Wednesday
The Town of Great Barrington Concert Series hosts Berkshire Sings from 5:30 – 7:15 pm at the “Grover’s Corner Gazebo” behind the Great Barrington Town Hall.
Jazz lovers will find two great performances to choose from. The multi-talented Berkshire favorite Andy Wrba and Friends play from 5:30 – 8:30 pm at The Lion’s Den in Stockbridge as part of the Den’s June Jazz Series. Up the road a bit in Dalton at portaVia, Mary Ann Palermo continues her June residency, performing at 6:00 pm.
In Lenox at the Ostrich Room at Appletree Inn, Katherine Winston performs from 7:00 – 9:00 pm. Katherine is a Massachusetts-based singer/songwriter and American Idol alum who blends country and pop influences. You can learn more about and listen to her music here.
After performing Tuesday at Studio 9, The Wildwoods travel a bit south and go on at 8:00 pm at Dream Away Lodge in Becket.
Thursday
Thursday night offers nine shows to choose from. You can get your evening moving at Gateways Inn in Lenox with Jason Fenton/Swing Dance from 6:00 – 9:00 pm.
At 7:00 pm at Berkshire Palate in Pittsfield, you can listen to Buffalo-based Maria Sebastian. She plays folk, rock (’90s alternative and classic), classic country, Americana, American songbook pop, and jazz, as well as her own original music, a blend of these. You can learn more about and listen to Maria here.
In Stockbridge at The Lion’s Den, you can groove to the Western MA-based Stombox Trio, made up of Evelyn Harris, John Cabán, and Paul Kochanski. They will play from 7:00 – 10:00 pm; you can learn more about them here.
Down in Sheffield, Race Brook Lodge is hosting a concert in their Barnspace with Sarah Lee Guthrie from 7:00 – 11:00 pm. The member of the legendary Guthrie family has traveled up from Austin for this stop on her tour.
Up in Dalton, two other Guthrie family members take the stage at The Stationery Factory. Serena & Krishna Guthrie perform at 7:30 pm.
Cantrip performs at the Egremont Barn at 7:30. We had the chance to see this band at The Foundry earlier this year and thoroughly enjoyed them. With their Edinburgh, Scotland roots, they play border pipes, fiddle, and guitar. Being of Scottish heritage, I am particularly mesmerized by border and bagpipes. You can learn more about and listen to them here.
Up at Dream Away Lodge in Becket, The Riverboat Gamblers perform from 7:30 pm – 10:30 pm, while down in Lenox at the Ostrich Room at Apple Tree Inn, LA-based Chris Murphy will be making his first of three Berkshire appearances on his packed world tour. Chris’ performances feature a variety of music that may include blues, bluegrass, folk, country rock, gypsy, Celtic, ambient post-rock, indie rock, Americana, and other world music influences. Learn more about and listen to him here.
Friday
We hit our peak live music day of this week, with 11 performances to choose from on Friday, starting with Lady Di & the Dukes playing from 5:30 – 7:15 pm as part of the Town of Great Barrington Concert Series. You’ll find the performance at the gazebo behind the Town Hall.
Teri Roiger performs jazz from 6:00 – 9:00 at Gateways Inn in Lenox.
Also in Lenox, Tanglewood kicks off their popular music season series with the Steve Miller Band with Very Special Guest Bruce Hornsby & The Noisemakers at 7:00 pm. These two bands need no further description.
Just down the road from Tanglewood at the Lion’s Den in Stockbridge, Zan & The Winter Folk perform from 7:00 – 10:00 pm as part of the June Den Sessions. The band was named “2018’s Best Folk Band” by The Alt and nominated for “Folk Artist of the Year” at the 2019 Capital Region Eddies Awards. You can learn more about and listen to them here.
Further south in Sheffield at Race Brook Lodge, you can catch Canada-based Mamas Broke as part of their Down County Social Club series. The duo, who will perform from 7:00 – 10:00 pm, play fiddle, banjo, guitar, and mandolin. You can learn more about and listen to them here.
Up in Pittsfield at the Rusty Anchor Pub, Brian Benlien will perform from 7:00 – 10:00 pm.
NY City-based Milton, pictured above, takes the stage at 7:30 pm at the Egremont Barn. Milton is a Berkshire favorite – we’ve seen him many times and will be at this performance, too. I connected with Milton this last week over Zoom, and he is our Featured Musician this week. Many New Yorkers will know his song “In the City,” but I’m also a fan of many other songs from his five albums.
