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Holiday events in Gloucester, MA

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Light Up the Night at Goddard School Charlestown St. Martin’s Lantern Parde
Tue, Nov 11, 4:30 PM
Charlestown · The Goddard School of Charlestown
Light Up the Night at Goddard School Charlestown St. Martin’s Lantern Parde
Tue, Nov 11, 4:30 PM
Charlestown · The Goddard School of Charlestown
2025 Medford Pumpkin Smash
Sat, Nov 1, 10:30 AM
South Medford · McGlynn Middle School
2025 Medford Pumpkin Smash
Sat, Nov 1, 10:30 AM
South Medford · McGlynn Middle School
Sales end soon
Mid-Autumn Festival Celebration – Saturday, 10/18
Saturday at 1:00 PM
North Cambridge · 2464 Massachusetts Ave
Sales end soon
Mid-Autumn Festival Celebration – Saturday, 10/18
Saturday at 1:00 PM
North Cambridge · 2464 Massachusetts Ave
Sales end soon
Fall Festival at Artisan Childcare Center
Wednesday at 4:30 PM
North Cambridge · 153 Alewife Brook Pkwy
Sales end soon
Fall Festival at Artisan Childcare Center
Wednesday at 4:30 PM
North Cambridge · 153 Alewife Brook Pkwy
Nightmare on Elm Street
Fri, Oct 31, 7:00 PM
Somerville · Elm Street Taproom
Nightmare on Elm Street
Fri, Oct 31, 7:00 PM
Somerville · Elm Street Taproom
A Pop Up for the Ghouls, Goblins, and Gremlins
Sun, Oct 26, 12:00 PM
Dorchester · Dorchester Brewing Company
A Pop Up for the Ghouls, Goblins, and Gremlins
Sun, Oct 26, 12:00 PM
Dorchester · Dorchester Brewing Company
Santa at the Bogs 2025
Sun, Dec 7, 12:00 PM
Massachusetts · Bensons Pond Cranberries and Barn
Santa at the Bogs 2025
Sun, Dec 7, 12:00 PM
Massachusetts · Bensons Pond Cranberries and Barn
Lenox Mercantile Holiday Pop-Up 2025
Sat, Dec 6, 11:00 AM
Back Bay · The Lenox Hotel
Lenox Mercantile Holiday Pop-Up 2025
Sat, Dec 6, 11:00 AM
Back Bay · The Lenox Hotel
Billerica 11th Annual Holiday Fair
Sun, Nov 30, 11:00 AM
The Pines · Billerica - Elks Lodge
Billerica 11th Annual Holiday Fair
Sun, Nov 30, 11:00 AM
The Pines · Billerica - Elks Lodge
7th Annual Boston Halloween Town
Fri, Oct 31, 3:30 PM
Dorchester · Unity Sports & Cultural Club
7th Annual Boston Halloween Town
Fri, Oct 31, 3:30 PM
Dorchester · Unity Sports & Cultural Club
Kids Holiday Craft Fair, 2025
Sat, Dec 13, 1:00 PM
Atlantic · Robbins Library
Kids Holiday Craft Fair, 2025
Sat, Dec 13, 1:00 PM
Atlantic · Robbins Library
Pine Village Fall Festival
Wed, Oct 29, 5:30 PM
Brighton · 402 Western Ave
Pine Village Fall Festival
Wed, Oct 29, 5:30 PM
Brighton · 402 Western Ave
Sales end soon
Halloween Hoot! in Brookline: SPOOKY FUN FOR ALL AGES
Saturday at 6:00 PM
Boylston Street · First Parish in Brookline
Sales end soon
Halloween Hoot! in Brookline: SPOOKY FUN FOR ALL AGES
Saturday at 6:00 PM
Boylston Street · First Parish in Brookline
Halloween Comicfest 2025
Sat, Oct 25, 10:00 AM
Bemis · 134 Main St
Halloween Comicfest 2025
Sat, Oct 25, 10:00 AM
Bemis · 134 Main St
Sales end soon
Flannel Fest Saturdays
Saturday at 1:00 PM + 1 more
Jamaica Plain · Samuel Adams Boston Brewery
Sales end soon
Flannel Fest Saturdays
Saturday at 1:00 PM + 1 more
Jamaica Plain · Samuel Adams Boston Brewery
CSNDC Holiday Market & Craft Fair
Fri, Dec 5, 4:00 PM + 1 more
Dorchester · The Great Hall at Codman Square Health Center
CSNDC Holiday Market & Craft Fair
Fri, Dec 5, 4:00 PM + 1 more
Dorchester · The Great Hall at Codman Square Health Center
Waltham 3rd Annual Holiday Fair
Sat, Nov 29, 11:00 AM
Clematis Brook Station · American Legion
Waltham 3rd Annual Holiday Fair
Sat, Nov 29, 11:00 AM
Clematis Brook Station · American Legion
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
Zorvino Vineyards Holiday Sip & Shop
Sun, Nov 30, 11:00 AM
New Hampshire · Zorvino Vineyards
Zorvino Vineyards Holiday Sip & Shop
Sun, Nov 30, 11:00 AM
New Hampshire · Zorvino Vineyards

