Live Events in Gloucester, Massachusetts

Gloucester, Massachusetts has 20 venues with upcoming events — museum, gallery and restaurant. 235 events are on the calendar, at spots like The Rhumb Line Bar & Restaurant, Cape Ann Lanes/Laneside Pub & Brewery, Cape Ann Museum (CAM).

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This Weekend in Gloucester

Bluegrass night with Joe Wilkins

The Rhumb Line Bar & Restaurant

Tue, Oct 6 · 7:30 PM

Music Video Bingo

Cape Ann Lanes/Laneside Pub & Brewery

Tue, Oct 6 · 7:30 PM

Robert Russo at BankGloucester

North Shore Arts Association

Tue, Oct 6

A Deeper Relationship with Painting and Drawing Workshop with Loren Doucette

The Cultural Center at Rocky Neck

Tue, Oct 6

CAM Studio Art: Design and Print the Folly Cove Way

Cape Ann Museum (CAM)

Wed, Oct 7 · 1:00 PM

Public Sail

Maritime Heritage Charters

Wed, Oct 7 · 2:30 PM

Community Night - GHS Girls Volleyball (20% of food sales donated)

Machaca

Wed, Oct 7 · 4:30 PM

Matt Rich & Guest

The Rhumb Line Bar & Restaurant

Wed, Oct 7 · 7:00 PM

Open Studio $15 09:30 AM to 12:30 PM

Snug Harbor Studio

Thu, Oct 8 · 10:09 AM

Harbor Stories Writers Workshop

Maritime Gloucester

Thu, Oct 8 · 5:00 PM

Dave Sags Blues Party

The Rhumb Line Bar & Restaurant

Thu, Oct 8 · 7:30 PM

Nervous Guys | G Gordon Gritty | The Chip Rockers | Beware the Dangers of a Ghost Scorpion

The Cut - Stage • Studio • Restaurant • Bar

Thu, Oct 8 · 8:00 PM

Cape Ann Plein Air

North Shore Arts Association

Thu, Oct 8

Line Dancing with Elizabeth Reed ($15)

Snug Harbor Studio

Fri, Oct 9 · 9:00 AM

Captain Elias Davis House Tour

Cape Ann Museum (CAM)

Fri, Oct 9 · 2:00 PM

John Jerome

The Rhumb Line Bar & Restaurant

Fri, Oct 9 · 5:30 PM

Cosmic Bowling

Cape Ann Lanes/Laneside Pub & Brewery

Fri, Oct 9 · 6:00 PM

Grunge Fest @ The Cut! Alice In Chains and Stone Temple Pilots Tribute Night (Nutshell & Stone Temple Posers)

The Cut - Stage • Studio • Restaurant • Bar

Fri, Oct 9 · 8:00 PM

Skunk Sessions

The Rhumb Line Bar & Restaurant

Fri, Oct 9 · 8:30 PM

Tregony Bow

The Rhumb Line Bar & Restaurant

Fri, Oct 9 · 8:30 PM

Coming Up in Gloucester

Fall Leagues — Men's League start

Harbor 9 Golf & Sports Bar

Mon, Oct 12 · 6:00 AM

Cape Ann Studio Tour

Melody Phaneuf Paintings

Mon, Oct 12 · 10:00 AM

Bradley Royds & Eric Reardon

The Rhumb Line Bar & Restaurant

Mon, Oct 12 · 6:00 PM

Books and Brews

Cape Ann Lanes/Laneside Pub & Brewery

Mon, Oct 12

Skill Building Open Air Nans 8 Rowe Ave Rockport

Snug Harbor Studio

Tue, Oct 13 · 10:00 AM

Music Video Bingo

Cape Ann Lanes/Laneside Pub & Brewery

Tue, Oct 13 · 7:30 PM

Bluegrass night with Joe Wilkins

The Rhumb Line Bar & Restaurant

Tue, Oct 13 · 7:30 PM

Fall Leagues — Women's League start

Harbor 9 Golf & Sports Bar

Wed, Oct 14 · 6:30 AM

Matt Rich & Guest

The Rhumb Line Bar & Restaurant

Wed, Oct 14 · 7:00 PM

Dave Sags Blues Party

The Rhumb Line Bar & Restaurant

Thu, Oct 15 · 7:30 PM

John Marshall at the Beauport Hotel

North Shore Arts Association

Thu, Oct 15

Line Dancing with Elizabeth Reed ($15)

Snug Harbor Studio

Fri, Oct 16 · 9:00 AM

Captain Elias Davis House Tour

Cape Ann Museum (CAM)

