Community Events and Things to do in Gloucester, MA this month

Search for something you love or check out popular events in your area.

Going fast
The WBUR Festival
Boston · Boston University
Going fast
The WBUR Festival
Boston · Boston University
Going fast
Plant Bingo @ Castle Island South Boston
Wednesday at 6:00 PM
Boston · Castle Island Brewing - South Boston
Going fast
Plant Bingo @ Castle Island South Boston
Wednesday at 6:00 PM
Boston · Castle Island Brewing - South Boston
Golden Affair - 1Year Anniversary Event
Today at 4:00 PM
Cambridge · La Fabrica
Golden Affair - 1Year Anniversary Event
Today at 4:00 PM
Cambridge · La Fabrica
Going fast
May 24th , 2026 - Drag Me To Bunch @ Carrie Nation
Sun, May 24, 12:00 PM
Boston · Carrie Nation Cocktail Club
Going fast
May 24th , 2026 - Drag Me To Bunch @ Carrie Nation
Sun, May 24, 12:00 PM
Boston · Carrie Nation Cocktail Club
Wetland— On Black Poetics and Water presented by Porsha Olayiwola
Sun, May 31, 4:00 PM
Cambridge · Western Avenue Baptist Church
Wetland— On Black Poetics and Water presented by Porsha Olayiwola
Sun, May 31, 4:00 PM
Cambridge · Western Avenue Baptist Church
May 31st , 2026 - Drag Me To Bunch @ Carrie Nation
Sun, May 31, 12:00 PM
Boston · Carrie Nation Cocktail Club
May 31st , 2026 - Drag Me To Bunch @ Carrie Nation
Sun, May 31, 12:00 PM
Boston · Carrie Nation Cocktail Club
Sales end soon
Battle of Bunker Hill Tour
Thursday at 11:00 AM + 3 more
Boston · Atlantic Avenue/ Milk Street
Sales end soon
Battle of Bunker Hill Tour
Thursday at 11:00 AM + 3 more
Boston · Atlantic Avenue/ Milk Street
Sales end soon
Crime Tour 2026 Boston Detective Tours
Thursday at 1:00 PM + 3 more
Boston · Atlantic Avenue/ Milk Street
Sales end soon
Crime Tour 2026 Boston Detective Tours
Thursday at 1:00 PM + 3 more
Boston · Atlantic Avenue/ Milk Street
IT’S GIVING: MASQUERADE BALL
Sat, May 30, 10:00 PM
Cambridge · Descent
IT’S GIVING: MASQUERADE BALL
Sat, May 30, 10:00 PM
Cambridge · Descent
Sales end soon
Love The Fenway — Ten Together
Thursday at 6:00 PM
Boston · Eastern Standard
Sales end soon
Love The Fenway — Ten Together
Thursday at 6:00 PM
Boston · Eastern Standard
Boston 101 History Tour
Sat, May 23, 11:00 AM + 1 more
Boston · Park Street & Tremont Street
Boston 101 History Tour
Sat, May 23, 11:00 AM + 1 more
Boston · Park Street & Tremont Street
Boston Witchcraft Tour
Sat, May 23, 1:00 PM + 1 more
Boston · Park Street & Tremont Street
Boston Witchcraft Tour
Sat, May 23, 1:00 PM + 1 more
Boston · Park Street & Tremont Street
Almost full
Millennial Speed-Dating (Monogamous)
Sat, May 30, 7:00 PM
Boston · Mighty Squirrel Taproom & Kitchen
Almost full
Millennial Speed-Dating (Monogamous)
Sat, May 30, 7:00 PM
Boston · Mighty Squirrel Taproom & Kitchen
The Third Annual Big Queer Boston Talent Show
Thu, May 28, 8:00 PM
Boston · Jacques' Cabaret
The Third Annual Big Queer Boston Talent Show
Thu, May 28, 8:00 PM
Boston · Jacques' Cabaret
South Shore Speed Dating! Ages 29-39
Thu, May 28, 6:30 PM
Quincy · Break Rock Brewing
South Shore Speed Dating! Ages 29-39
Thu, May 28, 6:30 PM
Quincy · Break Rock Brewing
LinkUP Thursday
Thursday at 10:30 PM + 1 more
Boston · Hava Nightclub
LinkUP Thursday
Thursday at 10:30 PM + 1 more
Boston · Hava Nightclub
ROXBURY ROOTS
Sat, May 30, 6:00 PM
Boston · Hibernian Hall
ROXBURY ROOTS
Sat, May 30, 6:00 PM
Boston · Hibernian Hall
Matcha + Meetup: Cambridge
Sat, May 23, 12:00 PM
Cambridge · Cafe of the Day
Matcha + Meetup: Cambridge
Sat, May 23, 12:00 PM
Cambridge · Cafe of the Day
TQNC Queer Art Market
Sun, May 31, 12:30 PM
Boston · Artisan's Asylum
TQNC Queer Art Market
Sun, May 31, 12:30 PM
Boston · Artisan's Asylum
Community Collage - An Experiment in Collective Seeing
Thursday at 6:00 PM
Cambridge · Still Life Studios
Community Collage - An Experiment in Collective Seeing
Thursday at 6:00 PM
Cambridge · Still Life Studios

