Events in Gloucester , Massachusetts

Cape Ann Farmers Market — Thursday

Thu, Sep 3Festival

Cape Ann Farmers Market — Thursday

Cape Ann Farmers Market

Gloucester, MA

Birdseye Rooftop Live Music Access

Beauport Hotel

Gloucester, MA

Birdseye Rooftop Live Music Access

Beauport Hotel

Gloucester, MA

Thu, Sep 3Art

Spiritualism Tours by Candlelight at Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Thu, Sep 3Art

Spiritualism Tours by Candlelight at Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Folk Week '26: Catherine Bent and Brasil Sonoroso

St. Anthony's by the Sea

Gloucester, MA

Folk Week '26: Catherine Bent and Brasil Sonoroso

St. Anthony's by the Sea

Gloucester, MA

ABRAXAS: New England's Premier Santana Tribute

The Cut

Gloucester, MA

ABRAXAS: New England's Premier Santana Tribute

The Cut

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Fri, Sep 4FREEArt

Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3

Cove Gallery

Gloucester, MA

Fri, Sep 4FREEArt

Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3

Cove Gallery

Gloucester, MA

Fri, Sep 4FREEMusic

Gloucester Block Party #3

Locations Vary

Gloucester, MA

Fri, Sep 4FREEMusic

Gloucester Block Party #3

Locations Vary

Gloucester, MA

Fri, Sep 4Nightlife

Sunset Sessions at the Birdseye Rooftop

Beauport Hotel

Gloucester, MA

Fri, Sep 4Nightlife

Sunset Sessions at the Birdseye Rooftop

Beauport Hotel

Gloucester, MA

Fri, Sep 4Music

Mighty Mystic with Double Tiger

The Cut

Gloucester, MA

Fri, Sep 4Music

Mighty Mystic with Double Tiger

The Cut

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

En Plein Air Sketch Classes with Sue Wheeler

Hammond Castle Museum

Gloucester, MA

En Plein Air Sketch Classes with Sue Wheeler

Hammond Castle Museum

Gloucester, MA

Sat, Sep 5Literary

Literary Gloucester, A Walking Tour

Gloucester Writers Center

Gloucester, MA

Sat, Sep 5Literary

Literary Gloucester, A Walking Tour

Gloucester Writers Center

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Street Stories with Phil Storey 2026

