The Christmas and holiday season is one of our favorite times of year here in the Berkshires! Each year the list of amazing holiday events and activities grows. Here is your guide to the Berkshires' many December and holiday festivities!
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Hancock Holidays
1843 West Housatonic St., Pittsfield, Massachusetts 01201Visit Hancock Shaker Village for a magical winter weekend, filled with wagon rides, holiday crafting, Shaker baking in the Brick Dwelling, brunch with Santa, a gingerbread house contest, carols, and candlelit strolls throughout the beautifully decorated village.
Dates: December 6th to December 8th: 10am – 4pm.
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Stockbridge Main Street at Christmas
Main Street, Stockbridge, MassachusettsThe town of Stockbridge, made famous by Norman Rockwell’s painting of the village during the holidays, becomes a magical New England setting decorated with holiday wreaths and festive lights, as the town celebrates Stockbridge Main Street at Christmas December 6, 7 & 8, 2019. The holiday celebration offers a full range of activities, with highlights including holiday readings, house tours, caroling, and a holiday concert.
Dates: December 6th - 8th:
Hours: December 6th: 5pm - 6:30pm | Saturday December 7th: 11am - 7pm | Sunday December 8th: 12pm - 2pm
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Handmade Holiday Shindy
40 Mellville St., Pittsfield, Massachusetts 01201Known as one of the most spectacular handmade craft fairs in the region; the Holiday Shindy has boasted all sorts of artisans in the past, including woodworkers, toymakers, printers, jewelers, ceramicists, apothecaries, clothing designers, upcyclers, farmers and more!
There will be food and music. Admission is $3 for the general public. Children under the age of 12 are free.
Dates: December 14th &15th: 10am - 5pm
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Botanical Garden Holiday Marketplace
5 W Stockbridge Rd, Stockbridge, Massachusetts 01262This annual year-end event finds the Garden transformed into a glistening holiday market featuring the Gallery of Wreaths, a Garden tradition offering one-of-a-kind wreaths created by some of the area’s most talented designers and artists. A holiday plant sale features hand-selected flowering plants, traditional centerpieces and holiday swags, and regional craft vendors offer a range of products from hand-made giftware and jewelry to beeswax and felted products.
Dates: Saturday December 7th & Sunday December 8th 10am - 4pm
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Handmade Holiday Fest
63 Flansburg Ave, Dalton, Massachusetts 01226Now a Berkshire winter tradition, the Handmade Holiday Festival is a curated marketplace that fills the historic Stationery Factory with over 60 artisans, farmers, and food producers. From pottery and jewelry to gourmet food items and body care products, the Handmade Holiday Festival is a one-stop holiday shopping destination. The Festival also serves as a testing ground for new artisans and a cornerstone sale for seasoned vendors. It’s a way to support local entrepreneurs, find unique gifts, and keep holiday spending in the community.
Entrance fee: $2 (kids under 13 are free)**All proceeds support Roots Rising's mission to empower youth and build community through food and farming.**
Dates: Saturday December 7th 10am - 5pm & Sunday December 8th 10am - 3pm
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FESTIVE Holiday Market
508 State Road, North Adams, Massachusetts 01247100 Makers, 25 Performers, 2 Chefs and…YOU
Immerse in beautiful and delicious handcrafted gifts at Greylock WORKS’ 2nd annual Fall FESTIVE – a holiday market celebrating the unique magic of the Berkshires and beyond.
Set in an expansive, light-filled mill, the 30,000 square foot open marketplace will include culinary crafters, local farmers, fermenters, and the region’s best artisan makers
Date: Saturday November 23rd 10am-4pm
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Winterlights at Naumkeag
5 Prospect Hill Rd, Stockbridge, Massachusetts 01262Trustees' Winterlights returns and is bigger and better than ever. Come for a magical experience at the beautiful garden property in Stockbridge, sparkle with thousands of shimmering and artfully designed holiday lights. Bring the family for scavenger hunts, crafts, seasonal characters and experiences, food and refreshments, and more.
