Makaya McCraven
HOPE Center for the Arts, Springfield
Thursday, Oct. 9 at 7 p.m.
HOPE Center for the Arts is an amazing and relatively new organization that partners with public schools, counselors, and regional arts organizations to provide youth with free access to real training, state-of-the-art equipment and teaching artists, happening in the former CityStage theater. Now, they’re rolling out a concert series featuring big names like Judy Collins, Take 6, Arturo Sandoval, the Blind Boys of Alabama, and Makaya McCraven. Raised just outside Amherst, Massachusetts, Makaya McCraven cut his musical teeth in western Mass and is now an internationally celebrated visionary in the world of modern jazz.
Hedwig and the Angry Inch
Shea Theater, Turners Falls
Thursday, Oct. 9 – Friday, Oct. 17
Greenfield’s Arena Civic Theatre is proud to present a raw, rebellious new production of the cult-classic rock musical Hedwig and the Angry Inch. Fueled by a blistering rock score and razor-sharp wit, Hedwig and the Angry Inch is the story of a genderqueer East German rocker navigating heartbreak, identity, and radical self-invention. This production honors the show’s gritty roots while pushing it into bold new territory.
Sunday in the Park with George
Northampton Center for the Arts at 33 Hawley Street
Friday, Oct. 10 – Saturday, Oct. 18
Step into a world of art, imagination, and creation with Stephen Sondheim and James Lapine’s Pulitzer Prize–winning musical. Inspired by Georges Seurat’s well-known pointillist painting, the musical follows the passionate but misunderstood painter, as he grapples with love, legacy, and the challenge of balancing life and art. This production is presented by The K and E Theater Group who, under the leadership of Ken Comia and Eddie Zitka, have been presenting thought-provoking theater since 2017.
Mahaiwe Theater: Indigo Room Grand Opening
Mahaiwe Theater, Great Barrington
Friday, Oct. 10 – Sunday, Oct. 12
We’re always happy to welcome a new performance venue to our region! The Indigo Room is a new flexible performance space in the former Great Barrington firehouse building at 20 Castle Street, next door to the historic Mahaiwe theater. Grand Opening events happening throughout the weekend include performances by jazz vocalist Ann Hampton Callaway, blues guitarist Guy Davis, family-friendly musician Terry A La Berry, a comedy night, and more. The ribbon cutting ceremony is Sunday at 1 p.m.
Berkshire Pride: Prideoween
The Stationary Factory, Dalton
Friday, Oct. 10 from 8 p.m. – 11 p.m.
This annual celebration brings together the queer and trans community and allies for a night of fun, costumes, music, and connection, complete with a high-energy drag show with Bella Santarella, Poppy DaBubbly, Vuronika Baked and Jackie Leggs, dancing with DJ BFG, and more. The theme for this year’s Prideoween is Music Icons. Dress the part!
The Paradise City Arts Fall Festival
Three County Fairgrounds, Northampton
Saturday, Oct. 11 – Monday, Oct. 13
This is more than an art fair. It’s a full-on experience with live music, delicious local food, and a vibe that’s equal parts gallery, street fair, and creative playground. Discover creations from 200 curated artists and makers from across the country. Two dining tents, flanking a new performance stage, will create a courtyard/ beer garden environment. On Saturday, artists will show their creations until 7 p.m. Then, Whiskey Treaty Roadshow will hit the stage for a “Paradise Presents” show sponsored by The Parlor Room Collective and Signature Sounds.
Berkshire Botanical Garden's Annual Harvest Festival
Berkshire Botanical Garden, Stockbridge
Saturday, Oct. 11 and Sunday, Oct. 12 from 10 a.m. – 5 p.m.
This weekend, Berkshire Botanical Garden will host a celebration of community, culture, and the region’s agricultural heritage. The festival features lots of activities for kids, live music, 50 artisan craft vendors, food trucks, a plant sale, and the popular “Accessorize” pop-up shop with gently used clothing, jewelry, hats, and scarves. New this year — a scarecrow walk.
The Ashfield Fall Festival
Saturday, Oct. 11 and Sunday, Oct. 12 from 10 a.m. – 5 p.m.
This is one of my favorite town festivals. I love the low-tech vibe of the lawn games, the local music, and I spend lots of time (and pick up holiday gifts) in the arts and craft fair tents. But what propels me to the festival every year? The sweets — home-made fresh pumpkin donuts, blueberry cobbler and apple pie.
New England Noir
Glendale Ridge Vineyard, Southampton
Saturday, Oct. 11 from 12 p.m. – 6 p.m.
