Join us for live music & entertainment upstairs in the bar all summer long...

MONDAYS

It's Karaoke Night.
What more do we have to say?

Come in, sign up and be a star!

10pm
THURSDAYS

More fun than you remember the 80’s really being -
our 80’s NIGHT is serious fun.

Expect big hair, leggings and lots of dancing...

The last call sing along to “Don’t Stop Believin’ is mandatory!
80s night
FRIDAYS

Winslow’s and The Berkshire Brewing Co. present the acclaimed
Benny Sharoni Quartet from Boston.

Enjoy BBC tastings and fabulous hard bop jazz -
8:30pm - 11pm.

Playing June 25th until Sept. 3rd.
SATURDAYS

The sounds of summer...classic rock 'n' roll with The Origin.

From the Beatles, Tom Petty, Elvis Costello, to Steely Dan.

You name it, they can play it.
SUNDAYS

We're shaking things up every Sunday night by featuring an eclectic cast of local legends as well as national acts who play everything from "can't sit down" polka fusion, to blues, folk, rock and uncharted territories beyond. Sundays at Winslow's are not to be missed!

Chandler Travis Trio Randy and the Oak Trees Will Evans Polka Dan's Beetbox Band!
Our Current Sunday Lineup:

July 3rd
Chandler Travis Three-O

July 10th
Randy and the Oak Trees

July 17th
Jose Ayerve is A Severe Joy

July 24th
Will Evans

July 31st
Polka Dan's Beetbox Band!

August 7th
Soul Night with Chris Kelly (just like 80's night, but funkier)

August 14th
Will Evans

August 21st
Chandler Travis Three-O

August 28th
Polka Dan's Beetbox Band!

September 4th
Randy and the Oak Trees


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