find Halloween events for every vibe.

Dreamers hollow events in Bennington, VT

Awesome Scavenger Hunt! - Dartmouth Dash & Downtown Discoveries
Today at 8:00 AM + 99 more
Lewiston · 41 Lebanon St
Awesome Scavenger Hunt! - Dartmouth Dash & Downtown Discoveries
Today at 8:00 AM + 99 more
Lewiston · 41 Lebanon St
STRANGEHOUSE PRESENTS -The Strangehouse Vampire Cabaret & Sideshow!
Fri, Oct 24, 7:00 PM
Zena · Colony
STRANGEHOUSE PRESENTS -The Strangehouse Vampire Cabaret & Sideshow!
Fri, Oct 24, 7:00 PM
Zena · Colony
Q-MoB Apple Picking at Riiska Brook Orchard (Sandisfield, MA)
Saturday at 1:30 PM
Massachusetts · Riiska Brook Orchard
Q-MoB Apple Picking at Riiska Brook Orchard (Sandisfield, MA)
Saturday at 1:30 PM
Massachusetts · Riiska Brook Orchard
Spooktacular Boos & Brews
Sat, Oct 18, 1:00 PM
Pine Hill · Simsbury Meadows Performing Arts Center
Spooktacular Boos & Brews
Sat, Oct 18, 1:00 PM
Pine Hill · Simsbury Meadows Performing Arts Center
2026 Vision Board Party
Sun, Jan 18, 1:00 PM
· Tatnuck Post No 288
2026 Vision Board Party
Sun, Jan 18, 1:00 PM
· Tatnuck Post No 288
A Date Night Adventure! - Dartmouth Dash & Downtown Discoveries
Today at 3:00 PM + 40 more
Lewiston · 41 Lebanon St
A Date Night Adventure! - Dartmouth Dash & Downtown Discoveries
Today at 3:00 PM + 40 more
Lewiston · 41 Lebanon St
Sales end soon
Saugerties Showdown, NY Amazing Race & Tour
Tomorrow at 11:00 AM + 137 more
Saugerties · Bluestone Coffee Roasting Company
Sales end soon
Saugerties Showdown, NY Amazing Race & Tour
Tomorrow at 11:00 AM + 137 more
Saugerties · Bluestone Coffee Roasting Company
Balebe & Northern Belle presents: Beads & Belles!
Sat, Oct 25, 6:00 PM
Breakneck · Balebe Beading Studio
Balebe & Northern Belle presents: Beads & Belles!
Sat, Oct 25, 6:00 PM
Breakneck · Balebe Beading Studio
Little Days & Bernie Barlow
Today at 7:00 PM
Zena · Colony
Little Days & Bernie Barlow
Today at 7:00 PM
Zena · Colony
Soul Alchemy Weekend Retreat
Fri, Mar 20, 3:00 PM
Halihan Hill · 460 Glenerie Blvd
Soul Alchemy Weekend Retreat
Fri, Mar 20, 3:00 PM
Halihan Hill · 460 Glenerie Blvd
Lebanon Holiday Girls Night Out!
Thu, Nov 6, 5:30 PM
Lebanon · Hilton Garden Inn Hanover Lebanon
Lebanon Holiday Girls Night Out!
Thu, Nov 6, 5:30 PM
Lebanon · Hilton Garden Inn Hanover Lebanon
Selling quickly
Moonlight Masquerade Dracula Ball
Sat, Oct 25, 8:00 PM
Newberry Corner · Torrington Elks Lodge #372
Selling quickly
Moonlight Masquerade Dracula Ball
Sat, Oct 25, 8:00 PM
Newberry Corner · Torrington Elks Lodge #372
Sales end soon
Halloween Cake Decorating Class at Canton Ben & Jerry's
Saturday at 10:00 AM
Canton Valley · Ben & Jerry's
Sales end soon
Halloween Cake Decorating Class at Canton Ben & Jerry's
Saturday at 10:00 AM
Canton Valley · Ben & Jerry's
Sales end soon
Sip & Paint-Halloween Sign Post
Saturday at 5:00 PM
Newberry Corner · Market Street Creatives
Sales end soon
Sip & Paint-Halloween Sign Post
Saturday at 5:00 PM
Newberry Corner · Market Street Creatives
Just added!
New England Ghosts - Real Spooky Stories
Mon, Oct 20, 5:30 PM
North Brookfield · 161 N Main St
Just added!
New England Ghosts - Real Spooky Stories
Mon, Oct 20, 5:30 PM
North Brookfield · 161 N Main St
Manufacturing Happy Hour: Boos & Brews!
Wed, Oct 29, 4:00 PM
Connecticut · Back East Brewery & Kitchen
Manufacturing Happy Hour: Boos & Brews!
Wed, Oct 29, 4:00 PM
Connecticut · Back East Brewery & Kitchen
Just added!
Comedy Night at Brignole Vineyards
Fri, Nov 28, 7:30 PM
Floydville · Brignole Vineyards
Just added!
Comedy Night at Brignole Vineyards
Fri, Nov 28, 7:30 PM
Floydville · Brignole Vineyards
Family-Friendly Catskills Hike: Fall Forest + Visit an Old Quarry
Sat, Oct 25, 9:30 AM
Plaat Clove · Huckleberry Point Trailhead
Family-Friendly Catskills Hike: Fall Forest + Visit an Old Quarry
Sat, Oct 25, 9:30 AM
Plaat Clove · Huckleberry Point Trailhead
Just added!
An Afternoon with Jon Lewis
Sat, Oct 18, 1:00 PM
Lebanon · Books-A-Million
Just added!
An Afternoon with Jon Lewis
Sat, Oct 18, 1:00 PM
Lebanon · Books-A-Million

