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2024 Holiday Event Guide

Let’s get straight to it! There is so much to look forward to this holiday season in the Berkshires. Here’s a list of our favorites. 


*denotes a free event!


Festival of Trees: Aquatica at Berkshire Museum

Pittsfield MA


2024 marks the 40th year of the Festival of Trees! Included with museum admission, visitors can enjoy trees decorated by local businesses, students, museum staff and more. This year's Aquatica theme is all about the ocean, rivers, and wetlands. An opening reception will take place Friday, November 22 from 5:30 - 8 p.m. Information here!


Friday, November 22 through Sunday, January 5


Holiday Lights!

Lenox and Stockbridge, MA


There is nothing like the twinkle of holiday lights to make those long winter nights cozy and festive. Check out two great options below:


Friday, November 22 through Saturday, January 4 from 5-8 p.m.


Friday, November 29 through Saturday, January 4 from 4:30-8 p.m.


Friday, December 7 through Tuesday, December 31 from 5-8 p.m.

Thanksgiving on the Farm at Hancock Shaker Village

Pittsfield, MA


Fill your Thanksgiving weekend with extra family fun at Hancock Shaker Village. Events begin Friday and include guided walks, a Shop and Sip, a Shaker Music Program and more! Check out their entire calendar of events here.


Friday, November 29 - Sunday, December 1


Holiday Movies at the Mahaiwe*

Great Barrington, MA 


Mahaiwe Performing Arts Center has been in operation for almost 120 years! Check out their holiday movie series for family fun this November and December. Click the titles for times and tickets!


Saturday, November 30: Wizard of Oz 

Friday, December 13: How the Grinch Stole Christmas 

Saturday, December 14: Olaf’s Frozen Adventure (Free Event!) 

Friday, December 20: It’s a Wonderful Life (Free Event!) 


Christmas at Chesterwood

Stockbridge, MA


Here in the Berkshires, we love events at quant summer Gilded Age cottages like Chesterwood. Once home to sculptor Daniel Chester French, this beautiful estate has been a National Historical Landmark since 1965. Visit Chesterwood this season to hear stories of the French family’s Christmas traditions with hot cider and doughnuts. Purchase tickets here.


Sundays, Fridays and Saturdays in December


Holiday Shop Hop and Tree Lighting*

Lee, MA


Events in downtown Lee feel like they’re straight out of Gilmore Girls. There’s nothing like a stroll down Main Street! Businesses will extend their hours so you can enjoy all they have to offer into the evening. The tree lighting begins at 6 p.m. in the park! More here.


Friday, December 6 from 3 - 8 p.m. 


Festive Frolic*

Pittsfield, MA 


From tree lighting and hot chocolate to a holiday market and paint & sip, there is something for everyone at Pittsfield’s Festive Frolic. Learn more about the event here!


Friday, December 6 and Saturday, December 7


Holiday Marketplace at Berkshire Botanical Garden*

Stockbridge, MA 


This weekend-long tradition continues in December. The festivities kick off Friday evening with the Holiday Wreath Preview Party, featuring a silent auction, live music and more. The marketplace is open from 10 a.m. through 4 p.m. on Saturday and Sunday. Read all about it here!


Friday, December 6 through Sunday, December 8 


Williamstown Holiday Walk

Williamstown, MA


There is so much to do in Williamstown this December! Check out the links below from Destination Williamstown for a full rundown. In addition to hosting numerous events, many downtown businesses are also collecting items like non-perishable foods, toys, mittens and more. Friday, Saturday and Sunday events! 


Friday, December 6 through Sunday, December 8

Holiday Trivia at The Foundry* 

West Stockbridge, MA


Get ready for the Holiday Season with trivia on Christmas, Hanukkah and Kwanzaa. Cocktails, costumes, and cheer! This event is free, but they suggest a $15 donation to the West Stockbridge Public Library. And Berkshires BFF LOVES libraries! Tickets here.


Wednesday, December 11 at 7 p.m. 


Winter Starts Here Concert and Party at Bousquet Mountain*

Pittsfield, MA 


For our cold-weather lovers, be sure to check out the winter kick off event at Bousquet! There will be live music and a special appearance by Santa himself. More details here!


Saturday, December 14 from 12 - 5 p.m.


Jewish Federation of the Berkshires Events*

All over Berkshire County, MA


Did you know there are more than 20 different ways to spell Hanukkah? While the festival of lights doesn’t begin until December 25 this year, the Jewish Federation of the Berkshires has plenty of events to get you in the holiday spirit. Tickets and times are linked on the event titles! 


Sunday, December 15: PJ Library Hanukkah Party


Berkshire County Historical Society Events*

Pittsfield, MA


For local history lovers who are searching for a holiday event, be sure to check out what BCHS has in store for us this season:


Sunday, December 15: Holiday Tea at Arrowhead


Happy Holidays from Berkshires BFF!

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