Fri, Oct 16 · 2:00 PM

Johnny Carwash

The Rhumb Line Bar & Restaurant

Fri, Oct 16 · 5:30 PM

Cosmic Bowling

Cape Ann Lanes/Laneside Pub & Brewery

Fri, Oct 16 · 6:00 PM

Reckoners with Kevin James Graham

The Cut - Stage • Studio • Restaurant • Bar

Fri, Oct 16 · 8:00 PM

Tregony Bow

The Rhumb Line Bar & Restaurant

Fri, Oct 16 · 8:30 PM

The Mike McGoewn Band

The Rhumb Line Bar & Restaurant

Fri, Oct 16 · 8:30 PM

“Brave-Too-Much”: The Legend of John Coffee Hays Curator’s Remarks & Exhibit Preview

Hammond Castle Museum

Fri, Oct 16

HEADLANDS

The Rhumb Line Bar & Restaurant

Sat, Oct 17 · 5:00 PM

Allen Estes & Mike O'Connell

The Rhumb Line Bar & Restaurant

Sat, Oct 17 · 5:30 PM

Chelsea Berry - Peace Soldier Album Release

The Cut - Stage • Studio • Restaurant • Bar

Sat, Oct 17 · 7:00 PM

Dire Wolf

The Rhumb Line Bar & Restaurant

Sat, Oct 17 · 8:30 PM

Skunk Sessions

The Rhumb Line Bar & Restaurant

Sat, Oct 17 · 9:00 PM

Synergy 2026

North Shore Arts Association

Sat, Oct 17

Fall & Early Winter Temporary Exhibition: “Brave-Too-Much”: The Legend of John Coffee Hays

Hammond Castle Museum

Sat, Oct 17

Shubalananda Kirtan Sat Oct 17th

Floating Lotus Gloucester

Sat, Oct 17

Associate Small Works Show

North Shore Arts Association

Sat, Oct 17

Walking Tour: Historic Dogtown – A Walk Back in Time

Cape Ann Museum (CAM)

Sun, Oct 18 · 10:00 AM

The Gong Show

Movement Arts Gloucester MA

Sun, Oct 18 · 5:00 PM

The Bordellos

The Rhumb Line Bar & Restaurant

Sun, Oct 18 · 5:30 PM

Headlands Acoustic Trio

The Rhumb Line Bar & Restaurant

Mon, Oct 19 · 6:00 PM

Bradley Royds & Guest

The Rhumb Line Bar & Restaurant

Mon, Oct 19 · 6:00 PM

Books and Brews

Cape Ann Lanes/Laneside Pub & Brewery

Mon, Oct 19

Skill Building Open Air Ingrids 88 Walnut So Hamilton Lynn Maguire

Snug Harbor Studio

Tue, Oct 20 · 10:00 AM

Book Group meeting

Gloucester Unitarian Universalist Church

Tue, Oct 20 · 3:00 PM

Music Video Bingo

Cape Ann Lanes/Laneside Pub & Brewery

Tue, Oct 20 · 7:30 PM

Bluegrass night with Joe Wilkins

The Rhumb Line Bar & Restaurant

Tue, Oct 20 · 7:30 PM

Community Night - West Parish PTO

Machaca

Wed, Oct 21 · 4:30 PM

Matt Rich & Guest

The Rhumb Line Bar & Restaurant

Wed, Oct 21 · 7:00 PM

Venues in Gloucester (20)

The Rhumb Line Bar & RestaurantBar & Pub

110 events

Cape Ann Lanes/Laneside Pub & BreweryBowling alley

33 events

Cape Ann Museum (CAM)Museum

25 events

North Shore Arts AssociationGallery

9 events

The Cut - Stage • Studio • Restaurant • BarLive Music Venue

9 events

Hammond Castle MuseumMuseum

7 events

Snug Harbor Studio

7 events

Annisquam Village HallVillage hall

5 events

Harbor 9 Golf & Sports BarRestaurant

5 events

Cape Ann CruisesOutdoor Venue

4 events

The Cultural Center at Rocky NeckGallery

4 events

Cape Ann Art HavenArt school

3 events

MachacaRestaurant

3 events

Movement Arts Gloucester MADance school

3 events

Gloucester Unitarian Universalist ChurchChurch & House of Worship

2 events

Melody Phaneuf PaintingsGallery

2 events

Floating Lotus GloucesterBoutique

1 event

Maritime GloucesterMuseum

1 event

Maritime Heritage ChartersOutdoor Venue

1 event

Sargent House MuseumMuseum

1 event

Listings for Gloucester, Massachusetts are compiled from public sources, each named with the site it came from and dated with the last time we read it. Details can change — confirm with the venue before you go. How we collect & verify.