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Sheffield winter farmers market

Dewey Hall Holiday Cookie Sale

Sheffield, MA

Dewey Hall will hold their annual Holiday Cookie Sale at the Sheffield Winter Holiday Market — Snowballs, Shortbread, Pfeffernausse, Chocolate Chip and more.

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Holiday Shindy

Holiday Marketplace

Gilded Age Christmas

Lenox, MA

Ventfort Hall is decorated for the holidays in 19th-century style, with lighted tree and stockings by the fire and more, and open for self-guided explorations.

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Holiday Art Market at Ventfort Hall

Print room popup: Florencia en el Amazonas

Gallery tour @ the Clark

Charlie’s Trains for the holidays

Florencia en el Amazonas — Met @ the Clark

Tinseliner holiday trains

Daniel Catán’s Florencia en el Amazonas

Great Barrington, MA

Sung in Spanish and inspired by the magical realism of Gabriel García Márquez, Mexican composer Daniel Catán’s 1996 opera focuses on an opera diva who returns to Brazil to perform and to search for her lost lover.

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A Christmas Carol

Holiday shop, sip and stroll

Great Barrington, MA

Great Barrington's annual holiday downtown celebration returns with a holiday market, bonfire and s'mores, music and parades, hayrides and more — and all stroll activities are free.

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Tinseliner holiday train

Mistletoe Cabaret Train

Historic Sheffield Winter Wonderland

LumiNAMA Holiday Lights Festival

North Adams, MA

LumiNAMA Holiday Lights Festival returns to brighten and celebrate downtown North Adams during the holiday season, as storefronts are illuminated with 20 different window displays.

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Mickey’s Christmas Carol

Great Barrington, MA

Disney’s favorite mouse and friends retell Charles Dickens’ Christmas classic in this animated short from 1983. The film will play on loop during Great Barrington’s Holiday Stroll.

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Winterlights @ Naumkeag

Stockbridge, MA

Winterlights is back, filling the gardens with holiday light and sound for a magical outdoor experience at Naumkeag as it shimmers with thousands of lights.

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Nightwood @ the Mount

Lenox, MA

Music and light fill the woods at Edith Wharton's historic house with a celebration of the winter solstice and fire in the dark.

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SALA Holiday Lounge: Tipsy Carol Sing-along

West Stockbridge, MA

Stressful holiday shopping? Need a glass of vino? Can't spend another night wrapping gifts and watching reruns of Friends? The Foundry Bar and SALA Boutique will be open — tonight with holiday song.

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Tinseliner holiday trains

Adams, MA

Santa will be visiting the Berkshires again this year and will join the Hoosac Valley Line's Tinseliner train for Christmas carols and good cheer.

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Mistletoe Cabaret Train

A Christmas Carol

A Christmas Memory by Truman Capote

Vocalis Youth Choir holiday concert

Great Barrington, MA

Vocalis Youth Choir bring beautiful festive sounds of the season in a free holiday concert, beginning after the downtown Holiday Shop, Sip and Stroll fireworks.

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North Berkshire Contra Dance

Glori Wilder plays live @ the Barn

Egremont, MA

Glori Wilder, an R&B, Soul, and Pop singer-songwriter living in the woods of Connecticut, will perform at the Egremont Barn.

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Maxine Lyle’s Step Show: The Musical

North Adams, MA

Maxine Lyle’s new work Step Show: The Musical showcases African American step dance and its role in Black college life, infusing body percussion with hip-hop, R&B, and soul.

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BTW Berkshires
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