Holiday events in Gloucester, MA

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

Ipswich Ale Brewery Oktoberfest
Fri, Sep 19, 7:30 PM
Ipswich · Ipswich Ale Brewery
Ipswich Ale Brewery Oktoberfest
Fri, Sep 19, 7:30 PM
Ipswich · Ipswich Ale Brewery
Sales end soon
Prelude To Carnival (Friday August 22nd, 2025)
Friday at 10:00 PM
Downtown · Hava Nightclub
Sales end soon
Prelude To Carnival (Friday August 22nd, 2025)
Friday at 10:00 PM
Downtown · Hava Nightclub
Hocus Pocus Pumpkin Fest
Thu, Oct 23, 6:00 PM
Cluffs Crossing · 99 Rockingham Park Blvd
Hocus Pocus Pumpkin Fest
Thu, Oct 23, 6:00 PM
Cluffs Crossing · 99 Rockingham Park Blvd
Dickens Festival Holiday Craft Fair Artisan Application
Sat, Nov 22, 10:00 AM
South Quincy · All Souls Church
Dickens Festival Holiday Craft Fair Artisan Application
Sat, Nov 22, 10:00 AM
South Quincy · All Souls Church
The Mid-Autumn Lantern Festival 2025
Fri, Aug 29, 5:00 PM + 2 more
Downtown · Zapatos Ice Skaing Arena
The Mid-Autumn Lantern Festival 2025
Fri, Aug 29, 5:00 PM + 2 more
Downtown · Zapatos Ice Skaing Arena
Marlborough's Oktoberfest
Sat, Sep 27, 1:00 PM
Downtown · Flying Dreams Parking Lot
Marlborough's Oktoberfest
Sat, Sep 27, 1:00 PM
Downtown · Flying Dreams Parking Lot
Spirit of Christmas
Sat, Nov 22, 7:00 PM
Downtown · -Governor's Inn & Restaurant
Spirit of Christmas
Sat, Nov 22, 7:00 PM
Downtown · -Governor's Inn & Restaurant
Lin' On Luck at Rockport Harvest Fest
Sat, Oct 18, 11:00 AM
Lands End · Dock Square
Lin' On Luck at Rockport Harvest Fest
Sat, Oct 18, 11:00 AM
Lands End · Dock Square
Fall Craft Fair
Sat, Oct 4, 12:00 PM
Everett · Samuel Gentile Recreation Center
Fall Craft Fair
Sat, Oct 4, 12:00 PM
Everett · Samuel Gentile Recreation Center
3rd Annual Harvest Fest
Sat, Sep 13, 11:00 AM
South Lawrence · Riverfront State Park
3rd Annual Harvest Fest
Sat, Sep 13, 11:00 AM
South Lawrence · Riverfront State Park
Boston Landing Fall Crawl
Sat, Sep 20, 11:00 AM
Brighton · Boston Landing
Boston Landing Fall Crawl
Sat, Sep 20, 11:00 AM
Brighton · Boston Landing
Solstice Fair Rates Days
Sat, Jun 20, 12:00 PM
Salem Depot · Healing Power of Flowers
Solstice Fair Rates Days
Sat, Jun 20, 12:00 PM
Salem Depot · Healing Power of Flowers
Solstice Fair Rates Day
Sun, Jun 21, 12:00 PM
Salem Depot · Healing Power of Flowers
Solstice Fair Rates Day
Sun, Jun 21, 12:00 PM
Salem Depot · Healing Power of Flowers
Halloween Psychic Faire & Vendor Market
Sat, Oct 4, 11:00 AM
Collinsville · Moonlight & Mindfulness
Halloween Psychic Faire & Vendor Market
Sat, Oct 4, 11:00 AM
Collinsville · Moonlight & Mindfulness
Fall Festival Craft & Vendor Fair
Sun, Nov 9, 10:00 AM
Massachusetts · American Legion Post 313
Fall Festival Craft & Vendor Fair
Sun, Nov 9, 10:00 AM
Massachusetts · American Legion Post 313
Biddeford Oktoberfest
Sat, Sep 27, 12:00 PM + 1 more
Five Points · Pearl Street
Biddeford Oktoberfest
Sat, Sep 27, 12:00 PM + 1 more
Five Points · Pearl Street
Gray Gables Gals, Inc. 5th Annual Witches Walk
Sat, Oct 18, 4:00 PM
Mashnee Island · Gray Gables Beach
Gray Gables Gals, Inc. 5th Annual Witches Walk
Sat, Oct 18, 4:00 PM
Mashnee Island · Gray Gables Beach
Ocean State Artisans 34th Annual Holiday Market & Food Drive
Fri, Nov 28, 9:00 AM + 2 more
Saylesville Highlands · Bally's Twin River Lincoln
Ocean State Artisans 34th Annual Holiday Market & Food Drive
Fri, Nov 28, 9:00 AM + 2 more
Saylesville Highlands · Bally's Twin River Lincoln
Holly Daze Craft Fair
Sat, Nov 1, 9:00 AM
Somersworth · First Parish United Church of Christ
Holly Daze Craft Fair
Sat, Nov 1, 9:00 AM
Somersworth · First Parish United Church of Christ
Halloween Haunt - SK Pierce Haunted Mansion-Gardner MA
Sat, Sep 27, 5:45 PM
South Gardner · SK Haunted Victorian Mansion
Halloween Haunt - SK Pierce Haunted Mansion-Gardner MA
Sat, Sep 27, 5:45 PM
South Gardner · SK Haunted Victorian Mansion

