Music in the Berkshires: Week of May 29

Coming off the Memorial Day weekend and entering the first days of June, our calendar contains 34 live music shows across Berkshire County. This week, we’ve decided to switch things up a bit and organize our rundown by day rather than 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.

Wednesday

You can start your week off with some jazz by seeing the Don Mikkelson Trio at The Lion’s Den in Stockbridge. The trio will be playing from  5:30 pm – 8:30 pm. Or, you can catch Katherine Winston at the Ostrich Room at the Apple Tree Inn in Lenox from 7:00 pm – 9:00 pm. Katherine is a Massachusetts-based singer/songwriter and American Idol alum who blends country and pop influences.

Thursday

Over the past two weeks, 9 Great Berkshire Outdoor Concert Series were announced, including Berkshire Busk, Berkshire Botanical Gardens, and 7 other outdoor summer concert series, including Naumkeag. Their Naumkeag at Night series kicks off with their first show on Thursday with Trio Candela, who will be playing from 5:00 pm – 8:00 pm. Naumkeag is a Trustees of the Reservation property based in Stockbridge and has incredible views. In addition to listening to the great music, you can walk the beautiful grounds. 

Another option on Thursday is Latin Nights feat. Natalia Bernal and Jason Ennis at the Ostrich Room at the Apple Tree Inn in Lenox, playing from 7:00 pm – 9:00 pm. Just down the road at The Lion’s Den in Stockbridge, you can catch Pittsfield folk artist Melissa Brinton who is playing from 7:00 pm – 10:00 pm. You can learn more about Melissa here.

Over at Egremont Barn, Lexi Weege & JJ Slater are playing from 7:30 pm – 10:30 pm. Lexi Weege is a Western Mass-based singer/songwriter combining the best of classic country, Motown, and soul. She’ll be joined by guitarist JJ Slater, known for his UMASS Amherst band Humble Digs. You can learn more about Lexi and listen to her and JJ here.

Dream Away Lodge in Becket is featuring two performers on Thursday night. From 8:00 pm – 9:00 pm you can catch Brooklyn-based musician, singer, and composer David Nagler. And then from  9:30 pm – 11:30 pm stay on to see English singer-songwriter and guitarist Bridget St. John

Friday

On Friday, we find nine different performances on our calendar. 

Colby Lewis will play guitar and sing at the Lift Bistropub at Bousquet in Pittsfield from 6:00 pm – 9:00 pm. I had the opportunity to see Colby perform recently at a friend’s party and thoroughly enjoyed his covers of classic rock and pop songs.

Over in Lenox, Wanda Houston will be performing from 6:00 pm – 9:00 pm at Gateways Inn, while Laura Tupper & Bobby Sweet will be playing from 7:00 pm – 10:00 pm at the Ostrich Room at Apple Tree Inn.

Just down the road in Stockbridge at The Lion’s Den, you can Great Barrington-based Americana singer-songwriter Lisa Michelle Anderson playing from 7:00 pm – 10:00 pm. Lisa was voted best Singer-Songwriter by the Minnesota Music Academy and has opened for Warren Zevon, The Jayhawks, Marianne Faithfull, Lowen & Navarro, and others. You can learn more about Lisa and listen to her music here.

Further south in Sheffield, you’ll find the Apollo Suns Live performing at Race Brook Lodge. They are a 9-piece instrumental collective from Winnipeg, Manitoba, fusing the influence of jazz, rock, and psychedelic music. You can learn more about and listen to them here.

Playing up in Dalton at the Stationery Factory is the Atlanta Rhythm Section, pictured above, who have been part of the Southern Rock scene for over 50 years. They will likely be playing many of their hits, including So Into You and Imaginary Lover.

Down at Egrmont Barn, Elizabeth & The Catapult and Jenna Nicholls will be playing from 7:30 pm – 10:30 pm. Elizabeth & The Catapult just released their fifth album, sincerely, e. Elizabeth recently collaborated with Sara Bareilles on Apple TV’s “Little Voice,” and you can listen to her here. Also hailing from NYC, Jenna Nichols will bring her ukulele to the stage, playing music ranging from New Orleans-style dirges to 1920’s style original ballads. Recently, Jenna has toured with Ingrid Michaelson. You can learn about her and listen to her music here.

Also on Friday, The Liquid Courage, who plays classic rock, will be performing at 8:00 pm at the Great Barrington VFW, while Misty Blues will be at Dream Away Lodge in Becket, also at 8:00 pm.

