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Holiday events
in Gloucester, MA

Discover the best Holiday events in your area and online

Holiday
Gloucester
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Hawthorne Hotel's 2026 Halloween Ball: Phobia primary image

Hawthorne Hotel's 2026 Halloween Ball: Phobia

Sat, Oct 24 • 7:30 PM

Hawthorne Hotel

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12th Annual Halloween Gala primary image

12th Annual Halloween Gala

Thu, Oct 22 • 6:30 PM

Willowdale Estate

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Colonial Hall's Annual Heaven & Hell Ball! primary image

Colonial Hall's Annual Heaven & Hell Ball!

Sat, Oct 24 • 8:00 PM

Colonial Hall at Rockafellas

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Autumn Breakfast 2026 primary image

Autumn Breakfast 2026

Thu, Oct 22 • 7:30 AM

Cruiseport Gloucester

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Haunted Speakeasy Salem primary image

Haunted Speakeasy Salem

Sat, Oct 24 • 6:00 PM

Hamilton Hall

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Longboards Upstairs Presents Monster Mash III primary image

Longboards Upstairs Presents Monster Mash III

Fri, Oct 30 • 8:00 PM

Longboards Restaurant & Bar

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Eerie Stories on Salem Sound primary image

Eerie Stories on Salem Sound

Today • 2:00 PM + 13 more

Central Wharf

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Beauport Hotel Presents: The Halloween Soirée primary image

Beauport Hotel Presents: The Halloween Soirée

Sat, Oct 31 • 8:00 PM

Beauport Hotel Gloucester

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