Leading into Memorial Day weekend, our calendar contains 31 live music shows across Berkshire County. Similar to last week, we’ve chosen to organize our run-down by music genre.
If you prefer, you can jump right to our Calendar to see all events rather than read our performance run-down. 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.
Classical
This week, we have just two classical performances on our music calendar, both on Sunday. The timing is right so that you can catch them both!
Tanglewood is hosting an early season show at the Seiji Ozawa Hall this Sunday at 2:00 pm with Berkshire Choral International in Concert, Anthony Trecek-King, conductor.
Later on Sunday at 6:00 pm, the West Stockbridge Chamber Players Spring Concert is taking place a the West Stockbridge Historical Society. This is a benefit concert for the restoration of the Old Town Hall in West Stockbridge. The performance features world-class musicians.
Jazz
This is a strong jazz week in The Berkshires, with eight performances between Wednesday and Sunday.
Jeff Stevens Trio is playing as part of the Lion’s Den May Jazz series on Wednesday evening, starting at 5:30 pm. Also on Wednesday, Sweet Tooth and Fingers (Ed Moran & Benny Kohn Duo) will perform from 6:00 – 9:00 pm at portaVia in Dalton.
On Friday, you can catch the Michael Junkins Duo, playing from 6:00 – 9:00 pm at Gateways Inn in Lenox. Also on Friday, the hard-swinging jazz band, The Lucky 5, plays at Dream Away Lodge in Becket from 8:00 to 11:00 pm. The band blends 30’s and 40’s style swing with gypsy and Parisian flavors to create a unique blend of music. Read more about them and listen to their music here.
On Saturday, you can catch Karen Tchougourian at the Gateways Inn in Lenox at 6:00 pm.
Sunday presents three opportunities to listen to Jazz. The Race Brook Lodge in Sheffield is hosting Jazz Brunch with Charlie Tokarz from 12:00 to 3:00 pm.
Just a bit later in the afternoon, at 3:30, you can see Susan Dillard, Dave Bartley & Dan Broad outdoors at Lilac Park in downtown Lenox. This is the first show in the 2023 LenoxLovesMusic! series at Lilac Park.
And to cap off the day and get you ready for Memorial Day, you can see Michael Junkins & Friends from 5:30 – 8:30 pm over at The Lion’s Den in Stockbridge.
Hip-hop and Rap
We have two great hip-hop and rap shows this week.
On Friday at 7:30 pm, Jackson Whalan will be at the Egremont Barn. Jackson is a lyricist and producer from Berkshire County who raps and makes beats to uplift and inspire listeners around the world. You can read more about him and listen to his music here.
On Saturday at 8:00 pm, Brooklyn-based Phony Ppl perform at MASS MoCA. They bring a unique genre-bending mix of hip hop, R&B, neo-soul, and art rock to the stage. You can learn more about them and listen to their music here.
Rock, Pop, Folk, Americana, and Blues
There are 19 shows in this category this week. We won’t cover all the shows, but here are some highlights:
Wednesday
Your week starts off Wednesday with Massachusetts-based singer/songwriter and American Idol alum Katherine Winston continues her May residency at the Ostrich Room at Apple Tree Inn in Lenox from 7:00 – 9:00 pm. She is a Massachusetts-based singer/songwriter and American Idol alum. You can learn more about her and listen to her here.
Thursday
The Lion’s Den in Stockbridge is hosting Diva & The Dirty Boys. They are described as “Soulful and powerful vocalist meets Dirty Boy Rock- gritty and talented instrumentals 60s & 70s.” Their show starts at 7:00 pm.
Also on Thursday, Corner House plays at Egremont Bard at 7:30 pm. They are a Boston-based band that incorporates old-time Scottish, progressive bluegrass, and folk. You can read more about them and listen to their music here.
Up in Dalton at The Stationery Factory, the Legendary Shack Shakers w/ Dex Romweber & Viva Le Vox take the stage at 7:30. Led by their frontman Col. JD Wilkes, the band plays a mix of swamp blues, rock n’ roll, and hillbilly music. You can learn more and listen to them here.