Saturday

On Saturday night, you’ll find 8 performances within the county. If you want to listen to some up-and-coming talent, consider heading to Williams College at 11:00 am to hear the Class Day Recital, featuring graduating seniors from the Williams music school.

If jazz is your thing, then you may want to listen to Suzi Stern Trio from 6:00 pm – 9:00 pm at Gateways Inn in Lenox. Perhaps a Celtic Choir is more to your taste? If so, then see the Vocalis Youth Choir at The Southfield Church in Southfield at 7:00 pm. The Vocalis Youth Choir is a vocal ensemble based in Great Barrington for young people who are passionate about singing.

Wanda Houston is playing from 7:00 pm – 10:00 pm at The Lion’s Den in Stockbridge, while Jeffrey Foucault will be performing at Egremont Barn at 7:30 pm. He’ll be bringing a mix of blues, country, rock’n’roll, and folk to the Barn’s stage. You can learn more about him and listen to him here.

Just up the road at the Guthrie Center, Matt Nakoa will be performing at 8:00 pm as part of their Troubadour series, and another troubadour-rocker, Johnny Irion & Friends, will be playing from 8:00 pm – 10:00 pm at the Ostrich Room at the Apple Tree Inn in Lenox. Johnny recently released his album Working My Way Down, collaborating with Mike Stinson. You can learn more about Johnny and listen to his music here.

Dream Away Lodge in Becket will be featuring Home Body, playing from 8:00 pm – 11:30 pm. They will be bringing their blend of electronic, new wave, and experimental pop music to the lodge. You can read about them and listen to their music here.

Sunday

Sunday offers classical music lovers three great opportunities to find music joy. At 3:00 pm, Berkshire Lyric: Brahms German Requiem is performing at Seiji Ozawa Hall at Tanglewood. At 4:00 pm, Baroque lovers will want to see The Organ Masters II: Baroque Organ and Brass at the First Congregational Church of Great Barrington. The performance features Peter Sykes playing the historic Roosevelt Organ, joined by John Thiessen, Baroque and Modern Trumpet, and Adam Gautille, Modern Trumpet. At 6:00 pm, you can listen to Aston Magna: The Devil’s in the Tales at St. James Place in Great Barrington. Their program includes a revival of the partnering of two morality tales: Alessandro Scarlatti’s “Humanitá e Lucifero” and Igor Stravinsky’s “L’Histoire du Soldat.”

There are two great outdoor concert series options for Sunday afternoon. First, at 3:30 pm, you can see En Diablada: Jason Ennis & Natalia Bernal in Lilac Park on Main Street in Lenox as part of the Lenox Loves Music free concert series. Later, also outdoors in Lenox, you can catch the Pride Concert with Pamela Means Jazz Project. The performance is at The Mount in Lenox from 5:30 pm – 7:30 pm. Pamela Means Jazz Project performs originals, jazzed-up classic covers, and great American songbook jazz standards from the 1930s-1950s.

Sunday night features four great shows. Namoli Brennet will be performing at 7:00 pm at The Foundry in West Stockbridge. Namoli is a folk-rock singer/songwriter who has self-released 13 albums since her debut in 2002. She is a 4-time Outmusic award nominee who was featured in the inaugural Trans 100 list. You can learn more about Namoli and listen to her music here.

At Egremont Barn, the trifecta of Joy Askew/Lauren Balthrop/Oropendola will perform from 7:00 pm – 10:00 pm. Joy Askew has played alongside artists such as Peter Gabriel, Laurie Anderson, Joe Jackson, and opened for David Bowie and David Byrne (two of my heroes), among others. You can learn about and listen to Joy here. Folk-pop singer/songwriter Lauren Balthrop plays music in the lineage of Carly Simon, Joni Mitchell, and Carole King – you can learn more about her here. Joanna Schubert is the Brooklyn-based singer/keyboardist behind Oropendola – you can learn more about her here.

Down in Sheffield at Race Brook Lodge, you can hear a synthesis of Moroccan traditional music and electronic, dubbed-out funk at Barnspace Concert: Club D’Elf at 7:00 pm. You can learn more and listen to the band here.

And finally, Massachusetts-based Stella Kola plays at Dream Away Lodge in Becket 8:00 pm – 11:30 pm. You can listen to her here.


With the onset of this glorious summer weather, we hope you’ll get out this week and enjoy live music in The Berkshires!

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