Holiday Happenings in the Berkshires

Ongoing Events

Festival of Trees at Berkshire Museum
2019 Festival of Trees: Hero’s, is a celebration of those who inspire us featuring more than 100 dazzling, decorated holiday trees. November 16 – December 5, 2020

Get Holiday Crafty at Berkshire Paint and Sip
Create a meaningful gift for someone on your gift list or just join in to socialize, sip a beverage and get in the Holiday spirit! Check website for various classes through December 22.

Winterlights at Naumkeag
Naumkeag will be illuminated with thousands of shimmering holiday lights and designed light installations with performances and activities for the whole family. Don your coats, pull on your boots and join us for a new family tradition! Weekends, November 22 – December 29. 

Stockbridge Main Street at Christmas
The 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. Enjoy a full range of activities, with highlights including holiday readings, house tours, caroling, and a holiday concert. December 6 – 8

A Christmas Carol
Celebrate the timeless holiday tradition of A Christmas Carol at the Colonial Theatre 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. December 7 – 21. Check website for specific days/times.

Holiday House Tours at The Mount
Join us as we celebrate the holidays in keeping with the customs and traditions of the Gilded Age. Festive decorations throughout the mansion provided by the Lenox Garden Club and special events throughout December. 11AM – 4PM. Weekends, November 23 – January 5.

Tinseliner Train 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. Departures at 12pm, 2:30pm, 4:30pm, & 6:30pm. Weekends, November 30 – December 22

Visit with Santa
Join us weekend mornings as Santa stops in to visit with the young and the young-at-heart customers of Ward’s Nursery, Great Barrington. Stop by and say Hello! 9AM – 12PM. November 29 – December 21

Events

December 5
Holidays Lights at Arrowhead
Join us for a candlelit tour of the house and 19th century holiday experience complete with winter past-times, refreshments and readings. 6:30PM

Wreath-N-Cork at Whitney’s Farm Market & Garden Center
Come enjoy an evening out at the farm with your friends and family! The event includes at 12″ wreath, a bow and all sorts of ornaments to make it your own. There will be festive display of wines as well as light refreshments made by our bakery and deli! Space is limited, so get your ticket before they sell out! 6PM– 8PM

December 6
Yule Jam at Hancock Shaker Village
Grab an ugly sweater, get in the holiday spirit, and join us at the Village for Yule Jam. We’ll have live music in The Believers’ Room, a roaring fire, food trucks, cool holiday cocktails, and local beer. 7PM – 9PM.

Tree Lighting at Blantyre
Ignite the holiday spirit at Blantyre! Enjoy homemade cookies, hot chocolate and apple cider. Santa will arrive for a visit with the kids! 5PM – 6PM

Downtown Festive Frolic
2nd Annual Festive Frolic in downtown Pittsfield! Enjoy free and low-cost family-friendly activities in honor of the holiday season. See website for details. The Downtown Festive Frolic is sponsored by Greylock Federal Credit Union, Phoenix Theatres Beacon Cinema, Qualprint, the City of Pittsfield, and Downtown Pittsfield, Inc. 5PM – 8PM and beyond.

North Pole Pub Crawl
Part of Downtown Pittsfield Festive Frolic! You are responsible for your own food and drinks. Creative costumes are encouraged and REWARDED! Check website for more information. The Downtown Festive Frolic is sponsored by Greylock Federal Credit Union, Phoenix Theatres Beacon Cinema, Qualprint, the City of Pittsfield, and Downtown Pittsfield, Inc. 5PM – 1AM.

Lenox Winterland
Come to downtown Lenox to enjoy some winter fun. See the beautifully decorated shops, have a hot chocolate or mulled wine, warm up by the outdoor fire, and participate in the festivity of the season.

December 7
Handmade Holiday Festival!
Now a Berkshire winter tradition, the Handmade Holiday Festival is a curated marketplace that fills the historic Stationery Factory with nearly 70 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. 10AM – 5PM

Santa at The Beacon Cinema
Santa Claus is coming to The Beacon Cinema as part of the Downtown Pittsfield Festive Frolic! Meet Santa and have your child’s picture taken with Santa and receive a 4×6 photo. In exchange, we ask that you come prepared to donate a brand new item of warm clothing to the Berkshire Community Action Council’s Warm Clothing Program. The Downtown Festive Frolic is sponsored by Greylock Federal Credit Union, Phoenix Theatres Beacon Cinema, Qualprint, the City of Pittsfield, and Downtown Pittsfield, Inc. 10AM – 1PM.