Friday
Solo singer Scott Silvia puts his spin on old and new songs from 6:00 – 10:00 pm over at Knox Trail Inn in East Otis.
The next two shows present some personal agita since two of my favorites play simultaneously on the same night. Milton performs at the Ostrich Room at the Apple Tree Inn at 7:00 pm. I first saw Milton at the Ostrich Room and enjoyed him so much that I saw him again at Dream Away Lodge last Saturday.
Clare Maloney & The Great Adventure plays at the same time at The Lion’s Den in Stockbridge. I wrote about Clare’s performance at the Ostrich Room two weeks ago, having seen her for a second time. I’ve been listening to her songs Dream Within a Dream and Dorado incessantly on Spotify. Both songs put me in an incredibly buoyant mood.
Fortunately, Clare is also playing Saturday night at the Ostrich Room, so if you can’t see her Friday, you have another chance – and a new show has been posted in June for Clare down at Egremont Barn.
Saturday
Saturday also has many great options to choose from. Chris Merenda & The Wheel is opening the season at The Guthrie Center in Great Barrington at 8:00 pm Saturday. Chris, pictured above, is “a songwriter, multi-instrumentalist, and lead singer who has been performing and re-inventing his sound for the past two and a half decades.” He is also well-known as a member of the Whiskey Treaty Road Show. You can learn more about him here.
Clare Maloney & The Great Adventure will return to the Ostrich Room on Saturday at 7:00 pm, while Vaguely Pagan will play at the Lion’s Den in Stockbridge at 7:00 pm.
Johnny Irion & Ian O’Neil (of Deertick) will be performing at Dream Away Lodge in Becket at 8:00 pm, while further up the road in East Otis, Horns B Funk will be playing at Knox Trail Inn. They’ll entertain you with great tunes by Chicago, Bonnie Raitt, Bruce Springsteen, Steve Winwood, Steely Dan, and more.
Hot Sauce, featuring local musicians Steve Ide, Tom Major, Benny Kohn, and Miles Lally, will be at Egremont Barn at 7:30 pm, and down the road at Fiddleheads in Great Barrington, the dance/party band Lucky Bucket will be playing at 7:00 pm.
In North County, the Adams Theater presents Misty Blues Celebrates Queens of the Blues. This new production by Misty Blues pays homage to the matriarchs of the blues: Bessie Smith, Big Mama Thornton, Ruth Brown & Koko Taylor.
Sunday
Sunday morning from 10:00 am to noon, you can catch Domingo Brunch with the StringSmith, Kevin Smith at Dottie’s Coffee Lounge in Pittsfield. StringSmith musician and guitar builder Kevin Smith brings his “GypZbilly” music, which is a variety of genres from Blues to Rockabilly, Reggae, Folk, and beyond.
On Sunday evening, you can see the Queler & Farber Family Band at Dream Away Lodge in Becket at 8:00 pm.
Something Different
As we did last week, here is a run-down of a few shows that fall outside the tidy boundaries of the genres listed above.
On Thursday at 7:00 pm, you can listen to Latin Nights feat. Natalia Bernal and Jason Ennis at the Ostrich Room at the Apple Tree Inn in Lenox.
Also on Thursday, you can hone your dance moves when Dewey Hall in Sheffield offers Taproot Cajun Dance w/ The Empty Bottle Ramblers. The Empty Bottle Ramblers play traditional Cajun music from southwest Louisiana, featuring driving accordion two-steps, aching fiddle waltzes, and sassy blues, all sung in Cajun French.
And on Friday night, don’t miss The Berkshires’ Academy for Advanced Musical Studies (BAAMS) 3rd Anniversary Concert at 7:30 at the Adams Theatre in Adams. This is the BAAMS Third Anniversary Benefit Concert, featuring an exciting night of live musical performances from the BAAMS’ world-class music Faculty, Students, and Special Guests.
We hope you’ll get out this week and enjoy live music in The Berkshires!