Events and Things to Do in Gloucester, MA

Friday, September 11

Featured

A Band of Brothers - Not Just an Allman Brothers Tribute

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8:00 PM

The Cut - Stage • Studio • Restaurant • Bar, 177 Main St, Gloucester, MA

18+, Positive I.D. Required "A Band Of Brothers" isn't just an Allman Brothers tribute band; they're a powerhouse, uniting the...

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Saturday, September 12

Featured

Cape Ann Pride's Fall Masquerade Ball

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7:00 PM

Castle Hill on the Crane Estate, 290 Argilla Rd, Ipswich, MA

We're thrilled to invite you to Cape Ann Pride's Fall Masquerade Ball — our biggest event of the year, and a night we can't...

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Featured

Paul D'Angelo's 3rd Annual So-Long-To-Summer Comedy Show

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12

8:00 PM

The Cut - Stage • Studio • Restaurant • Bar, 177 Main St, Gloucester, MA

Besides headlining A-List comedy clubs for almost forty years, Paul has also opened for over sixty internationally known...

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Thursday, September 17

Featured

Tanya Donelly

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8:00 PM

The Cut - Stage • Studio • Restaurant • Bar, 177 Main St, Gloucester, MA

Tanya Donelly first emerged in the indie-rock landscape in the early 1980s, co-founding Throwing Muses (with stepsister Kristin...

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Friday, September 11

• A Band of Brothers - Not Just an Allman Brothers Tribute 8:00 pm

  The Cut - Stage • Studio • Restaurant • Bar, 177 Main St, Gloucester

  
  
• 2026 Art Auction: Call for Artists: Registration Deadline 9:00 am

  Sawyer Free Library, 2 Dale Ave, Gloucester

  
  

Saturday, September 12

• Cape Ann Pride's Fall Masquerade Ball 7:00 pm

  Castle Hill on the Crane Estate, 290 Argilla Rd, Ipswich

  
  
• Paul D'Angelo's 3rd Annual So-Long-To-Summer Comedy Show 8:00 pm

  The Cut - Stage • Studio • Restaurant • Bar, 177 Main St, Gloucester

  
  

Thursday, September 17

• Tanya Donelly 8:00 pm

  The Cut - Stage • Studio • Restaurant • Bar, 177 Main St, Gloucester

  
  
• Bring Your Friends to a Fun Free Introduction to Modern Square Dancing 7:00 pm

  Middleton Community Church, 66 Maple St, Middleton

  
  

Friday, September 18

• Dead to the Core - September Show 8:00 pm

  The Cut - Stage • Studio • Restaurant • Bar, 177 Main St, Gloucester

  
  

Saturday, September 19

• Thrift Haul - 50% off Everything 10:00 am

  Beverly Bootstraps Thrift Shop, 198 Rantoul St, Beverly

  
  
• Anthony Gomes – Praise Out Loud 2026 Tour 8:00 pm

  Larcom Theatre, 13 Wallis St, Beverly

  
  
• Fortune - Vinyl Era Class Rock Tribute Band 8:00 pm

  The Cut - Stage • Studio • Restaurant • Bar, 177 Main St, Gloucester

  
  

Sunday, September 20

• Open House 11:00 am

  72 Grapevine Road, Wenham, MA

  
  
• Third World 7:30 pm

  The Cut - Stage • Studio • Restaurant • Bar, 177 Main St, Gloucester

  
  

Thursday, September 24

• Building Dreams Gala 6:00 pm

  Danvers

  
  

Saturday, September 26

• Ana Popovic with Danielle Miraglia 8:00 pm

  The Cut - Stage • Studio • Restaurant • Bar, 177 Main St, Gloucester

  
  

Sunday, September 27

• Cape Ann Cake Fest 2:00 pm

  Windhover Performing Arts Center 247 Granite St. Rockport, MA

  
  

Thursday, October 1

• Flamenkora 8:00 pm

  The Cut - Stage • Studio • Restaurant • Bar, 177 Main St, Gloucester

  
  

Saturday, October 3

• Dueling Pianos 8:00 pm

  The Cut - Stage • Studio • Restaurant • Bar, 177 Main St, Gloucester

  
  

Friday, October 9

• Grunge Fest - Alice In Chains and Stone Temple Pilots Tribute Night 8:00 pm

  The Cut - Stage • Studio • Restaurant • Bar, 177 Main St, Gloucester

  
  

Saturday, October 10

• Prince of Darkness – The Ultimate Ozzy Experience 8:00 pm

  Larcom Theatre, 13 Wallis St, Beverly

  
  

Sunday, October 11

• Jimmy Tingle: The "Radical" Middle- Why Would a Comedian Run for Office? Film Screening + Q&A 8:30 pm

  The Cut - Stage • Studio • Restaurant • Bar, 177 Main St, Gloucester