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This holiday, we’ve got just the thing. 🎄

Santa events in Pittsfield, MA

Guided Tours at Paine Castle Troy - Victorian Stroll Dec 8th, 11-4
Sun, Dec 8, 11:00 AM
Paine Castle Troy
Guided Tours at Paine Castle Troy - Victorian Stroll Dec 8th, 11-4
Sun, Dec 8, 11:00 AM
Paine Castle Troy
Santa's Worshop for Kids, Meet and Greet
Sun, Dec 15, 11:00 AM
D'n'A Art and Event Studio
Santa's Worshop for Kids, Meet and Greet
Sun, Dec 15, 11:00 AM
D'n'A Art and Event Studio
Cookies And Milk With Santa & Mrs. Claus
Sat, Dec 7, 12:00 PM + 1 more
Pete's Sweets
Cookies And Milk With Santa & Mrs. Claus
Sat, Dec 7, 12:00 PM + 1 more
Pete's Sweets
Ugly Sweater Santa Con
Thu, Dec 12, 5:30 PM
Wahlburgers
Ugly Sweater Santa Con
Thu, Dec 12, 5:30 PM
Wahlburgers
Going fast
Santa's Workshop: Breakfast and Vendor Fair
Sun, Dec 8, 9:30 AM
German Club
Going fast
Santa's Workshop: Breakfast and Vendor Fair
Sun, Dec 8, 9:30 AM
German Club
Christmas at the Inn: A Vintage Prix Fixe Dining Experience
Sat, Dec 14, 7:00 PM
The Goldenrod Country Inn
Christmas at the Inn: A Vintage Prix Fixe Dining Experience
Sat, Dec 14, 7:00 PM
The Goldenrod Country Inn
Christinkdlemarkt at Stable Gate Farm and Winery
Sat, Dec 7, 11:00 AM + 3 more
Stable Gate Farm and Winery
Christinkdlemarkt at Stable Gate Farm and Winery
Sat, Dec 7, 11:00 AM + 3 more
Stable Gate Farm and Winery
SANTA PAINTING WORKSHOP
Sun, Dec 15, 4:00 PM
Ole Savannah Southern Table and Bar
SANTA PAINTING WORKSHOP
Sun, Dec 15, 4:00 PM
Ole Savannah Southern Table and Bar
Sales end soon
Santa Cookies & Cocoa Experience
Friday at 8:30 AM + 20 more
Bob's Trees
Sales end soon
Santa Cookies & Cocoa Experience
Friday at 8:30 AM + 20 more
Bob's Trees
3rd Annual Our Day Gala
Sat, Dec 7, 7:00 PM
Crowne Plaza Albany - the Desmond Hotel, an IHG Hotel
3rd Annual Our Day Gala
Sat, Dec 7, 7:00 PM
Crowne Plaza Albany - the Desmond Hotel, an IHG Hotel
Santa is Coming to Town!
Sat, Dec 7, 10:30 AM
Congregational Church of Burlington
Santa is Coming to Town!
Sat, Dec 7, 10:30 AM
Congregational Church of Burlington
Going fast
Bethlehem Police Departments 5th Annual Holiday Lights in the Park
Sat, Dec 7, 5:00 PM
261 Elm Ave
Going fast
Bethlehem Police Departments 5th Annual Holiday Lights in the Park
Sat, Dec 7, 5:00 PM
261 Elm Ave
A Very Very Cassie and Maggie Christmas
Mon, Dec 16, 7:30 PM
The Foundry West Stockbridge
A Very Very Cassie and Maggie Christmas
Mon, Dec 16, 7:30 PM
The Foundry West Stockbridge
Going fast
A Drag Christmas
Sun, Dec 8, 11:00 AM
Seven Dining and Catering
Going fast
A Drag Christmas
Sun, Dec 8, 11:00 AM
Seven Dining and Catering
Sales end soon
Tree Decorating and Holiday Crafts on the farm...with Goats!
Saturday at 2:00 PM
Pause & Pivot Farm
Sales end soon
Tree Decorating and Holiday Crafts on the farm...with Goats!
Saturday at 2:00 PM
Pause & Pivot Farm
Holiday Cheer Sugar Cookie Class
Sun, Dec 8, 4:00 PM
The Doggy Bag
Holiday Cheer Sugar Cookie Class
Sun, Dec 8, 4:00 PM
The Doggy Bag
Cast your 2025 Spell: Daylong vision board workshop
Sat, Dec 28, 10:00 AM
Refuge Event Space
Cast your 2025 Spell: Daylong vision board workshop
Sat, Dec 28, 10:00 AM
Refuge Event Space
Hartford Santa Bar Crawl
Sat, Dec 14, 1:00 PM
The Brownstone
Hartford Santa Bar Crawl
Sat, Dec 14, 1:00 PM
The Brownstone
Almost full
Ebenezer the Musical LIVE in Troy
Sat, Dec 7, 6:00 PM + 1 more
35 Morrison Ave
Almost full
Ebenezer the Musical LIVE in Troy
Sat, Dec 7, 6:00 PM + 1 more
35 Morrison Ave
Photos with Santa December 14th
Sat, Dec 14, 12:00 PM
1042 Main St
Photos with Santa December 14th
Sat, Dec 14, 12:00 PM
1042 Main St

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