Trends in Gloucester

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Frequently asked questions about Gloucester

What are the best festival events to attend?

According to Eventbrite, the best festival events are:

Hocus Pocus Pumpkin Fest

Dickens Festival Holiday Craft Fair Artisan Application

Marlborough's Oktoberfest

Spirit of Christmas

Which events are currently trending in Gloucester?

The trending searches this month in Gloucester are:

Which festival events are coming up?

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

Prelude To Carnival (Friday August 22nd, 2025)

The Mid-Autumn Lantern Festival 2025

3rd Annual Harvest Fest

Ipswich Ale Brewery Oktoberfest

Ipswich Ale Brewery Oktoberfest

Ipswich Ale Brewery Oktoberfest

Prelude To Carnival (Friday August 22nd, 2025)

Prelude To Carnival (Friday August 22nd, 2025)

Hocus Pocus Pumpkin Fest

Hocus Pocus Pumpkin Fest

Dickens Festival Holiday Craft Fair Artisan Application

Dickens Festival Holiday Craft Fair Artisan Application

The Mid-Autumn Lantern Festival 2025

The Mid-Autumn Lantern Festival 2025

Marlborough's Oktoberfest

Marlborough's Oktoberfest

Spirit of Christmas

Spirit of Christmas

Lin' On Luck at Rockport Harvest Fest

Lin' On Luck at Rockport Harvest Fest

Fall Craft Fair

Fall Craft Fair

3rd Annual Harvest Fest

3rd Annual Harvest Fest

Boston Landing Fall Crawl

Boston Landing Fall Crawl

Solstice Fair Rates Days

Solstice Fair Rates Days

Solstice Fair Rates Day

Solstice Fair Rates Day

Halloween Psychic Faire & Vendor Market

Halloween Psychic Faire & Vendor Market

Fall Festival Craft & Vendor Fair

Fall Festival Craft & Vendor Fair

Biddeford Oktoberfest

Biddeford Oktoberfest

Gray Gables Gals, Inc. 5th Annual Witches Walk

Gray Gables Gals, Inc. 5th Annual Witches Walk

Ocean State Artisans 34th Annual Holiday Market & Food Drive

Ocean State Artisans 34th Annual Holiday Market & Food Drive

Holly Daze Craft Fair

Holly Daze Craft Fair

Halloween Haunt - SK Pierce Haunted Mansion-Gardner MA

Halloween Haunt - SK Pierce Haunted Mansion-Gardner MA

Things to do around Gloucester

Trends in Gloucester

1. Beauport hotel

2. Stage fort park

3. Live music

4. Birdseye rooftop

5. Rooftop party beauport hotel

6. Beauport

7. North shore happenings

8. Fantasy ball

9. Outdoor concert

10. Beauport hotel and rooftop pool

11. Reggae cruise

12. Beauport hotel annie brobst