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Holiday events in Great Barrington, MA

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Sip & Shop Holiday Networking
Mon, Dec 8, 4:30 PM
Fiberloid · Mercedes-Benz of Springfield
Sip & Shop Holiday Networking
Mon, Dec 8, 4:30 PM
Fiberloid · Mercedes-Benz of Springfield
Make & Take Painting Project: Magical Christmas Tree
Sat, Dec 6, 2:00 PM
East Bristol · Bristol Public Library
Make & Take Painting Project: Magical Christmas Tree
Sat, Dec 6, 2:00 PM
East Bristol · Bristol Public Library
The 845 Fear Fest Costume Party
Fri, Oct 24, 8:00 PM
Pine Bush · Pine Bush
The 845 Fear Fest Costume Party
Fri, Oct 24, 8:00 PM
Pine Bush · Pine Bush
Just added!
St. Valentine's Day Tea
Sat, Feb 14, 2:00 PM
East Bristol · Bristol Public Library
Just added!
St. Valentine's Day Tea
Sat, Feb 14, 2:00 PM
East Bristol · Bristol Public Library
Halloween Trivia
Wed, Oct 29, 6:00 PM
East Bristol · Manross Memorial Library
Halloween Trivia
Wed, Oct 29, 6:00 PM
East Bristol · Manross Memorial Library
Sales end soon
“Sips, Spells & Strokes” — Halloween Paint & Sip Thursdays
Thursday at 6:00 PM + 7 more
Highwood · Weed's Cafe
Sales end soon
“Sips, Spells & Strokes” — Halloween Paint & Sip Thursdays
Thursday at 6:00 PM + 7 more
Highwood · Weed's Cafe
Creatures of the Night
Fri, Oct 17, 5:00 PM
Sherwood Manor · 138 N Maple St
Creatures of the Night
Fri, Oct 17, 5:00 PM
Sherwood Manor · 138 N Maple St
Frank Righetti Memorial Holiday Brunch & VSCCA AGM at West Point
Sun, Nov 9, 9:30 AM
Glenclyffe · The Thayer Hotel
Frank Righetti Memorial Holiday Brunch & VSCCA AGM at West Point
Sun, Nov 9, 9:30 AM
Glenclyffe · The Thayer Hotel
Selling quickly
20th Reunion for the Saratoga Springs High School Class of 2005
Saturday at 6:00 PM
Yaddo · Harvey's Restaurant and Bar
Selling quickly
20th Reunion for the Saratoga Springs High School Class of 2005
Saturday at 6:00 PM
Yaddo · Harvey's Restaurant and Bar
Free, Family Friendly Pumpkin Painting! Donations support Amherst Survival.
Sat, Oct 25, 11:00 AM
Factory Hollow · Mill District Local Art Gallery
Free, Family Friendly Pumpkin Painting! Donations support Amherst Survival.
Sat, Oct 25, 11:00 AM
Factory Hollow · Mill District Local Art Gallery
Mill District General Store & Local Art Gallery Annual Holiday Arts Market
Sat, Nov 8, 10:00 AM
Factory Hollow · Mill District Local Art Gallery
Mill District General Store & Local Art Gallery Annual Holiday Arts Market
Sat, Nov 8, 10:00 AM
Factory Hollow · Mill District Local Art Gallery
Lipstick & Laughter presents a Halloween Costume Comedy Show at Pub 34!
Sat, Oct 25, 7:30 PM
West River · 439 Derby Ave
Lipstick & Laughter presents a Halloween Costume Comedy Show at Pub 34!
Sat, Oct 25, 7:30 PM
West River · 439 Derby Ave
CRAWL-O-WEEN '25: Connecticut's #1 Halloween Bar Crawl
Sat, Oct 25, 12:00 PM
Downtown · 15+ Exclusive Bars & Club - Downtown New Haven
CRAWL-O-WEEN '25: Connecticut's #1 Halloween Bar Crawl
Sat, Oct 25, 12:00 PM
Downtown · 15+ Exclusive Bars & Club - Downtown New Haven
Fright Night Trivia
Fri, Oct 31, 6:00 PM
Hazardville · Powder Hollow Brewery
Fright Night Trivia
Fri, Oct 31, 6:00 PM
Hazardville · Powder Hollow Brewery
Powder Hollow's 4th Annual Hollow-Ween Party
Sat, Oct 25, 6:00 PM
Hazardville · Powder Hollow Brewery
Powder Hollow's 4th Annual Hollow-Ween Party
Sat, Oct 25, 6:00 PM
Hazardville · Powder Hollow Brewery
New Haven's Best Halloween Weekend Bar Crawl
Downtown · Best Bars in New Haven
New Haven's Best Halloween Weekend Bar Crawl
Downtown · Best Bars in New Haven
DJ King Bully's Halloween Party
Sat, Nov 1, 10:00 PM
Yaddo · Putnam Place
DJ King Bully's Halloween Party
Sat, Nov 1, 10:00 PM
Yaddo · Putnam Place
New Haven Halloween Bar Crawl
Sat, Oct 25, 4:00 PM
Downtown · Prime 16
New Haven Halloween Bar Crawl
Sat, Oct 25, 4:00 PM
Downtown · Prime 16
Spooktacular Oktoberfest
Sat, Oct 25, 1:00 PM
Boutonville · Trailside Nature Museum
Spooktacular Oktoberfest
Sat, Oct 25, 1:00 PM
Boutonville · Trailside Nature Museum
2025 New Haven Halloween Bar Crawl
Sat, Nov 1, 4:00 PM
Downtown · Prime 16
2025 New Haven Halloween Bar Crawl
Sat, Nov 1, 4:00 PM
Downtown · Prime 16

