Name: Katherine Winston
Start: 2025-10-31T19:00:00-04:00
End: 2025-10-31T22:00:00-04:00
Location: Ostrich Room at Apple Tree Inn

October 2025
October 27, 2025 @ 8:00 pm

TROY MILLETTE & SURPRISE GUESTS

Tourists 915 State Rd, North Adams, MA

Vermont’s TROY MILLETTE is equal parts thoughtful and lively– a cocktail of rock, pop, folk, and americana music that grapples with love, loss, and the human experience. Millette’s emotive and […]

Free
October 29, 2025 @ 6:00 pm - 8:00 pm

Whistle and The Stack

portaVia 645 Main St, Dalton, MA

Hey Folks…Music WEDs, 6-8pm! Wednesday Residence…Who’s in the Window?! WED OCT 1, 6-8pm…Whistle and The Stack (Jordan Weller)

Free
October 29, 2025 @ 6:00 pm - 9:00 pm

Colby Lewis & Steve Ide

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

A beloved Berkshire duo, Colby Lewis and Steve Ide bring timeless songs from the ’60s, ’70s, and beyond to life with rich harmonies, soulful guitar, and easy charm. Their performances […]

Free
October 29, 2025 @ 6:30 pm - 9:30 pm

Fumi Tomita Quartet

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

October Jazz Sessions.

$10
October 29, 2025 @ 7:30 pm

Skye Consort & Emma Björling

The Foundry 2 Harris St, West Stockbridge, MA

Skye Consort & Emma Björling perform trans-Atlantic arrangements of songs and tunes from Sweden, Norway, Ireland, Scotland, England, Québec, Acadia, the USA, as well as original compositions. Each musician brings […]

$25 – $30
October 29, 2025 @ 8:00 pm

ANDREW YEE

Tourists 915 State Rd, North Adams, MA

GRAMMY Award-winning cellist Andrew Yee will be in residence at TOURISTS creating a new album of solo cello works by Bach and American cellist and composer Arthur Russell. Yee has […]

Free
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 2025