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Winter holiday events in Great Barrington, MA

Nearly full
5th Annual Toy Giveaway
Sat, Dec 13, 11:00 AM
Hartford · The 224 Ecospace
Nearly full
5th Annual Toy Giveaway
Sat, Dec 13, 11:00 AM
Hartford · The 224 Ecospace
Sip, Swirl, & Sleigh @ Cafe Tamra
Tue, Dec 9, 6:00 PM
West Springfield · 1440 Westfield St
Sip, Swirl, & Sleigh @ Cafe Tamra
Tue, Dec 9, 6:00 PM
West Springfield · 1440 Westfield St
W.H.A.T. Winter Gala
Sat, Feb 14, 6:00 PM
Hampden · 128 Wilbraham Rd
W.H.A.T. Winter Gala
Sat, Feb 14, 6:00 PM
Hampden · 128 Wilbraham Rd
Christmas Cookie Decorating at The Red Lion Inn
Wed, Dec 10, 3:00 PM
Stockbridge · The Red Lion Inn
Christmas Cookie Decorating at The Red Lion Inn
Wed, Dec 10, 3:00 PM
Stockbridge · The Red Lion Inn
Selling quickly
Flameworking Workshop - Blown Glass Ornaments at Upper Depot Brewing
Sat, Dec 6, 1:00 PM
Hudson · Upper Depot Brewing Co.
Selling quickly
Flameworking Workshop - Blown Glass Ornaments at Upper Depot Brewing
Sat, Dec 6, 1:00 PM
Hudson · Upper Depot Brewing Co.
Nearly full
Wreath + Sip at Cooper's Daughter Spirits (Dec 5th)
Fri, Dec 5, 4:00 PM
Claverack · Cooper's Daughter Spirits at Olde York Farm
Nearly full
Wreath + Sip at Cooper's Daughter Spirits (Dec 5th)
Fri, Dec 5, 4:00 PM
Claverack · Cooper's Daughter Spirits at Olde York Farm
Ornament Decorating at The Red Lion Inn
Wed, Dec 3, 3:00 PM + 1 more
Stockbridge · The Red Lion Inn
Ornament Decorating at The Red Lion Inn
Wed, Dec 3, 3:00 PM + 1 more
Stockbridge · The Red Lion Inn
Wreath + Sip at Cooper's Daughter Spirits (Dec 12th)
Fri, Dec 12, 4:00 PM
Claverack · Cooper's Daughter Spirits at Olde York Farm
Wreath + Sip at Cooper's Daughter Spirits (Dec 12th)
Fri, Dec 12, 4:00 PM
Claverack · Cooper's Daughter Spirits at Olde York Farm
WINTER BALL
Sat, Dec 27, 9:00 PM
Hartford · Tropix Caribbean Grille
WINTER BALL
Sat, Dec 27, 9:00 PM
Hartford · Tropix Caribbean Grille
7th Annual Yule Oddities and Curiosities Night Market
Fri, Dec 12, 6:00 PM
Poughkeepsie · Locust Grove Estate
7th Annual Yule Oddities and Curiosities Night Market
Fri, Dec 12, 6:00 PM
Poughkeepsie · Locust Grove Estate
Family Friendly Movie Night at White Lion: How The Grinch Stole Christmas
Fri, Dec 5, 6:00 PM
Springfield · White Lion Brewing Company
Family Friendly Movie Night at White Lion: How The Grinch Stole Christmas
Fri, Dec 5, 6:00 PM
Springfield · White Lion Brewing Company
Pajama Brunch at The Red Lion Inn
Sun, Dec 28, 8:30 AM
Stockbridge · The Red Lion Inn
Pajama Brunch at The Red Lion Inn
Sun, Dec 28, 8:30 AM
Stockbridge · The Red Lion Inn
Holiday Ceramic Pottery Paint & Sip
Sat, Dec 13, 4:00 PM
Troy · The Whistling Kettle
Holiday Ceramic Pottery Paint & Sip
Sat, Dec 13, 4:00 PM
Troy · The Whistling Kettle
Sales end soon
MCC Holiday Business Card Exchange 2025
Monday at 5:30 PM
West Hartford · The Pond House
Sales end soon
MCC Holiday Business Card Exchange 2025
Monday at 5:30 PM
West Hartford · The Pond House
Holiday Daytime Tour of the Hotchkiss-Fyler House Museum
Sun, Dec 7, 1:00 PM + 26 more
Torrington · Torrington Historical Society
Holiday Daytime Tour of the Hotchkiss-Fyler House Museum
Sun, Dec 7, 1:00 PM + 26 more
Torrington · Torrington Historical Society
Nearly full
Stained Glass Holiday Ornament Workshop - December Class
Sat, Dec 6, 10:00 AM
Albany · Shaker Heritage Society
Nearly full
Stained Glass Holiday Ornament Workshop - December Class
Sat, Dec 6, 10:00 AM
Albany · Shaker Heritage Society
Selling quickly
A Winter Solstice Eve
Sun, Dec 21, 3:00 PM
Wallkill · Magnanini Winery, Restaurant, Distillery & Wedding Venue
Selling quickly
A Winter Solstice Eve
Sun, Dec 21, 3:00 PM
Wallkill · Magnanini Winery, Restaurant, Distillery & Wedding Venue
Alec Mapa: "The Buttcracker"
Sun, Dec 7, 7:30 PM
West Stockbridge · The Foundry West Stockbridge
Alec Mapa: "The Buttcracker"
Sun, Dec 7, 7:30 PM
West Stockbridge · The Foundry West Stockbridge
Selling quickly
Prime Rib Holiday Beer Dinner
Wed, Dec 10, 6:00 PM
Westfield · Tin Bridge Brewing Co.
Selling quickly
Prime Rib Holiday Beer Dinner
Wed, Dec 10, 6:00 PM
Westfield · Tin Bridge Brewing Co.
Holiday Candlelight Tours of the Historic Hotchkiss-Fyler House Museum
Wed, Dec 10, 5:00 PM + 5 more
Torrington · Torrington Historical Society
Holiday Candlelight Tours of the Historic Hotchkiss-Fyler House Museum
Wed, Dec 10, 5:00 PM + 5 more
Torrington · Torrington Historical Society

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