Trends in Gloucester

Explore more trends

Frequently asked questions about Gloucester

What are the best events to attend this month?

According to Eventbrite, the best events this month are:

The WBUR Festival

May 24th , 2026 - Drag Me To Bunch @ Carrie Nation

Wetland— On Black Poetics and Water presented by Porsha Olayiwola

May 31st , 2026 - Drag Me To Bunch @ Carrie Nation

Which events are currently trending in Gloucester?

The trending searches this month in Gloucester are:

mothers day

singles events

north shore happenings

comedy

Which events are coming up?

Discover the best events happening soon – you don't want to miss them:

Golden Affair - 1Year Anniversary Event

Plant Bingo @ Castle Island South Boston

Battle of Bunker Hill Tour

Crime Tour 2026 Boston Detective Tours

The WBUR Festival

The WBUR Festival

Plant Bingo @ Castle Island South Boston

Plant Bingo @ Castle Island South Boston

Golden Affair - 1Year Anniversary Event

Golden Affair - 1Year Anniversary Event

May 24th , 2026 - Drag Me To Bunch @ Carrie Nation

May 24th , 2026 - Drag Me To Bunch @ Carrie Nation

Wetland— On Black Poetics and Water presented by Porsha Olayiwola

Wetland— On Black Poetics and Water presented by Porsha Olayiwola

May 31st , 2026 - Drag Me To Bunch @ Carrie Nation

May 31st , 2026 - Drag Me To Bunch @ Carrie Nation

Battle of Bunker Hill Tour

Battle of Bunker Hill Tour

Crime Tour 2026 Boston Detective Tours

Crime Tour 2026 Boston Detective Tours

IT’S GIVING: MASQUERADE BALL

IT’S GIVING: MASQUERADE BALL

Love The Fenway — Ten Together

Love The Fenway — Ten Together

Boston 101 History Tour

Boston 101 History Tour

Boston Witchcraft Tour

Boston Witchcraft Tour

Millennial Speed-Dating (Monogamous)

Millennial Speed-Dating (Monogamous)

The Third Annual Big Queer Boston Talent Show

The Third Annual Big Queer Boston Talent Show

South Shore Speed Dating! Ages 29-39

South Shore Speed Dating! Ages 29-39

LinkUP Thursday

LinkUP Thursday

ROXBURY ROOTS

ROXBURY ROOTS

Matcha + Meetup: Cambridge

Matcha + Meetup: Cambridge

TQNC Queer Art Market

TQNC Queer Art Market

Community Collage - An Experiment in Collective Seeing

Community Collage - An Experiment in Collective Seeing

Things to do around Gloucester

Trends in Gloucester

1. Mothers day

2. Singles events

3. North shore happenings

4. Comedy

5. Memorial day weekend events

6. Kids events today

7. Speed dating

8. Fantasy ball

9. May events

10. Live music

11. Beauport hotel gloucester

12. Rooftop party beauport hotel

What are the best events to attend this month?

Which events are currently trending in Gloucester?

Which events are coming up?