Trends in Bennington

Explore more trends

Awesome Scavenger Hunt! - Dartmouth Dash & Downtown Discoveries

Awesome Scavenger Hunt! - Dartmouth Dash & Downtown Discoveries

STRANGEHOUSE PRESENTS -The Strangehouse Vampire Cabaret & Sideshow!

STRANGEHOUSE PRESENTS -The Strangehouse Vampire Cabaret & Sideshow!

Q-MoB Apple Picking at Riiska Brook Orchard (Sandisfield, MA)

Q-MoB Apple Picking at Riiska Brook Orchard (Sandisfield, MA)

Spooktacular Boos & Brews

Spooktacular Boos & Brews

2026 Vision Board Party

2026 Vision Board Party

A Date Night Adventure! - Dartmouth Dash & Downtown Discoveries

A Date Night Adventure! - Dartmouth Dash & Downtown Discoveries

Saugerties Showdown, NY Amazing Race & Tour

Saugerties Showdown, NY Amazing Race & Tour

Balebe & Northern Belle presents: Beads & Belles!

Balebe & Northern Belle presents: Beads & Belles!

Little Days & Bernie Barlow

Little Days & Bernie Barlow

Soul Alchemy Weekend Retreat

Soul Alchemy Weekend Retreat

Lebanon Holiday Girls Night Out!

Lebanon Holiday Girls Night Out!

Moonlight Masquerade Dracula Ball

Moonlight Masquerade Dracula Ball

Halloween Cake Decorating Class at Canton Ben & Jerry's

Halloween Cake Decorating Class at Canton Ben & Jerry's

Sip & Paint-Halloween Sign Post

Sip & Paint-Halloween Sign Post

New England Ghosts - Real Spooky Stories

New England Ghosts - Real Spooky Stories

Manufacturing Happy Hour: Boos & Brews!

Manufacturing Happy Hour: Boos & Brews!

Comedy Night at Brignole Vineyards

Comedy Night at Brignole Vineyards

Family-Friendly Catskills Hike: Fall Forest + Visit an Old Quarry

Family-Friendly Catskills Hike: Fall Forest + Visit an Old Quarry

An Afternoon with Jon Lewis

An Afternoon with Jon Lewis

Things to do around Bennington

Trends in Bennington

1. Halloween

2. Paint and sip

3. Craft fair

4. October

5. Car show

6. Autumn

7. Kids events

8. Monument art and cultural center

9. September

10. Singles

11. Open mic

12. Comedy