New England Noir is New England's first Black and Multicultural wine experience. This year features music curated by Bryan-Michael Cox, and DJ Mars. Bring a blanket, lawn chairs, and picnic basket, and enjoy gorgeous afternoon. Plus! There’s also a business brunch happening on Sunday at 11 a.m. with speakers, networking and mimosas!
Norma Dream Album Release Party
Bombyx, Florence
Saturday, Oct. 11 at 7 p.m.
Fronted by Florence native Norma Jean Haynes, Norma Dream is coming to the Bombyx stage to celebrate their debut studio release Mercy Drops. In addition to a full-band rendition of the record, this night features a screening of a new music video, "Strawberry Wine," shot on 16mm film and directed by award-winning filmmaker Lilit Danielyan, and a performance by the Mia Friedman Band. Come early and order a pie from Augustine's Pizza. Plus! Norma Dream will be on The Fabulous 413 this week for “Live Music Friday.”
Springfield Symphony Orchestra Season Opener
A Night in Italy: Verdi, Respighi, & Rota
Springfield Symphony Hall
Saturday, Oct. 11 at 7:30 p.m.
From Verdi’s La Forza Del Destino to the old sounds of Ancient Airs and Dances by Respighi to the monumental orchestral colors in Respighi’s Pines of Rome, to the contemporary orchestral suites by Menotti and from the popular film, Godfather, the SSO celebrates Italian composers and culture through iconic works throughout the centuries. The audience will witness a meaningful collaboration with members from the Springfield Symphony Youth Orchestras and a unique surround sound experience at the climax of Pines of Rome.
Art Naturally: Leaf Prints for Leaf Peepers
Great Falls Discovery Center, Turners Falls
Sunday, Oct. 12 from 10:30 a.m. – 12 p.m.
Discover nature through story, poetry and art! Create an art piece inspired by autumn using paint, paper, gel and even leaves, with instruction and techniques. For adults, teens, and children ages 6 and up (accompanied by an adult). All materials are provided for this free event. Meet in the Great Hall at 10:30 a.m. for complete instructions.
Valley Classical: The Harlem Quartet
Sweeney Concert Hall, Smith College
Sunday, Oct. 12 at 3 p.m.
The GRAMMY award-winning Harlem Quartet kicks off Valley Classical’s 2025–2026 season with “Echoes of Inspiration,” an eclectic program that weaves together works by Beethoven, Benjamin Britten, Caroline Shaw, and Guido López Gavilán. The Harlem quartet love to thoughtfully present traditional masterpieces alongside complementary contemporary works. Their ability to seamlessly traverse various musical styles while maintaining a signature sound is a testament to their exceptional musicianship and artistic vision.
An Evening with Jeff Daniels
Iron Horse, Northampton
Monday, Oct. 13 at 7 p.m.
He’s the actor, right? Yes, but in 1976, Jeff Daniels bought a Guild D-40 from Herb David’s Guitar Studio in Ann Arbor, Michigan, threw it in the back of his old Buick, and moved to New York City. That guitar led to a creative outlet, became a solace, a road into the artist that he didn’t know existed. Now, over 40 years later, he’s still writing songs, singing them, and playing.
Paul Beaubrun
The Drake, Amherst
Tuesday, Oct. 14 at 8 p.m.
Port-au-Prince native Paul Beaubrun is very much of Haiti. Beaubrun is the son of Theodore “Lolo” and Mimerose “Manze” Beaubrun, both founding members of the internationally celebrated band Boukman Eksperyans. He draws musical influence from across the Caribbean, the United States, and throughout the African diaspora. And his virtuosic guitar playing recalls both Ali Farka Touré and Jimi Hendrix.
COMING SOON
The Vagabond Ball featuring Bella’s Bartok, The Slambovian Circus of Dreams, and The Picky Bastards
Colonial Theater, Pittsfield
Friday, 10/17 at 7:30 p.m.
Tuesday Morning Music Club: Mary Brown Bonacci, mezzo-soprano and Ed Orgill, saxophone, with Scott Bailey, piano
Trinity United Methodist Church, Springfield
Tuesday, Oct. 21 at 10:30 a.m.
Wicked: Immersive sing-along film screening and cOZplay event hosted by Monte Belmonte
Tillis Performance Hall, UMass
Friday, Oct. 24 at 6:30 p.m.
Caleb Teicher & Nic Gareiss in the Doris Duke Theatre
Jacob’s Pillow, Beckett
Friday, Oct. 24 – Sunday, Oct. 26
Winterpills Album Release Party
Iron Horse, Northampton
Saturday, Nov. 8 at 7 p.m.