Trends in Gloucester

Explore more trends

Frequently asked questions about Gloucester

What are the best festival events to attend?

According to Eventbrite, the best festival events are:

Light Up the Night at Goddard School Charlestown St. Martin’s Lantern Parde

2025 Medford Pumpkin Smash

Nightmare on Elm Street

A Pop Up for the Ghouls, Goblins, and Gremlins

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:

Fall Festival at Artisan Childcare Center

Mid-Autumn Festival Celebration – Saturday, 10/18

Flannel Fest Saturdays

Halloween Hoot! in Brookline: SPOOKY FUN FOR ALL AGES

Light Up the Night at Goddard School Charlestown St. Martin’s Lantern Parde

Light Up the Night at Goddard School Charlestown St. Martin’s Lantern Parde

2025 Medford Pumpkin Smash

2025 Medford Pumpkin Smash

Mid-Autumn Festival Celebration – Saturday, 10/18

Mid-Autumn Festival Celebration – Saturday, 10/18

Fall Festival at Artisan Childcare Center

Fall Festival at Artisan Childcare Center

Nightmare on Elm Street

Nightmare on Elm Street

A Pop Up for the Ghouls, Goblins, and Gremlins

A Pop Up for the Ghouls, Goblins, and Gremlins

Santa at the Bogs 2025

Santa at the Bogs 2025

Lenox Mercantile Holiday Pop-Up 2025

Lenox Mercantile Holiday Pop-Up 2025

Billerica 11th Annual Holiday Fair

Billerica 11th Annual Holiday Fair

7th Annual Boston Halloween Town

7th Annual Boston Halloween Town

Kids Holiday Craft Fair, 2025

Kids Holiday Craft Fair, 2025

Pine Village Fall Festival

Pine Village Fall Festival

Halloween Hoot! in Brookline: SPOOKY FUN FOR ALL AGES

Halloween Hoot! in Brookline: SPOOKY FUN FOR ALL AGES

Halloween Comicfest 2025

Halloween Comicfest 2025

Flannel Fest Saturdays

Flannel Fest Saturdays

CSNDC Holiday Market & Craft Fair

CSNDC Holiday Market & Craft Fair

Waltham 3rd Annual Holiday Fair

Waltham 3rd Annual Holiday Fair

Solstice Fair Rates Days

Solstice Fair Rates Days

Solstice Fair Rates Day

Solstice Fair Rates Day

Zorvino Vineyards Holiday Sip & Shop

Zorvino Vineyards Holiday Sip & Shop

Things to do around Gloucester

Trends in Gloucester

1. Stage fort park

2. Beauport hotel

3. October

4. Live music

5. North shore happenings

6. Halloween

7. Fantasy ball

8. Kids events today

9. Job fair

10. Craft fairs

11. Singles events

12. Cape ann makers market sip and shop