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Events and Things to do in Old Bennington, VT

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Mugwort paper
Wed, Oct 14, 5:00 PM + 1 more
Houghtonville · Plant Connector North Adams
Mugwort paper
Wed, Oct 14, 5:00 PM + 1 more
Houghtonville · Plant Connector North Adams
Cooper Foundation Fundraiser and Awards Dinner
Sat, Nov 7, 5:30 PM
Vermont · 70 Spyglass Ln
Cooper Foundation Fundraiser and Awards Dinner
Sat, Nov 7, 5:30 PM
Vermont · 70 Spyglass Ln
Sales end soon
Wacky Williamstown, MA Scavenger Hunt
Tomorrow at 11:00 AM + 837 more
White Oaks · Tunnel City Coffee
Sales end soon
Wacky Williamstown, MA Scavenger Hunt
Tomorrow at 11:00 AM + 837 more
White Oaks · Tunnel City Coffee
Farm Tour
Friday at 3:30 PM
New York · Soul Fire Farm
Farm Tour
Friday at 3:30 PM
New York · Soul Fire Farm
Sales end soon
Bennington Bash Scavenger Hunt
Tomorrow at 11:00 AM + 837 more
Bennington · The Coffee Bar
Sales end soon
Bennington Bash Scavenger Hunt
Tomorrow at 11:00 AM + 837 more
Bennington · The Coffee Bar
PAINT & SIP- CANVAS TOTE BAG
Thu, Oct 15, 6:00 PM
Hoosick Falls · UNIHOG
PAINT & SIP- CANVAS TOTE BAG
Thu, Oct 15, 6:00 PM
Hoosick Falls · UNIHOG
Almost full
Ramble Around Town: Hayride Bar Crawl 2026
Sun, Oct 11, 2:00 PM
Maple Grove · American Legion
Almost full
Ramble Around Town: Hayride Bar Crawl 2026
Sun, Oct 11, 2:00 PM
Maple Grove · American Legion
Q-MoB Queer Men's Coffee Klatch @ Steeple City Social (North Adams, MA)
Sat, Oct 10, 10:00 AM + 7 more
Houghtonville · Steeple City Social
Q-MoB Queer Men's Coffee Klatch @ Steeple City Social (North Adams, MA)
Sat, Oct 10, 10:00 AM + 7 more
Houghtonville · Steeple City Social
Comedy On Tap at Bright Ideas Brewing in North Adams, MA!
Sat, Oct 17, 7:30 PM
Houghtonville · Bright Ideas Brewing
Comedy On Tap at Bright Ideas Brewing in North Adams, MA!
Sat, Oct 17, 7:30 PM
Houghtonville · Bright Ideas Brewing
Next Stop Comedy at The Loft at The Last Chair! - West Dover, VT
Sat, Oct 17, 7:00 PM
Vermont · The Last Chair Bar & Grill
Next Stop Comedy at The Loft at The Last Chair! - West Dover, VT
Sat, Oct 17, 7:00 PM
Vermont · The Last Chair Bar & Grill
Mr Sun plays Duke Ellington's Nutcracker Suite
Sat, Dec 5, 7:00 PM
North Bennington · The Church
Mr Sun plays Duke Ellington's Nutcracker Suite
Sat, Dec 5, 7:00 PM
North Bennington · The Church
Hike and Watercolor: A Mindful Outdoor Experience
Sat, Oct 24, 10:00 AM
New York · Boehme Legacy Forest
Hike and Watercolor: A Mindful Outdoor Experience
Sat, Oct 24, 10:00 AM
New York · Boehme Legacy Forest
PAINT & SIP
Sun, Oct 25, 3:00 PM
Bennington · Kelli's Tavern
PAINT & SIP
Sun, Oct 25, 3:00 PM
Bennington · Kelli's Tavern
Selling fast
Dec 4-6 Mount Snow $299 (2 Nights + Transport) Depart QNS NYC NJ
Fri, Dec 4, 4:00 PM
Vermont · Mount Snow Resort
Selling fast
Dec 4-6 Mount Snow $299 (2 Nights + Transport) Depart QNS NYC NJ
Fri, Dec 4, 4:00 PM
Vermont · Mount Snow Resort
The Revival House: Wine Parlor + Bites
Today at 8:00 PM + 44 more
Maple Grove · 17 Commercial St
The Revival House: Wine Parlor + Bites
Today at 8:00 PM + 44 more
Maple Grove · 17 Commercial St
Round the Regions Western Mass
Tue, Nov 10, 5:00 PM
Houghtonville · Casita
Round the Regions Western Mass
Tue, Nov 10, 5:00 PM
Houghtonville · Casita
Just added
Santa Express Evening Train
Fri, Dec 11, 7:00 PM
Bourne Brook · r.k. Miles Depot Station
Just added
Santa Express Evening Train
Fri, Dec 11, 7:00 PM
Bourne Brook · r.k. Miles Depot Station
Cricket Creek Fall Farm Picnic
Sat, Oct 24, 11:00 AM + 1 more
South Williamstown · Cricket Creek Farm
Cricket Creek Fall Farm Picnic
Sat, Oct 24, 11:00 AM + 1 more
South Williamstown · Cricket Creek Farm
Santa Express 2026
Sat, Dec 12, 10:00 AM + 4 more
Bourne Brook · r.k. Miles Depot Station
Santa Express 2026
Sat, Dec 12, 10:00 AM + 4 more
Bourne Brook · r.k. Miles Depot Station
Making Connections 2026 | Annual Conference with Brightside Up
Mon, Oct 12, 7:15 AM
Troy · Hilton Garden Inn Troy
Making Connections 2026 | Annual Conference with Brightside Up
Mon, Oct 12, 7:15 AM
Troy · Hilton Garden Inn Troy

1 of 190

Things to do around Old Bennington

Things to do in Albany

Things to do in Troy

Things to do in Saratoga Springs

Things to do in Schenectady

Things to do in Keene

Things to do in Springfield

Things to do in Northampton

Things to do in Pittsfield

Things to do in Hinsdale

Things to do in Menands

Things to do in Amherst Center

Things to do in North Amherst

Trends in Old Bennington

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1. Bennington

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Frequently asked questions about Old Bennington

What are the best events to attend?

According to Eventbrite, the best events are:

Cooper Foundation Fundraiser and Awards Dinner

PAINT & SIP- CANVAS TOTE BAG

Ramble Around Town: Hayride Bar Crawl 2026

Which events are currently trending in Old Bennington?

The trending searches this month in Old Bennington are:

Which events are coming up?

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

The Revival House: Wine Parlor + Bites

Wacky Williamstown, MA Scavenger Hunt

Bennington Bash Scavenger Hunt

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