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Holiday events in Great Barrington, MA

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Halloween Wicked Walk at Weis!
Fri, Oct 17, 6:30 PM + 15 more
Stonetown · The New Weis Center for Education, Arts & Recreation
Halloween Wicked Walk at Weis!
Fri, Oct 17, 6:30 PM + 15 more
Stonetown · The New Weis Center for Education, Arts & Recreation
Spooky Woods
Fri, Oct 24, 5:30 PM
Village of the Branch · Smithtown Historical Society
Spooky Woods
Fri, Oct 24, 5:30 PM
Village of the Branch · Smithtown Historical Society
Harvest Celebration and Passport Program North Fork Long Island
Fri, Nov 7, 6:00 PM
East Cutchogue · Raphael
Harvest Celebration and Passport Program North Fork Long Island
Fri, Nov 7, 6:00 PM
East Cutchogue · Raphael
Holiday Trail of Lights
Fri, Dec 5, 5:30 PM
Village of the Branch · Smithtown Historical Society
Holiday Trail of Lights
Fri, Dec 5, 5:30 PM
Village of the Branch · Smithtown Historical Society
Just added!
Creepy Crawly Animals and the Spirit of Halloween
Sat, Oct 25, 2:00 PM
Dolphin Cove · Innis Arden Cottage
Just added!
Creepy Crawly Animals and the Spirit of Halloween
Sat, Oct 25, 2:00 PM
Dolphin Cove · Innis Arden Cottage
Pop-up at Green Meadow Fall Fair
Sat, Oct 18, 10:00 AM
Upper Montvale · Green Meadow Waldorf School
Pop-up at Green Meadow Fall Fair
Sat, Oct 18, 10:00 AM
Upper Montvale · Green Meadow Waldorf School
Fall Fair
Sat, Oct 18, 10:00 AM
Upper Montvale · 307 Hungry Hollow Rd
Fall Fair
Sat, Oct 18, 10:00 AM
Upper Montvale · 307 Hungry Hollow Rd
Shrewsbury Holiday Craft and Vendor Fair
Sat, Dec 13, 11:00 AM
Great Brook Valley · Shrewsbury Sportsman Club
Shrewsbury Holiday Craft and Vendor Fair
Sat, Dec 13, 11:00 AM
Great Brook Valley · Shrewsbury Sportsman Club
Sales end soon
Holdridge's Hometown Fall Festival
Saturday at 10:00 AM
Connecticut · 749 Colonel Ledyard Hwy
Sales end soon
Holdridge's Hometown Fall Festival
Saturday at 10:00 AM
Connecticut · 749 Colonel Ledyard Hwy
St. Joseph Regional High School Craft Fair
Sun, Dec 7, 10:00 AM
Mount Pleasant · 40 Chestnut Ridge Rd
St. Joseph Regional High School Craft Fair
Sun, Dec 7, 10:00 AM
Mount Pleasant · 40 Chestnut Ridge Rd
Tice's Corner Fall Harvest Festival 2025
Sat, Oct 18, 10:00 AM
Mount Pleasant · Tice's Corner Marketplace
Tice's Corner Fall Harvest Festival 2025
Sat, Oct 18, 10:00 AM
Mount Pleasant · Tice's Corner Marketplace
Greater Ramsey Unico Italian Christmas Craft Fair
Sat, Nov 29, 10:00 AM
Fardale · 575 Darlington Ave
Greater Ramsey Unico Italian Christmas Craft Fair
Sat, Nov 29, 10:00 AM
Fardale · 575 Darlington Ave
Sales end soon
Hallock Homestead Annual Harvest Fest
Saturday at 10:00 AM
East Shoreham · Noah Hallock Homestead
Sales end soon
Hallock Homestead Annual Harvest Fest
Saturday at 10:00 AM
East Shoreham · Noah Hallock Homestead
Pumpkin Palooza at TLE Tuckahoe
Fri, Oct 24, 4:00 PM
Village of Tuckahoe · The Learning Experience - Tuckahoe
Pumpkin Palooza at TLE Tuckahoe
Fri, Oct 24, 4:00 PM
Village of Tuckahoe · The Learning Experience - Tuckahoe
Sales end soon
Harvest Fest Craft Fair & Antique Corner, Sun. Oct. 5, Westwood, NJ
Sunday at 10:00 AM
Hillsdale Manor · Veterans Memorial Park
Sales end soon
Harvest Fest Craft Fair & Antique Corner, Sun. Oct. 5, Westwood, NJ
Sunday at 10:00 AM
Hillsdale Manor · Veterans Memorial Park
Sales end soon
Autumn Vibes Craft Fair
Saturday at 11:00 AM
Rhode Island · DiFazio Farm & Vineyard
Sales end soon
Autumn Vibes Craft Fair
Saturday at 11:00 AM
Rhode Island · DiFazio Farm & Vineyard
Oktoberfest at Demarest Duck Pond
Sat, Oct 11, 10:00 AM
Demarest · Demarest Duck Pond
Oktoberfest at Demarest Duck Pond
Sat, Oct 11, 10:00 AM
Demarest · Demarest Duck Pond
Pumpkin Palooza
Thu, Oct 23, 5:30 PM
Commack North · 284 Indian Head Rd
Pumpkin Palooza
Thu, Oct 23, 5:30 PM
Commack North · 284 Indian Head Rd