Downtown Festive Frolic
2nd Annual Festive Frolic in downtown Pittsfield! Enjoy free and low-cost family-friendly activities in honor of the holiday season. See website for details. The Downtown Festive Frolic is sponsored by Greylock Federal Credit Union, Phoenix Theatres Beacon Cinema, Qualprint, the City of Pittsfield, and Downtown Pittsfield, Inc. 10AM – 3PM.

Lenox Winterland
Come to downtown Lenox to enjoy some winter fun. See the beautifully decorated shops, have a hot chocolate or mulled wine, warm up by the outdoor fire, and participate in the festivity of the season.

Paper Ornament Making at The Mount
Gather inspiration from The Mount’s holiday decorations and then make your own holiday ornament to take home with you. Included with admission. 12PM – 4PM

Your Choice Holiday Workshop
Ward’s Nursery staff help you create your own Holiday Kissing Ball or Boxwood Tree. A fragrant craft of fresh boxwood dresses porches or tabletops through the holidays. Unique ornaments from Ward’s holiday crafts department may also be purchased to personalize the decoration. Participants need to supply own pruners and gloves. 10AM – 12PM

Holiday Marketplace at Berkshire Botanical Garden
The Garden transforms 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. 10AM – 5PM

A Christmas Carol with Gerald Charles Dickens
The great-great-grandson of the literary legend Charles Dickens, British actor Gerald Charles Dickens, will present a one-man theatrical performance of his ancestor’s classic work A Christmas Carol. An elegant Victorian tea will follow. 3:30PM

Williamstown Holiday Walk
Holiday sounds and spirit will fill Spring Street with traditional New England flair: old-fashioned caroling, horse-drawn carriage rides, a Reindog Parade, a Penny Social, Santa Claus, and much more. 9AM – 6PM

Mistletoe & Martini Cabaret Train Ride
A holiday train ride on the Berkshire Scenic Railway-Hoosac Valley Service with live music by Sam and Ron, and BYO beverages and snacks. Adults only. 6:30PM – 7:30PM.

December 8
Holiday Marketplace at Berkshire Botanical Garden
The Garden transforms 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. 10AM – 5PM

A Holiday Cabaret with Billy & Matt
Barrington Stage Company hosts local singer-songwriters Billy Keane and Matt Cusson join forces to kick off the holiday season right! Join them at Mr. Finn’s Cabaret for an evening of holiday songs and fun. 7PM

Handmade Holiday Festival!
Now a Berkshire winter tradition, the Handmade Holiday Festival is a curated marketplace that fills the historic Stationery Factory with nearly 70 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. 10AM – 3PM

A Christmas Carol with Gerald Charles Dickens
The great-great-grandson of the literary legend Charles Dickens, British actor Gerald Charles Dickens, will present a one-man theatrical performance of his ancestor’s classic work A Christmas Carol. An elegant Victorian tea will follow. 3:30PM

Your Choice Holiday Workshop
Ward’s Nursery staff help you create your own Holiday Kissing Ball or Boxwood Tree. A fragrant craft of fresh boxwood dresses porches or tabletops through the holidays. Unique ornaments from Ward’s holiday crafts department may also be purchased to personalize the decoration. Participants need to supply own pruners and gloves. 10AM – 12PM

December 14
Holiday Shindy
Holiday Shindy features strikingly accomplished artisans selling their wares in the majestic setting of what is the newly instated United American Muslim Association of the Berkshires (formally Shire City Sanctuary). This year we continue our tradition with an intimate shopping experience of 40 vendors hand selected for their unique and distinctive offerings. 10AM – 5PM

Holiday Shop, Sip & Stroll
Downtown Great Barrington with a central bonfire, holiday music, a food court, raffles and more! 4PM – 8:30PM

Family & Friends Craft Fair
The Outlet @ Pine Cone Hill is hosting its annual Family & Friends Craft inside the Outlet store. Fourteen crafters will share the fruits of their labors including beautifully scented handmade soaps, creative soft creatures, wreaths and kissing balls, jewelry and beaded boxes, fun and useful fabric storage bins, jams, tea towels and napkins, knitted hats and gloves and more. Hot drinks and snacks will welcome shoppers as well as 20% off Outlet store purchases for anyone who buys something from a crafter. 10AM – 4PM.

