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Lenox, 6 to 8 pm
The adult only event costs $30 and is limited to 25 participants. To reserve a spot call or email: 413-637-5530 communitycenter@townoflenox.com.
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Lee, 10 a.m. - 4 p.m.
Holiday Craft Fair. December 6th 2024. 10a-4p. The Landing at Laurel Lake 600 Laurel Street Lee, MA 01238. Over 15 talented local vendors
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HOLIDAY SHOP HOP DOWNTOWN LEE
Lee, 3:00-8:00 pm
Sip and stroll through downtown Lee. Tree lighting at 6:00 in the park. Local businesses extending hours with refreshments. Restaurants offering thematic specials.
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WINTERLAND KICK OFF
Lenox, 4:00pm-6:00pm
Holiday Tree Walk, pick up your downtown map at the Lenox Chamber of Commerce.
Sales and Treats from participating downtown shops
Tree Lighting in Lilac Park
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DOWNTOWN PITTSFIELD FESTIVE FROLIC
Pittsfield, 5 - 8 p.m.
Downtown Pittsfield Festive Frolic: Friday, December 6 and Saturday, December 7
Friday, December 6:
6PM: City of Pittsfield’s Park Square Tree Lighting Ceremony
5-7PM: Hot Chocolate and Photo Ops with the Grinch at Otto’s Kitchen & Comfort
5-7PM: Wreath Art Auction to benefit the South Community Food Pantry at the Lichtenstein Center for the Arts
5:30-8PM: Free admission to the Berkshire Museum’s Festival of Trees: Aquatica
5-8PM: Free Photo Frame Decorating at Witch Slapped
See full details at https://downtownpittsfield.com/2024/11/festive-frolic-in-downtown-pittsfield-dec-6-7
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Vermont, 10 a.m. - 2 p.m.
Join United Counseling Service (UCS)’ Developmental Services division on December 7 as our Community Supports program hosts a Holiday Craft Table at the Bennington Community Market. The table will feature a variety of items, including crafts that clients crafted with support and other items created independently by clients of the Community Supports program. Stop by to see the wonderful things that our clients create and shop for one-of-a-kind gifts this holiday season! All sales benefit the Community Supports program at UCS and our clients. Please contact CBurke@ucsvt.org for more information.
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DELIGHTFUL & DELECTABLE HOLIDAY MARKET
Great Barrington, 10 a.m. - 4 p.m.
Great Barrington Arts Market (GBAM) annual Delightful and Delectable Holiday Market, a unique holiday sale featuring the best of the Berkshires handmade gifts and delicious giftable treats returns to the beautifully restored Saint James Place on Main Street in Great Barrington, MA. Get ready for a stunning lineup of local artists and makers as well as light fare in a beautiful and festive environment. With over 25 makers, Delightful and Delectable offers market goers a chance to shop a variety of gifts and support the local artist community at the same time.
For more information write to gbartsmarket@gmail.com or find us on Facebook and Instagram at GB Arts Market.
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DELIGHTFUL & DELECTABLE HOLIDAY MARKET
Windsor | Great Barrington, 10 am
Great Barrington Arts Market (GBAM) annual Delightful and Delectable Holiday Market, a unique holiday sale featuring the best of the Berkshires handmade gifts and delicious giftable treats returns to the beautifully restored Saint James Place on Main Street in Great Barrington, MA. Get ready for a stunning lineup of local artists and makers as well as light fare in a beautiful and festive environment. With over 25 makers, Delightful and Delectable offers market goers a chance to shop a variety of gifts and support the local artist community at the same time.
GBAM’s mission is to provide revenue for Berkshire and regional based artists and offer locally made products to consumers in a holiday market venue.
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HOLIDAY MARKET
Great Barrington, 10am-4pm
Delightful & Delectable Holiday Market, best of the berkshires's handmade gifts and delicious giftable treats. St. James Place.
