Best Entertainment events in Great Barrington This Weekend | February 21 - 22

Q: What are the upcoming Entertainment events in Great Barrington?

Here are the upcoming events in Great Barrington: "Howl's Moving Castle" (2004), Indigo Room: Chrissi Poland, Piano Lover's Dream (6th Edition), Gutterly Ridiculous Bowling Night

Entertainment events in Great Barrington this Weekend

Fri, 20 Feb, 2026 - 07:00 PM

"Howl's Moving Castle" (2004)

14 Castle St, Great Barrington, MA, United States, Massachusetts 01230

14+ Interested
Sat, 21 Feb, 2026 - 08:00 PM

Indigo Room: Chrissi Poland

20 Castle St, Great Barrington, MA 01230-1513, United States

5+ Interested
Sat, 21 Feb, 2026 - 06:30 PM

Piano Lover's Dream (6th Edition)

Flynn Pianos Workshop & Gallery

USD 34
Sat, 21 Feb, 2026 - 05:00 PM

Gutterly Ridiculous Bowling Night

67 State Rd, Great Barrington, MA, United States, Massachusetts 01230

5+ Interested

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Fri, 29 May • 07:00 PM

Prom for Mom! - 80's 90's 00's

Aqua Turf Club

21+ Interested

|

USD 69
Featured

Sat, 25 Apr • 06:00 PM

Freedom Riders Dinner & Comedy Concert Fundraiser with Mike Bova

American Legion Post 14, West Street, Vernon, CT, USA

9+ Interested

|

USD 35
Fri, 27 Feb • 06:00 PM

Galentine's Yap & Berries Party | Women's Emotional Healing Galentine’s Party

Capital District Regional Market - Farmers Market

Newly Added

|

USD 65
Sat, 21 Feb Onwards

DANCE PRACTICE PARTY

Fred Astaire Dance Studios - Suffield

Newly Added

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USD 20
Thu, 19 Feb Onwards

LATIN MIX GROUP CLASS

Fred Astaire Dance Studios - Suffield

Newly Added

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USD 35
Thu, 19 Feb Onwards

Albany Scavenger Hunt For Couples - SHOW LOVE (Date Night!!)

Recommended scavenger starting point or other city spot of your choice! (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED)

Newly Added

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USD 10
Thu, 19 Feb Onwards

Kingston Scavenger Hunt For Couples - SHOW LOVE (Date Night!!)

Recommended scavenger starting point or other city spot of your choice! (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED)

Newly Added

|

USD 10
Thu, 19 Feb Onwards

Hudson Scavenger Hunt For Couples - SHOW LOVE (Date Night!!)

Recommended scavenger starting point or other city spot of your choice! (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED)

Newly Added

|

USD 10
Sun, 15 Feb Onwards

Philmont Scavenger Hunt For Couples - SHOW LOVE (Date Night!!)

Recommended scavenger starting point or other city spot of your choice! (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED)

Newly Added

|

USD 10

Frequently Asked Questions

What are the upcoming Entertainment events in Great Barrington?

Here are the upcoming Entertainment events in Great Barrington:

"Howl's Moving Castle" (2004) is happening on Fri 20 Feb 2026 from 7:00 PM onwards at 14 Castle St, Great Barrington, MA, United States, Massachusetts 01230
Indigo Room: Chrissi Poland is happening on Sat 21 Feb 2026 from 8:00 PM onwards at 20 Castle St, Great Barrington, MA 01230-1513, United States
Piano Lover's Dream (6th Edition) is happening on Sat 21 Feb 2026 from 6:30 PM onwards at Flynn Pianos Workshop & Gallery, Great Barrington
Gutterly Ridiculous Bowling Night is happening on Sat 21 Feb 2026 from 5:00 PM onwards at 67 State Rd, Great Barrington, MA, United States, Massachusetts 01230