Pricing: Members: $12 | Nonmembers: $17 | Under 12: FREE
Dates:Thursday November 21st to Tuesday December 31st 5pm - 8pm
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Holiday House tours at The Mount
2 Plunkett St, Lenox, Massachusetts 01240Start a new tradition this holiday season! Edith Wharton’s Berkshire home is adorned with festive decorations provided by the Lenox Garden Club.
The Lenox Garden Club will once again be filling The Mount with festive cheer, visit The Mount to see this year’s decorations- on display throughout the house.
Special events include: Winter Storytime with Grace Lin: Saturday, November 30, 2:00 PM || Paper Ornament Making: Saturday, December 7, 12:00 PM – 4:00 PM || Holiday Concert with Samantha Talora & Ron Ramsay: Saturday, December, 21, 2:00 PM
House Tour Dates: Saturdays & Sundays 11am – 4pm Now through February 2019
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Festival of Trees at the Berkshire Museum
39 South Street, City of Pittsfield, MassachusettsInvite your friends and family to join you as you discover more than 100 dazzling, decorated trees in Festival of Trees 2019: Heroes! This year’s Festival of Trees includes a weekly hands-on gallery program, musical performances, and more.
Dates: Saturday November 23rd to Saturday January 4th. 5pm - 7pm
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Holiday Tours at Ventfort Hall
104 Walker St, Lenox, Massachusetts 01240Tour the beautiful Gilded Age mansion all decorated for the holidays. The house will be decorated from late November through early January.
Dates: Guided tours scheduled every hour on the hour. Monday - Friday 11am - 4pm || Saturday 10am - 4pm || Sunday 10am - 3pm
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Holiday Shop, Sip & Stroll
Railroad St, Great Barrington, MassachusettsHead to downtown Great Barrington on Saturday December 8th for a full day of fun for Kids and Adults alike.
Date: December 14, 2019 3pm – 8:30pm
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Holiday Train Rides
3 Hoosac St, Adams, Massachusetts 01220Two wonderful holiday train rides for all ages!
1) Tinseliner Trains with Santa Claus - Enjoy a 1950's Christmas train ride with a visit from Santa. Trip includes a layover at the PopCares Tree Lot to pick a tree for pick up later. Also, enjoy hot cocoa and roasted marshmallows.
Dates: Nov 29-30, Dec 1, 7-8, 14-15 & 21-22. Departures times vary per day; check for tickets for more details.
2) Mistletoe & Martini... and Music Trains - Enjoy a holiday version of our cabaret train with live holiday music by Sam and Ron, and BYO beverages and snacks.
Dates: Saturdays, Nov 30 & Dec 14th with a 6:30 pm departure.
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A Christmas Carol
111 South Street, Pittsfield, Massachusetts 01201Celebrate the timeless holiday tradition of A Christmas Carol with the whole family, and revel in the joy and redemptive power of Christmas as told in the timeless tale of Ebenezer Scrooge, the infamous miser who is shown the error of his ways and reformed by four spirits. Journey back to Victorian England and experience the classic story filled with holiday carols and the wonderment of the season. At The Colonial Theatre | Tickets: Adult: $39 • Child: $29;
Dates: December 7th (sensory friendly event also on December 21st)
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The Nutcracker Ballet
111 South Street, Pittsfield, Massachusetts 01201Albany Berkshire Ballet's The Nutcracker,
See Event Details Here
Albany Berkshire Ballet (ABB) will present its 45th annual tour of The Nutcracker in 4 cities across the Northeast Nov 30-Dec 21, 2019. A beloved holiday tradition, ABB's Nutcracker features magnificent principal dancers from around the country accompanied by 150-200 local area students per city in its youth casts.
About the Nutcracker:
The Nutcracker tells the story of a young girl, Clara, and the magical dream she has one Christmas Eve. Set to Tchaikovsky’s timeless music, the story of The Nutcracker follows the adventures of Clara and her Nutcracker Prince as they conquer the Mouse King and embark on a magical journey to The Land of Sweets. Choreographed by Madeline Cantarella Culpo and featuring sets by Carl Sprague and costumes by Rita Watson & Victile Donahue, The Nutcracker is sure to delight all ages
Dates: December 7th & 8th: Hours: December 7th: 2:30 and 6:30 || December 8th: 1:30 and 4:30
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