Name: John Nalepa Duo
Start: 2025-10-31T20:00:00-04:00
End: 2025-10-31T22:00:00-04:00
Location: Jiminy Peak Mountain Resort

October 2025
October 30, 2025 @ 6:00 pm - 9:00 pm

Barbara Stein & Weird Birds

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

Barbara Stein is a Berkshires-based singer-songwriter and fingerstyle guitarist whose sound fuses alt-rock energy with Americana blues roots. Her performances are intimate yet powerful, weaving soulful lyrics and deft guitar […]

Free
October 30, 2025 @ 7:30 pm - 10:00 pm

CANCELED: The Nth Power with special opening set by Jackson Whalan

Buttonball Barn 17 Main Street, South Egremont, MA

The Nth Power has to cancel its New England shows. Proving that soul music can be exponentially greater than the sum of its parts, The Nth Power is on a […]

$25 – $30
October 30, 2025 @ 8:00 pm - 10:00 pm

Rounders Revival

Dream Away Lodge 1342 County Rd, Becket, MA

Rounders Revival invites you to share in an evening of light-hearted and uplifting acoustic music steeped deeply in the folk-americana traditions of universal story telling and soulful harmonies. Join in […]

Free
October 30, 2025 @ 8:00 pm - 10:00 pm

Jason & Trev

Jiminy Peak Mountain Resort 37 Corey Rd, Hancock, MA

Jason & Trev Acoustic are musical experience that specialize in a wide array of popular songs from the 1950’s to today. Whether it’s rhythm and blues, classic rock, folk, love […]

Free
October 31, 2025 @ 7:00 pm - 10:00 pm

Halloween II w/ Sean Connors and Fiendish

Route 8 Pub 3235 Main St, Becket, MA

Great Food Great Music Great People

Free
October 31, 2025 @ 7:00 pm - 10:00 pm

Katherine Winston

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

From the rolling hills of New England, Katherine Winston is a Singer/Songwriter whose music is a blend of country, folk/rock, and pop. Inspired by musical icons like Stevie Nicks, Brandi […]

Free
October 31, 2025 @ 7:00 pm - 10:00 pm

Wanda Houston

Firefly Gastropub 71 Church Street, Lenox, MA

A Dynamic Quartet Featuring Rhythm, Blues, Jazz & Soul from the 30s through the 70s. Wanda Houston is a professional singer, actress, and song stylist who has traveled the stages […]

Free
October 31, 2025 @ 7:30 pm

Tom Truss as Tipsy McBoozle in “Hallow-Scream-Along” Sing-Along

The Foundry 2 Harris St, West Stockbridge, MA

Tom Truss’s beloved character, Tipsy McBoozle hosts a harrowing sing-along with prizes, surprises, and an honorary multi-media scream contest with our very own birthday & B-Movie Scream Queen, Amy Brentano. […]

$20 – $25
October 31, 2025 @ 7:30 pm - 10:00 pm

Halloween Bash with the Wild Weeeds

Buttonball Barn 17 Main Street, South Egremont, MA

Get readuy for a night to remember on Hallowwen night! With The Weeeds! and more! Wear your best costumne!

$15 – $20
October 31, 2025 @ 8:00 pm

Natalie Merchant with Erik Della Penna: Autumn Acoustic Tour

Mahaiwe 14 Castle St, Great Barrington, MA, United States

Over her 40-year career Natalie Merchant has earned a reputation for being a songwriter and recording artist of rare quality, a captivating stage performer, and a skilled producer. She has […]

$71 – $81
October 31, 2025 @ 8:00 pm

Midnight 30 Halloween Party

Knox Trail Inn 1898 E Otis Rd, East Otis, MA

BOO! Our Halloween Parties are a scary great time! Wicked creative costumes, chilling Knoxtails, and best of all live music from Midnight 30! As always, no cover!

Free
October 31, 2025 @ 8:00 pm - 10:00 pm

John Nalepa Duo

Jiminy Peak Mountain Resort 37 Corey Rd, Hancock, MA

Enjoy a variety of sounds from this high energy duo, playing in the Tavern tonight to cap off our 13 Nights festivities!

Free

October 2025