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Holiday Events and Tree Lightings 2021
04:15PM / Monday, November 22, 2021
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This year's holiday gatherings and annual tree lightings are still feeling the effects of the novel coronavirus pandemic. Some events have been canceled or are being held virtually. Here's what we have so far in events below. If we're missing any, let us know at Reminder that many of these events and activities do require face coverings and social distancing. 

Visit our Holiday Bazaars and Craft Fairs list for holiday craft fairs and markets.

Christmas Tree Lightings

🎄 Adams: Tree lighting and a visit from Santa at the annual Holly Days on Sunday, Nov. 28, from 2 to 5 p.m. at the Town Common. Santa arrives by 3 and the tree will be lit at 5; rides, refreshments and activities. 
🎄 Cheshire: Annual tree lighting is Sunday, Dec. 5, at 5:30 at Town Hall. A hayride begins at the community center; Santa and refreshments will be available at the community center afterward
Christmas concert with Santa and Terry a La Berry on Friday, Dec. 10, at 6:30 at the community center. Admission is free; non-perishable food item suggested as donation.
🎄 Dalton: Tree lighting is Sunday, Dec. 12, at the CRA Pavilion with Santa Claus. Part of the Light Up the Holidays and Santa Wave Parade. Starting at 4 p.m., Santa visits Depot Street sidewalk, Dalton Methodist Church, St. Agnes' Church and arrives at the pavilion at 5:30. He will be accompanied by the Wahconah Regional High chorus and band for carols and singing at each stop. The wave parade begins at 6 with Santa escorted through the town. Find the times and route here. 
🎄 Great Barrington: Tree lighting on Saturday, Dec. 11, at 7 p.m. at Town Hall followed by fireworks. Part of the Shop, Sip & Stroll in the downtown. 

🎄 Lenox: Tree lighting in Lilac Park takes place Friday, Dec. 3, at 6 p.m. hosted by the Lenox Community Center. Come early for caroling with the LCC chorus at 5:45 and stay for pictures with Santa Claus in the gazebo (Santa says wear your mask). Hot chocolate and cookies will be available and bring a letter for Santa. Letters can be dropped off at the center through Sunday, Dec. 12.  

🎄 North Adams: Annual event returns on Wednesday, Nov. 24, at 6 p.m. at Monument Square. Santa Claus will arrive on the fire engine and give out goody bags. Drury band will perform. 

🕎 North Adams: The annual menorah lighting will be held beginning at 5 p.m. on Sunday, Dec. 28. The brief ceremony will be held in Dr. Arthur Rosenthal Square across from City Hall with Rabbi Rachel Barenblat sharing a few words to mark the start of the Hanukkah.

🎄 Pittsfield: Virtual tree lighting on Friday, Dec. 3, at 6 p.m. broadcast by PCTV. More information here.

🎄 Williamstown: the tree at the Williams Inn will be lighted on Saturday, Dec. 4, at 5 p.m., accompanied by caroling. Part of the annual Holiday Walk. 

🎄 West Stockbridge: A "Sparkles" event hosted by the town's Parks & Recreation, with help from the police and fire departments, will be held on Sunday, Dec. 5, at 4 p.m. Join the parade from Congregational Church to Town Hall for music, the tree lighting, and gifts from Santa. 

Holiday Events

Adams: St. Stanislaus Kostka School holds its annual bazaar on Saturday, Nov. 20. Polish food, holiday items, raffles and more.

🎅 Great Barrington: Southern Berkshire Chamber's Holiday Shop, Sip & Stroll runs Saturday, Dec. 11, in downtown Great Barrington from 4 to 7 p.m. and concludes with the tree lighting, followed by fireworks and a free performance at 7:45 by the Vocalis Youth Choir at St. James Place. 

Activities including wreath-making, gingerbread house decorating and visits with Santa, along with music, a parade and "live" windows. See the full list and times here. 

Lenox: NightWood, a light, sound, and color event, runs at The Mount through Dec. 31. Admission is $10 to $20 per person; register here.

🎅 Lenox Library's virtual Holiday Pajama Night is Saturday, Dec. 4, from 6 to 7 p.m. Pick up goodie bag at the library on Thursday or Friday between 11 and 5:30; join via Zoom on Saturday at 6 to hear stories and to listen to music by Terry a la Berry and Friends.
Stockbridge: Main Street at Christmas has been canceled this year because of rising COVID-19 cases. The town will be still be decorated and stores and cultural venues open. 
✨Naumkeag's Winterlights runs through Jan. 9; tickets are limited here. Berkshire Botanical holds its annual Holiday Market on Saturday and Sunday, Dec. 4 and 5. More information here.

Williamstown: The Williamstown Chamber's annual Holiday Walk runs Saturday and Sunday, Dec. 4 and 5, with the popular Reindog Parade at 3 p.m. on Saturday. Activities include breakfast with Santa at Ioka Valley Farm, card and wreath making, a gingerbread house exhibit, caroling, hot chocolate, photo booths, and others. Some events have admission fees or require registration. See the full list here

Wednesday, Dec. 25:

North Adams: Be Our Guest Christmas Dinner at the American Legion, 11:30 to 1, featuring ham dinner with sides, soup and dessert. All are welcome; for delivery, call 413-664-9004.


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