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SHOP, SIP, SAVOR
Lenox, 12pm-5pm
Complimentary cocktails and gourmet bites, special gift at every stop
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NO. BERKSHIRE HABITAT FOR HUMANITY HOLIDAY SHOWCASE
Williamstown, 1:00pm-5:00pm
At the First Congregational Church. Showcasing mini trees made by various companies and people in the community to be raffled off to benefit the orthern Berkshire Habitat for Humanity.
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DOWNTOWN PITTSFIELD FESTIVE FROLIC
Pittsfield, 5 - 8 p.m.
Downtown Pittsfield Festive Frolic: Friday, December 6 and Saturday, December 7
Saturday, December 7:
12-3PM: European Holiday Market on Dunham Mall
12-3PM: Free Photo Ops with Santa on Dunham Mall
12-2:30PM: Free Kids’ Paint & Sip at St. Stephen’s Church
11AM-5PM: Berkshire Holiday Bazaar at Holiday Inn & Suites
1-5PM: Tinsel and Bling Holiday Art Opening with the Clock Tower Artists
12-3PM: Free Drop-In Art Making at Berkshire Art Center
12-3PM: Free Create Your Own Star Ornaments at Peace Train Tees
11:30AM-2:30PM: Free Build Your Own Cotton Ball Snowman at Marie’s North Street Eatery and Gallery
12-3PM: Free Holiday Card Making Drop-in at the Berkshire Athenaeum
12-3PM: Free Festive Bookmark Making Drop-in for Adults at the Berkshire Athenaeum
10AM-2PM: Oral History Event at the Berkshire Athenaeum
12-3PM: Free Holiday Pot Decorating at The Plant Connector; Kids’ mini winter-themed terrariums for $12.
1-2PM: Free Class: Balloon Twist for Beginners at Nene’s Deco
12-3PM: Free Photo Frame Decorating at Witch Slapped
See full details at https://downtownpittsfield.com/2024/11/festive-frolic-in-downtown-pittsfield-dec-6-7
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35TH ANNUAL STOCKBRIDGE MAIN ST AT CHRISTMAS HOLIDAY CONCERT AND GROUP SING-ALONG
Stockbridge, 5:00 pm
Join us for the 35th Annual Stockbridge Main Street at Christmas Holiday Concert and Group Sing-Along featuring The Berkshire Bach Players at the First Congregational Church Stockbridge.
A Baroque lite program, including a Christmas Concerto. Some of the most beautiful and enduring pieces of all time by Bach and Handel. A bit of violin pyrotechnics from a composer inspired by his Baroque models. AND a rousing sing-along, including Hallelujah! from Handel's oratorio Messiah.
Tickets are $40 per person. Tickets here: https://stockbridgechamber.org/visit/stockbridge-main-street-at-christmas/
Program benefits the Stockbridge Chamber of Commerce.
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DALTON TREE LIGHTING
Dalton, 5:00pm
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BREAKFAST WITH SANTA
Lenox, 9 a.m. - 10:30 a.m.
Breakfast With Santa at the United Methodist Church of Lenox on December 7th from 9:00am-10:30am. Join us for a morning with breakfast, crafts, picture opportunities, and Santa arriving on a fire truck with his friends. This is a free event (dentations welcomed). Come join the fun!
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ST. MARY'S CHRISTMAS BAZAAR
Cheshire, 9 a.m. - 3 p.m.
White Elephant Tag Sale
Christmas Crafts & Gifts
Santa's Cafe - Polish, Italian, American, & More!
Baked Goods & Candy
Jewelry
Religious Goods
Adult & Children's Chance Auctions
Money Raffle
Scratch Ticket Raffle
Large Item Raffles - Cord of Wood, Generator, & More!
50/50 to benefit the Cheshire Food Pantry!
Join us for a live auction featuring local gift certificates, items, a pallet of pellets, 100 gallons of fuel oil, & more! This auction is fun and an easy way to start if you have never been to an auction before!
Food will be available along with leftover White Elephant tag sale items from the day before!
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OUTDOOR EUROPEAN HOLIDAY MARKET
Pittsfield, Noon to 3 p.m.
