Discover September Events & Activities in Bennington, VT

Max Gomez & Shannon McNally at The Coffee Bar
Sun, Sep 14, 6:30 PM
The Coffee Bar
Max Gomez & Shannon McNally at The Coffee Bar
Sun, Sep 14, 6:30 PM
The Coffee Bar
Mt. Anthony Union High School Class of 2000, 25-Year Reunion
Sat, Sep 13, 6:00 PM
Bennington Elks Lodge #567
Mt. Anthony Union High School Class of 2000, 25-Year Reunion
Sat, Sep 13, 6:00 PM
Bennington Elks Lodge #567
Awesome Scavenger Hunt! - The Revolutionary Ways of Bennington
Mon, Sep 1, 8:00 AM + 29 more
Monument Square
Awesome Scavenger Hunt! - The Revolutionary Ways of Bennington
Mon, Sep 1, 8:00 AM + 29 more
Monument Square
VCDA 2025 Fall Conference
Wed, Sep 24, 9:00 AM
Old School Enrichment Center
VCDA 2025 Fall Conference
Wed, Sep 24, 9:00 AM
Old School Enrichment Center
Comedy On Tap at Bright Ideas Brewing in North Adams, MA!
Sat, Sep 13, 7:30 PM
Bright Ideas Brewing
Comedy On Tap at Bright Ideas Brewing in North Adams, MA!
Sat, Sep 13, 7:30 PM
Bright Ideas Brewing
Project Management Techniques Certification in North Adams, MA
Fri, Sep 26, 9:00 AM + 1 more
Regus
Project Management Techniques Certification in North Adams, MA
Fri, Sep 26, 9:00 AM + 1 more
Regus
Live Comedy at Bounti-Fare Restaurant in Adams, MA!
Fri, Sep 12, 8:00 PM
Bounti-Fare Restaurant & Catering
Live Comedy at Bounti-Fare Restaurant in Adams, MA!
Fri, Sep 12, 8:00 PM
Bounti-Fare Restaurant & Catering
Eastbound Throwdown '25
Fri, Sep 5, 12:00 PM
The Irwin Farm
Eastbound Throwdown '25
Fri, Sep 5, 12:00 PM
The Irwin Farm
PRACTICAL CARBINE - Cropseyville, NY
Fri, Sep 26, 9:00 AM
Brunswick Sportsmans Club
PRACTICAL CARBINE - Cropseyville, NY
Fri, Sep 26, 9:00 AM
Brunswick Sportsmans Club
Bennington Bash Scavenger Hunt
Mon, Sep 1, 11:00 AM + 59 more
The Coffee Bar
Bennington Bash Scavenger Hunt
Mon, Sep 1, 11:00 AM + 59 more
The Coffee Bar
Bennington Bash Amazing Race & Tour
Mon, Sep 1, 11:00 AM + 59 more
The Coffee Bar
Bennington Bash Amazing Race & Tour
Mon, Sep 1, 11:00 AM + 59 more
The Coffee Bar
Adventurous Scavenger Hunt! - Williamstown Whimsical Wanderers
Mon, Sep 1, 8:00 AM + 29 more
Field Park
Adventurous Scavenger Hunt! - Williamstown Whimsical Wanderers
Mon, Sep 1, 8:00 AM + 29 more
Field Park
Wacky Williamstown, MA Amazing Race & Tour
Mon, Sep 1, 11:00 AM + 59 more
Tunnel City Coffee
Wacky Williamstown, MA Amazing Race & Tour
Mon, Sep 1, 11:00 AM + 59 more
Tunnel City Coffee
Wacky Williamstown, MA Scavenger Hunt
Mon, Sep 1, 11:00 AM + 59 more
Tunnel City Coffee
Wacky Williamstown, MA Scavenger Hunt
Mon, Sep 1, 11:00 AM + 59 more
Tunnel City Coffee
PMP Live Instructor Led Certification Training Bootcamp North Adams, MA
Sat, Sep 20, 9:00 AM + 1 more
North Adams
PMP Live Instructor Led Certification Training Bootcamp North Adams, MA
Sat, Sep 20, 9:00 AM + 1 more
North Adams
Meet & Greet Celebrity Chef Mary Ann Esposito from TV's Ciao Italia
Sat, Sep 6, 12:00 PM
The Italian Market of Manchester
Meet & Greet Celebrity Chef Mary Ann Esposito from TV's Ciao Italia
Sat, Sep 6, 12:00 PM
The Italian Market of Manchester
Charcuterie Board & Sip
Sun, Sep 14, 3:00 PM
Wallie's of Greenwich
Charcuterie Board & Sip
Sun, Sep 14, 3:00 PM
Wallie's of Greenwich
Cj & Marcus’ Wedding Shower
Sun, Sep 7, 1:00 PM
150 Meadowview Dr
Cj & Marcus’ Wedding Shower
Sun, Sep 7, 1:00 PM
150 Meadowview Dr
Basics of High Performance Building
Tue, Sep 9, 3:30 PM
Veterans of Foreign Wars
Basics of High Performance Building
Tue, Sep 9, 3:30 PM
Veterans of Foreign Wars

Max Gomez & Shannon McNally at The Coffee Bar

Max Gomez & Shannon McNally at The Coffee Bar

Mt. Anthony Union High School Class of 2000, 25-Year Reunion

Mt. Anthony Union High School Class of 2000, 25-Year Reunion

Awesome Scavenger Hunt! - The Revolutionary Ways of Bennington

Awesome Scavenger Hunt! - The Revolutionary Ways of Bennington

VCDA 2025 Fall Conference

VCDA 2025 Fall Conference

Comedy On Tap at Bright Ideas Brewing in North Adams, MA!

Comedy On Tap at Bright Ideas Brewing in North Adams, MA!

Project Management Techniques Certification in North Adams, MA

Project Management Techniques Certification in North Adams, MA

Live Comedy at Bounti-Fare Restaurant in Adams, MA!

Live Comedy at Bounti-Fare Restaurant in Adams, MA!

Eastbound Throwdown '25

Eastbound Throwdown '25

PRACTICAL CARBINE - Cropseyville, NY

PRACTICAL CARBINE - Cropseyville, NY

Bennington Bash Scavenger Hunt

Bennington Bash Scavenger Hunt

Bennington Bash Amazing Race & Tour

Bennington Bash Amazing Race & Tour

Adventurous Scavenger Hunt! - Williamstown Whimsical Wanderers

Adventurous Scavenger Hunt! - Williamstown Whimsical Wanderers

Wacky Williamstown, MA Amazing Race & Tour

Wacky Williamstown, MA Amazing Race & Tour

Wacky Williamstown, MA Scavenger Hunt

Wacky Williamstown, MA Scavenger Hunt

PMP Live Instructor Led Certification Training Bootcamp North Adams, MA

PMP Live Instructor Led Certification Training Bootcamp North Adams, MA

Meet & Greet Celebrity Chef Mary Ann Esposito from TV's Ciao Italia

Meet & Greet Celebrity Chef Mary Ann Esposito from TV's Ciao Italia

Charcuterie Board & Sip

Charcuterie Board & Sip

Cj & Marcus’ Wedding Shower

Cj & Marcus’ Wedding Shower

Basics of High Performance Building

Basics of High Performance Building

Things to do around Bennington

Trends in Bennington

1. Craft fair

2. Monument art and cultural center

3. Car show

4. Kids events

5. September

6. Hurray for the riff raff

7. Halloween

8. Pride events

9. October events

10. Drag queen bingo

11. Singles

12. Little city cider company