80 Main Antiques & Ephemera

Gloucester, MA

Street Stories with Phil Storey 2026

80 Main Antiques & Ephemera

Gloucester, MA

Sat, Sep 5FREEArt

Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3

Cove Gallery

Gloucester, MA

Sat, Sep 5FREEArt

Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3

Cove Gallery

Gloucester, MA

Sunset Sessions at the Birdseye Rooftop

Beauport Hotel

Gloucester, MA

Sunset Sessions at the Birdseye Rooftop

Beauport Hotel

Gloucester, MA

Birdseye Rooftop Sunset Sessions: Summer's Grand Finale Fireworks

Beauport Hotel

Gloucester, MA

Birdseye Rooftop Sunset Sessions: Summer's Grand Finale Fireworks

Beauport Hotel

Gloucester, MA

Folk Week '26: Henry Acker Trio

Movement Arts Gloucester MA

Gloucester, MA

Folk Week '26: Henry Acker Trio

Movement Arts Gloucester MA

Gloucester, MA

Sat, Sep 5Holiday

Beauport Cruiselines Labor Day Weekend Cruise

Beauport Cruiselines

Gloucester, MA

Sat, Sep 5Holiday

Beauport Cruiselines Labor Day Weekend Cruise

Beauport Cruiselines

Gloucester, MA

Barry Goudreau's Engine Room

The Cut

Gloucester, MA

Barry Goudreau's Engine Room

The Cut

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Sun, Sep 6Festival

Cape Ann Plein Air's Schooner Festival Paint Out

Stacey Boulevard

Gloucester, MA

Sun, Sep 6Festival

Cape Ann Plein Air's Schooner Festival Paint Out

Stacey Boulevard

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Sun, Sep 6FREEArt

Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3

Cove Gallery

Gloucester, MA

Sun, Sep 6FREEArt

Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3

Cove Gallery

Gloucester, MA

Sun, Sep 6Music

Folk Week '26: Ramon Tasat

St. Anthony's by the Sea

Gloucester, MA

Sun, Sep 6Music

Folk Week '26: Ramon Tasat

St. Anthony's by the Sea

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Mon, Sep 7FREEArt

Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3

Cove Gallery

Gloucester, MA

Mon, Sep 7FREEArt

Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3

Cove Gallery

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

The Backyard Growcery

Wed, Sep 9Community

The Backyard Growcery

Burnham's Field

Gloucester, MA

The Backyard Growcery

Wed, Sep 9Community

The Backyard Growcery

Burnham's Field

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Thu, Sep 10FREEArt

Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3

Cove Gallery

Gloucester, MA

Thu, Sep 10FREEArt

Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3

Cove Gallery

Gloucester, MA

En Plein Air Sketch Classes with Sue Wheeler

Hammond Castle Museum

Gloucester, MA

En Plein Air Sketch Classes with Sue Wheeler

Hammond Castle Museum

Gloucester, MA

Cape Ann Farmers Market — Thursday

Thu, Sep 10Festival

Cape Ann Farmers Market — Thursday

Cape Ann Farmers Market

Gloucester, MA

Cape Ann Farmers Market — Thursday

Thu, Sep 10Festival

Cape Ann Farmers Market — Thursday

Cape Ann Farmers Market

Gloucester, MA

Spiritualism Tours by Candlelight at Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Spiritualism Tours by Candlelight at Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Thu, Sep 10Community

The 11th Annual GrowDown

Oak to Ember

Gloucester, MA

Thu, Sep 10Community

The 11th Annual GrowDown

Oak to Ember

Gloucester, MA

Thu, Sep 10Literary

The Henry Tales!

Gloucester Writers Center

Gloucester, MA

Thu, Sep 10Literary

The Henry Tales!

Gloucester Writers Center

Gloucester, MA

Gloucester Stage Company presents MOON MAN WALK by James Ijames

Thu, Sep 10Theater

Gloucester Stage Company presents MOON MAN WALK by James Ijames

Gloucester Stage Company

Gloucester, MA

Gloucester Stage Company presents MOON MAN WALK by James Ijames

Thu, Sep 10Theater

Gloucester Stage Company presents MOON MAN WALK by James Ijames

Gloucester Stage Company

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Fri, Sep 11FREEArt

Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3

Cove Gallery

Gloucester, MA

Fri, Sep 11FREEArt

Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3

Cove Gallery

Gloucester, MA

Gloucester's Acropolis: Defining the City Then and Now

Gloucester's Acropolis: Defining the City Then and Now

Sawyer Free Library

Gloucester, MA

Gloucester's Acropolis: Defining the City Then and Now

Gloucester's Acropolis: Defining the City Then and Now

Sawyer Free Library

Gloucester, MA

Fri, Sep 11Family

Public Sail on a National Historic Landmark Schooner!

Schooner Adventure

Gloucester, MA

Fri, Sep 11Family

Public Sail on a National Historic Landmark Schooner!

Schooner Adventure

Gloucester, MA

Gloucester Stage Company presents MOON MAN WALK by James Ijames

Fri, Sep 11Theater

Gloucester Stage Company presents MOON MAN WALK by James Ijames

Gloucester Stage Company

Gloucester, MA

Gloucester Stage Company presents MOON MAN WALK by James Ijames

Fri, Sep 11Theater

Gloucester Stage Company presents MOON MAN WALK by James Ijames

Gloucester Stage Company

Gloucester, MA

Fri, Sep 11Music

A Band of Brothers – More than just and Allman Brothers Tribute

The Cut

Gloucester, MA

Fri, Sep 11Music

A Band of Brothers – More than just and Allman Brothers Tribute

The Cut

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Sat, Sep 12FREEArt

Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3

Cove Gallery

Gloucester, MA

Sat, Sep 12FREEArt

Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3

Cove Gallery

Gloucester, MA

Gloucester's Acropolis: Defining the City Then and Now

Gloucester's Acropolis: Defining the City Then and Now

Sawyer Free Library

Gloucester, MA

Gloucester's Acropolis: Defining the City Then and Now

Gloucester's Acropolis: Defining the City Then and Now

Sawyer Free Library

Gloucester, MA

Gloucester Stage Company presents MOON MAN WALK by James Ijames

Sat, Sep 12Theater

Gloucester Stage Company presents MOON MAN WALK by James Ijames

Gloucester Stage Company

Gloucester, MA

Gloucester Stage Company presents MOON MAN WALK by James Ijames

Sat, Sep 12Theater

Gloucester Stage Company presents MOON MAN WALK by James Ijames

Gloucester Stage Company

Gloucester, MA

Sat, Sep 12Comedy

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

The Cut

Gloucester, MA

Sat, Sep 12Comedy

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

The Cut

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Daily Guided & Self-Guided Tour of Hammond Castle Museum

Hammond Castle Museum

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Avery, Gottlieb & Rothko: By the Sea

Cape Ann Museum Downtown Campus

Gloucester, MA

Sun, Sep 13FREEArt

Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3

Cove Gallery

Gloucester, MA

Sun, Sep 13FREEArt

Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3

Cove Gallery

Gloucester, MA