Opera fans have a treat this week when the Mahaiwe in Great Barrington hosts Boston Early Music Festival: Francesca Caccini’s Alcina for two performances of this comic opera, the first of which is Friday night at 8:00 pm.
Newly opened Antimony Brewing in Lenox hosts local performer Adelaide Punkin from 8:00 – 11:00 PM. We just started tracking Antimony’s shows in our calendar this week.
At Dewey Hall in Sheffield, you will find another performance by Chris Murphy, who we described above. TapRoot Sessions: Chris Murphy Concert goes from 8:00 to 9:15 pm.
To cap off Friday night, you can see the Hudson Valley-based performer Noah Harley at 8:00 pm at Dream Away Lodge in Becket. Noah writes and plays traditional music on guitar, banjo, and piano, and you can learn more about him and listen to him here.
Saturday
Saturday offers nine shows during the day and evening. Opera lovers have a second chance on Saturday at 3:00 pm to see Boston Early Music Festival: Francesca Caccini’s Alcina at the Mahaiwe in Great Barrington.
At 5:00 pm, you can listen to Nashville-based folk singer-songwriter Louise Mosrie as part of the Becket Arts Center’s Music Brings Communities Together program. Loiuse’s songs won top awards at Kerrville Folk Festival, Wildflower! Festival, Telluride Bluegrass Festival, and Falcon Ridge Folk Festival. Her song “Home” debuted at #1 on the Folk DJ charts in January 2010 and went on to be one of the most-played albums that year on that chart. You can learn more about and listen to her here.
Jazz lovers will find the George Oldziey Duo playing from 6:00 – 9:00 pm at Gateways Inn in Lenox, while Chris Murphy performs his third show in The Berkshires at The Lion’s Den in Stockbridge from 7:00 – 10:00 pm.
At The Southfield Church at 7:00 pm, you can listen to an evening with the American Songbook with Wanda Houston & Robert Kelly.
In Pittsfield at the Rusty Anchor Pub, The Hot Shot Hillbillies Duo, who promise to get you up dancing, will jam from 7:00 – 10:00 pm.
Just down the road in Lenox, Pug & John perform from 8:00 – 11:00 pm at Antimony Brewing in Lenox.
To wrap up your Saturday night, the Dream Away Lodge in Becket is hosting two performers: Big Trash will play from 8:00 – 9:30 pm, while Boston-based Rick Maguire (of Pile) will perform from 9:30 – 11:00. You can learn more about Pile and Rick and listen to their music here.
Sunday
After being closed for a week to install a new HVAC system, Dottie’s Coffee Lounge in Pittsfield should be back open by Sunday morning, just in time for Domingo Brunch w/ Fannie Pack from 10:00 am to noon – but you might want to call to make sure the construction project is finished, and Dottie’s has re-opened.
From 11:00 am – 2:00 pm at Starving Artist Cafe & Creperie in Lee, StringSmith will perform some “GypZbilly” music, which he describes as a mix of “Gypsy, Jump Blues, Rockabilly, a smattering of Country blues, with a dash of the Carib.”
Race Brook Lodge in Sheffield hosts Jazz Brunch with Bobby MacVeety from noon to 3:00 pm in their Stagecoach Tavern.
From 2:00 – 5:00 pm at Antimony Brewing in Lenox, you can see Steve Adams & Tangled Party, while just down the road in Stockbridge at The Lion’s Den, Michael Junkins & Friends will play from 5:30 – 8:30 pm as part of the June Jazz Series.
Sunday evening, at 7:30, you can listen to Dayna Kurtz at The Foundry in West Stockbridge. Dayna crosses many genres in her music, including American jazz, pop, blues, folk, and country. She has received accolades from a number of great artists and was named Female Songwriter of the Year in 1997 by the National Academy of Songwriters. You can learn more about and listen to her music here.
Rounding out Sunday, Dream Away Lodge in Becket has two shows. First, at 7:30 pm, Paulette Humanbeing will take the stage in the music room. Then at 8:30, Cape Cod-based Chandler Travis Three-O will go on. They are a hard band to describe – you can learn more about them and listen to them here.
That’s our rundown for the week of June 19th. Make a plan to get off the couch and out of the house and support the amazing live music scene we have in The Berkshires.
— Mark @ Music in the Berkshires