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Popular events

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Trends in Great Barrington

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Frequently asked questions about Great Barrington

What are the best festival events to attend?

According to Eventbrite, the best festival events are:

Halloween Wicked Walk at Weis!

Spooky Woods

Harvest Celebration and Passport Program North Fork Long Island

Holiday Trail of Lights

Which events are currently trending in Great Barrington?

The trending searches this month in Great Barrington are:

oktoberfest in berkshires

live music

craft fairs

car show

Which festival events are coming up?

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

Holdridge's Hometown Fall Festival

Hallock Homestead Annual Harvest Fest

Autumn Vibes Craft Fair

Harvest Fest Craft Fair & Antique Corner, Sun. Oct. 5, Westwood, NJ

Halloween Wicked Walk at Weis!

Halloween Wicked Walk at Weis!

Spooky Woods

Spooky Woods

Harvest Celebration and Passport Program North Fork Long Island

Harvest Celebration and Passport Program North Fork Long Island

Holiday Trail of Lights

Holiday Trail of Lights

Creepy Crawly Animals and the Spirit of Halloween

Creepy Crawly Animals and the Spirit of Halloween

Pop-up at Green Meadow Fall Fair

Pop-up at Green Meadow Fall Fair

Fall Fair

Fall Fair

Shrewsbury Holiday Craft and Vendor Fair

Shrewsbury Holiday Craft and Vendor Fair

Holdridge's Hometown Fall Festival

Holdridge's Hometown Fall Festival

St. Joseph Regional High School Craft Fair

St. Joseph Regional High School Craft Fair

Tice's Corner Fall Harvest Festival 2025

Tice's Corner Fall Harvest Festival 2025

Greater Ramsey Unico Italian Christmas Craft Fair

Greater Ramsey Unico Italian Christmas Craft Fair

Hallock Homestead Annual Harvest Fest

Hallock Homestead Annual Harvest Fest

Pumpkin Palooza at TLE Tuckahoe

Pumpkin Palooza at TLE Tuckahoe

Harvest Fest Craft Fair & Antique Corner, Sun. Oct. 5, Westwood, NJ

Harvest Fest Craft Fair & Antique Corner, Sun. Oct. 5, Westwood, NJ

Autumn Vibes Craft Fair

Autumn Vibes Craft Fair

Oktoberfest at Demarest Duck Pond

Oktoberfest at Demarest Duck Pond

Pumpkin Palooza

Pumpkin Palooza

Popular events

Things to do around Great Barrington

Trends in Great Barrington

1. Oktoberfest in berkshires

2. Live music

3. Craft fairs

4. Car show

5. Halloween

6. Christmas

7. Autumn

8. Great barrington harvest fest

9. Berkshires

10. Vfw

11. Open mic

12. Trivia