Trends in Great Barrington

Explore more trends

Frequently asked questions about Great Barrington

What are the best events to attend?

According to Eventbrite, the best events are:

Sip & Shop Holiday Networking

Make & Take Painting Project: Magical Christmas Tree

St. Valentine's Day Tea

Halloween Trivia

Which events are currently trending in Great Barrington?

The trending searches this month in Great Barrington are:

oktoberfest in berkshires

craft fairs

live music

car show

Which events are coming up?

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

“Sips, Spells & Strokes” — Halloween Paint & Sip Thursdays

20th Reunion for the Saratoga Springs High School Class of 2005

Creatures of the Night

The 845 Fear Fest Costume Party

Sip & Shop Holiday Networking

Sip & Shop Holiday Networking

Make & Take Painting Project: Magical Christmas Tree

Make & Take Painting Project: Magical Christmas Tree

The 845 Fear Fest Costume Party

The 845 Fear Fest Costume Party

St. Valentine's Day Tea

St. Valentine's Day Tea

Halloween Trivia

Halloween Trivia

“Sips, Spells & Strokes” — Halloween Paint & Sip Thursdays

“Sips, Spells & Strokes” — Halloween Paint & Sip Thursdays

Creatures of the Night

Creatures of the Night

Frank Righetti Memorial Holiday Brunch & VSCCA AGM at West Point

Frank Righetti Memorial Holiday Brunch & VSCCA AGM at West Point

20th Reunion for the Saratoga Springs High School Class of 2005

20th Reunion for the Saratoga Springs High School Class of 2005

Free, Family Friendly Pumpkin Painting! Donations support Amherst Survival.

Free, Family Friendly Pumpkin Painting! Donations support Amherst Survival.

Mill District General Store & Local Art Gallery Annual Holiday Arts Market

Mill District General Store & Local Art Gallery Annual Holiday Arts Market

Lipstick & Laughter presents a Halloween Costume Comedy Show at Pub 34!

Lipstick & Laughter presents a Halloween Costume Comedy Show at Pub 34!

CRAWL-O-WEEN '25: Connecticut's #1 Halloween Bar Crawl

CRAWL-O-WEEN '25: Connecticut's #1 Halloween Bar Crawl

Fright Night Trivia

Fright Night Trivia

Powder Hollow's 4th Annual Hollow-Ween Party

Powder Hollow's 4th Annual Hollow-Ween Party

New Haven's Best Halloween Weekend Bar Crawl

New Haven's Best Halloween Weekend Bar Crawl

DJ King Bully's Halloween Party

DJ King Bully's Halloween Party

New Haven Halloween Bar Crawl

New Haven Halloween Bar Crawl

Spooktacular Oktoberfest

Spooktacular Oktoberfest

2025 New Haven Halloween Bar Crawl

2025 New Haven Halloween Bar Crawl

Things to do around Great Barrington

Trends in Great Barrington

1. Oktoberfest in berkshires

2. Craft fairs

3. Live music

4. Car show

5. Halloween

6. Great barrington harvest fest

7. Autumn

8. Christmas

9. Open mic

10. New years eve party in southern berkshires

11. Trivia

12. Speed dating events