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Today

Jazz Night with Paul Ostermayer and Friends

Tito's Mexican Bar and Grill 34 Depot St, Pittsfield, MA

Liven up your Tuesday evenings with Paul Ostermayer and Friends at Tito's Mexican Bar & Grill!

Free

Nate Martel

Methuselah Bar & Lounge 391 North Street, Pittsfield, MA

Will you welcome this incredibly and fabulously talented musician with an infectious smile? Nate will be the one artist you will be glad you’ve witnessed. This man has greatness in him and it is entwined in his beautiful and stunning music and remarkable voice and he plays his heart out! Nate is from Pioneer Valley, […]

Free

Colby Lewis & Steve Ide

Ostrich Room at Apple Tree Inn 10 Richmond Mountain Road, Lenox, MA

No further information available.

Free

The JoAnne Redding Trifecta

The Lion's Den 30 Main Street, Stockbridge, MA

October Jazz Series, Spirits & Live Music for All, 6:30 - 9:30 PM. With Benny "Fingers" Kohn and Dan Broad on keys and upright bass respectively, supporting the vocal artistry of Ms. Redding, this jazz night is a sure bet for a great time.

$10

Witchy Wednesday

Hot Plate Brewing Co 1 School St, Pittsfield, MA

Join us for our second-annual Witchy Wednesday celebration. We’ll be teaming up with some of our favorite vendors, offering Zodiac-inspired flights, and we’ll have performances from Luna Faun and Greg Hall!

Free

The Lucky 3

Ostrich Room at Apple Tree Inn 10 Richmond Mountain Road, Lenox, MA

No further information available.

Free

Colby Lewis & Steve Ide

The Lion's Den 30 Main Street, Stockbridge, MA

October Den Sessions, Spirits & Live Music for All, 7 - 10 PM

$10

Halloween Party w/Misty Blues

Dream Away Lodge 1342 County Rd, Becket, MA

Annual Halloween party with Misty Blues

$25 – $30

Tipsy MacBoozle’s “Hallowscream-Along”

The Foundry 2 Harris St, West Stockbridge, MA

Come join Tom Truss as Tipsy MacBoozle in the “Hallowscream-Along.” Straight back from her world tour with Donna Summers, Sting and JD Vance, Tipsy will lead everyone through a horror show of songs like GhostBusters, The Monster Mash, Black Magic Woman, The Candy Man, Somebody’s Watching Me and Witchy Woman. Your heart will open, your […]

$20

Halloweeed! Halloween Party with The Weeeds

Egremont Barn 17 Main Street, South Egremont, MA

Its our annual Halloween party! Come in costume!! And enjoy The Wild Weeeds and special guests!

$15

Fall Music Series – Jack Waldheim

Jiminy Peak Mountain Resort 37 Corey Rd, Hancock, MA

Join us on Halloween for the finale of our 13 Nights haunt followed by music in the Tavern with Jack Waldheim. He will perform his One Man Band show and fill the joint with a unique blend of rock, blues and original tunes. You’ll be sayin’, “Really!? There’s only one dude on stage!” Stop in […]

Free

Halloween Dance Party with Sinkane & The Pass

Race Brook Lodge 864 S Undermountain Rd, Sheffield, MA

We are beyond thrilled to be teaming up with  THE PASS BERKSHIRES the first time to host an Electro-Funk Halloween Getdown! Join us on Thursday Oct 31 for a two part adventure! Part one starts at 6pm on the porch where your ticket provides access to a pre-concert lounge and mini-expo on the porch hosted by […]

$20 – $30
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