Murder Mystery Dinner: Grandma Got Runned Over by a…Oh Dear!
Join in the fun for this murder mystery dinner at Ventfort Hall!  Sandy Klawes has invited the family to a get together at their compound in Northpole Springs, Tennessee. It is your typical Family get together with Road Kill Casserole and Grandpa’s “special” beverage in his mason jars hidden in the cellar. Believe it or not, someone doesn’t get along with everyone and someone ends the season celebrating permanently. Come along and help figure out who dunnit. Dinner and cash bar. 5PM – 8PM

Mistletoe & Martini Cabaret Train Ride
A holiday train ride on the Berkshire Scenic Railway-Hoosac Valley Service with live music by Sam and Ron, and BYO beverages and snacks. Adults only. 6:30PM – 7:30PM.

December 15
Holiday Shindy
Holiday Shindy features strikingly accomplished artisans selling their wares in the majestic setting of what is the newly instated United American Muslim Association of the Berkshires (formally Shire City Sanctuary). This year we continue our tradition with an intimate shopping experience of 40 vendors hand selected for their unique and distinctive offerings. 10AM – 5PM

Berkshire Grown Holiday Farmers’ Market, Williamstown
Shop for all your Thanksgiving menu items at our Holiday Farmers’ Market and find your favorite farmers and vendors! Fun activities for kids, food for breakfast and lunch and live music. Admission is free. At Williams College Towne Field House, Williamstown. 10AM – 2PM.

The Nutcracker at The Clark
Snowflakes and sugar plum fantasies come to life in this encore HD broadcast of the exquisite Bolshoi Ballet production of Tchaikovsky’s beloved seasonal treat, The Nutcracker. Sweeten the holiday fun by starting the afternoon at the Sugar Plum Fairy Tea Party, featuring sweet and savory treats, hot chocolate, tea, or coffee. 2PM – 4:15PM

December 21
Mistletoe & Martini Cabaret Train Ride
A holiday train ride on the Berkshire Scenic Railway-Hoosac Valley Service with live music by Sam and Ron, and BYO beverages and snacks. Adults only. 6:30PM – 7:30PM.

Holiday Concert with Samantha Talora & Ron Ramsay at The Mount
Two of the Berkshires favorite performers, Samantha Talora and Ron Ramsay, are filling The Mount with holiday cheer! Talora and Ramsay will be performing holiday favorites throughout the afternoon. We encourage you to sign-along! Included with admission. 2PM

December 22
The Nutcracker at The Clark
Snowflakes and sugar plum fantasies come to life in this encore HD broadcast of the exquisite Bolshoi Ballet production of Tchaikovsky’s beloved seasonal treat, The Nutcracker. 1PM – 4:00PM

December 31
The Magic of David Hall
Ring in the New Year with Berkshire Museum! Join Boston-based magician David Hall as he performs amazing magic and astonishing illusions. Refreshments will be served in the Crane Room at noon. 11AM – 12PM & 1PM – 2PM.

Blantyre New Year’s Eve Gala
Yeah Baby! Ring in 2020 with Black Tie or Austin Powers style. Food stations, cocktails, dancing and a midnight champagne toast. Call for tickets!

Bach at New Year’s
“Bach at New Year’s” with the Berkshire Bach Ensemble, Director and Soloist Eugene Drucker, Co-Founder of the Emerson String Quartet, and Harpsichordist Kenneth Weiss, performing Johann Sebastian Bach’s Six Brandenburg Concerti. Celebrate the New Year in Style! At Mahaiwe Performing Arts Center, Great Barrington, MA. 6PM – 9PM

New Year’s Eve at the Colonial Theatre with Max Creek
Max Creek has reached its fourth decade of playing music, and you’d be hard pressed to find a music fan in the Northeast that hasn’t heard of them. Creek’s style lacks pretense; there is no genre title that can define them. From the beginning, they mixed rock, country, reggae, soul, jazz and calypso in with their own great songwriting, and it all comes out sounding like Creek. 8:30PM – 10:30PM

New Year’s Eve Bash
Ring in the New Year at The Stationary Factory with Whiskey City, dinner, dancing, games and more! 6pm – 12:30AM