Downtown Pittsfield, Inc. will host a European Holiday Market outside on Dunham Mall (100 North Street) from 12 to 3 pm on Saturday, December 7. Vendors include Baked Pastries & More, Birdseye Woodcrafts, Holmes Candle Co., Maria Ortiz, MasonAiry Craft Co., Mountain Girl Farm, Inc, St. Eithne Rd., and xtwii. Shop baked goods, handmade earrings and winter hats, hand-crafted goat milk soap, small batch candles, fine custom wood cutting boards, crystals and original artwork, and pre-Columbian art and jewelry.
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Great Barrington, 10am-12pm
Crissey Farm and Drag Story Hour Berkshires are thrilled to announce the 2nd Annual Cookies & Cocoa with the Clauses event, in partnership with Cakes in the Wild, and The Bookloft. This fun, family-friendly event will take place on Sunday, December 8, 2024, with two sessions at 10:00 AM and 12:30 PM at Crissey Farm in Great Barrington, MA.
This year’s event will bring holiday magic to the Berkshires with:
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Santa and Mrs. Claus – Presented by Drag Story Hour, families can meet the Clauses, take photos, and enjoy holiday cheer.
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Cookie Decorating – Cakes in the Wild will provide delicious, freshly baked cookies for kids to decorate.
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Hot Cocoa – Warm up with a cozy cup of cocoa, provided by Barrington Brewery.
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Storytime – Enjoy classic holiday stories read aloud, spreading the joy of the season.
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Book Giveaway – Each child will receive a gently used holiday book to take home and continue the tradition of holiday reading.
Additionally, The Bookloft will have a special table with books, crafts, and holiday items available for purchase, and every child attending the event will receive a coupon to spend at their store. This is a great way to support a local bookstore while nurturing children’s love for reading!
“Cookies & Cocoa with the Clauses is about bringing families together to celebrate the season in a joyful and inclusive environment,” said Poppy DaBubbly, Chapter Director of Drag Story Hour Berkshires. “We’re excited to collaborate with amazing local businesses to make this year’s event even more special.”
Cost: $20 kids, $5 adults. Tickets available at www.crisseyfarm.com
426 Stockbridge Rd, Great Barrington
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HOLIDAY MARKET
Great Barrington, 10am-3pm
Delightful & Delectable Holiday Market, best of the berkshires's handmade gifts and delicious giftable treats. St. James Place.
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WEST STOCKBRIDGE TREE LIGHTING
W. Stockbridge, 4:30pm-6:00pm
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ST. MARY'S LIVE AUCTION
Cheshire, Noon
White Elephant Tag Sale
Christmas Crafts & Gifts
Santa's Cafe - Polish, Italian, American, & More!
Baked Goods & Candy
Jewelry
Religious Goods
Adult & Children's Chance Auctions
Money Raffle
Scratch Ticket Raffle
Large Item Raffles - Cord of Wood, Generator, & More!
50/50 to benefit the Cheshire Food Pantry!
Join us for a live auction featuring local gift certificates, items, a pallet of pellets, 100 gallons of fuel oil, & more! This auction is fun and an easy way to start if you have never been to an auction before!
Food will be available along with leftover White Elephant tag sale items from the day before!
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Lenox, 10am-2pm
Donuts with Santa at The Belvedere (10am-12pm), Home for the Holidays Treat Tour, Outdoor Holiday Artisan Craft Market. Doctor Sax house: Winter Igloos, Gingerbread Decorating, Ice Skating.
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HOLIDAY SHOP, SIP & STROLL
Great Barrington, 2:00pm-8:00pm
The Southern Berkshire Chamber's annual Holiday Shop, Sip & Stroll returns to downtown Great Barrington on December 14!
The Stroll features dozens of fun, FREE activities for the whole family. Save the date and check out our schedule of activities here.
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Monterey, 10:00am-2:00pm
Shop gifts, baked goods and creative wares made by our therapeutic community. 54 Gould Rd.
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TRINITY CHURCH CHRISTMAS CAROLS ON THE LABYRINTH
Lenox, 3:00-4:00pm
Celebrate the spirit of Christmas with songs of the season. All community members welcome! 88 Walker St, Lenox.
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