This week, our calendar contains 37 live music shows across Berkshire County. That’s a lot – but slightly down from the staggering 50(!) shows last week. This 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.
Rock, Pop, Folk, and Blues
Wednesday
Your week starts off Wednesday with Massachusetts-based singer/songwriter and American Idol alum Katherine Winston playing at the Ostrich Room at Apple Tree Inn in Lenox from 7:00 – 9:00 pm. Katherine has three more shows in her May residency at the Ostrich Room. You can learn more about her and listen to her here.
Thursday
Thursday night presents three great opportunities for live shows: Sample the Cat will be performing at the Egremont Barn at 7:30 pm. They are from Berkshire County and play a fusion of rock, blues, funk, and soul. You can learn more about them and listen to their music here.
Bobby Sweet & Lara Tupper are up the road at The Lion’s Den in Stockbridge, playing at 7:00 pm. And Jake Klar, Party of The Sun go on at 8:00 pm up at Dream Away Lodge in Becket.
Friday
Friday night, you can catch Jack Waldheim at the LIFT Bistropub at Bousquet in Pittsfield. Jack just opened for the Jon Pousette-Dart Trio this past weekend at The Stationery Factory. He’ll be playing starting at 6:00 pm.
Misty Blues will be playing at Firefly Gastropub in Lenox at 7:00 pm Friday, and also in Lenox at the same time, Melissa Brinton will be at the Ostrich Room at Apple Tree Inn. Melissa is a singer/songwriter from Berkshire County who plays a blend of folk, rock, jazz, and pop. You can learn more about this Pittsfield resident and listen to her here.
David Wilson of Chatham County Line will be playing at 7:00 pm Friday at The Lion’s Den in Stockbridge. David is making a tour through the Berkshires and playing at three venues this week. You can learn about his band Chatham County Line and listen to their music here. Up at Dream Away Lodge, you can see Lexi Weege & JJ Slater Band at 8:00 pm.
Also, on Friday, upstate New York singer-songwriter Al Olender continues her east coast tour with a stop at the Egremont Barn at 7:30 pm. You can learn more about her and listen to her music, including her newest album, Easy Crier, here.
Saturday
Saturday offers a dizzying ten shows in this category. We won’t list them all – you can peruse them on our Events Calendar, but here are a few highlights:
The Refrigerators with Hotshot Hillbillies will be performing a benefit concert at The Stationery Factory in Dalton at 7:30 pm. The Refrigerators are a 10-piece, horn-fueled party band from the Capital Region of NY. Proceeds to support Dalton Lions Club and 12th Man Go Blue.
Beatles cover band The Eggmen will be at Egremont Barn at 7:30. The band features Berkshire-based musicians Tom and Gigi Teeley, Steve and Carol Ide, Rob Putnam, and Tom Major. We recently interviewed Steve Ide – you can read about him here.
Amy Ryan Band will be at Firefly Gastropub in Lenox, and Greg Humphreys will be at the Lion’s Den in Stockbridge. Dave Wilson of Chatham County Line will be at the Ostrich Room at Apple Tree Inn. Winterpills will be up at Dream Away Lodge in Becket at 8:00 pm.
Sunday
Sunday afternoon offers an opportunity to see American folk and blues songwriter Tom Rush at the Colonial Theatre in Pittsfield (pictured above). He’ll perform at 2:00 pm.
Also, on Sunday afternoon, you can join in The Hilltown Blues Jam at Knox Trail Inn in East Otis from 2:00 – 5:00 pm.
Sunday evening, you can wrap up your weekend with Dave Wilson of Chatham County Line, playing at Dream Away Lodge in Becket at 8:00 pm.
Jazz
Jazz lovers will find great opportunities for live performances nearly all week long, starting off with Monday Jazz Night at 7:00 pm at Hot Plate Brewing in Pittsfield. This week Hot Plate will be featuring Andy Wrba, Ben Kohn, Conor Meehan, and special guest Chantell McFarland.
Wednesday night offers two great Jazz shows. The Kris Allen Trio will play at The Lion’s Den in Stockbridge from 5:30 to 8:30 pm, while Sweet Tooth and Fingers (Ed Moran & Benny Kohn Duo) will play further north at portaVia restaurant in Dalton.
Michael Junkins will be performing at Gateways Inn in Lenox on Friday night from 6:00 to 9:00 pm. Saturday night at the same time and place, you can catch Bobby MacVeety.
Moving to Sunday morning, Dottie’s Coffee Lounge in Pittsfield is offering Domingo Brunch with vocalist Susan Dillard with David Bartley, Piano. They will play improvisational Jazz, Blues, Soul, Musical Theater, and a touch of pop, from 10:00 am to noon.
You can put the finishing touch on your weekend with Michael Junkins & Friends, playing from 5:30 to 8:30 pm at the Lion’s Den in Stockbridge.
Classical
Classical lovers have a dilemma this week. There are three great classical music performances – but all on Sunday afternoon!
The Cantilena Chamber Choir performs Bach’s Magnificat in D at Trinity Episcopal Church in Lenox from 3:00 to 5:00 pm.
At the same time, Aston Magna Chamber Players: The Music of Franz Schubert will perform at St. James Place in Great Barrington.
And at 4:00 pm, Mahaiwe in Great Barrington is offering Close Encounters With Music: The Escher String Quartet—Tchaikovsky, Ravel, Ruth Crawford Seeger.
Something Different
Live music in The Berkshires does not always fit into neat and tidy genre classifications like Rock, Jazz, or Classical. Here are a few performances that feature something different.
On Tuesday from 6:30 – 7:30 pm, support the musicians of the future by seeing Pittsfield High School String Orchestra Concert at the Berkshire Athenaeum in Pittsfield, MA
On Thursday, you have another wonderful opportunity to listen to new talent by attending Calliope Cafe at The Stationery Factory in Dalton. High school students from around Berkshire County perform music, dance, and poetry on a stage for friends, family, and the community.
Also, on Thursday, you can take in Latin Nights feat. Natalia Bernal and Jason Ennis at the Ostrich Room at Apple Tree Inn in Lenox. They will play from 7:00 to 9:00 pm.
On Friday, Race Brook Lodge in Sheffield is offering Barnspace Concert: The ReMemberers featuring John de Kadt from 7:00 to 10:00 pm. The show is billed as “an evening of mesmerizing song, music, and story.”
We hope you’ll get out this week and enjoy live music in The Berkshires!