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Holiday Events and Tree Lightings 2023
12:15PM / Saturday, November 18, 2023
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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. 26, 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. 3, at 6 at the town center. Festival of Trees opens in Community House at 4:30 and hayrides to and from the town center begins at 5:30; Santa and refreshments will be available at Community House afterward. The Festival of Trees will be open in Community House weekdays. 
Clarksburg: Peter A. Cook VFW Post 9144 sponsors this year's tree lighting ceremony at PFC Peter A. Cook Veterans Memorial Field on Sunday, Nov. 26, at 6 p.m. The Clarksburg Volunteer Fire Company will be bringing Santa Claus to the event to greet the children. The post will be making its annual donations at this time. 
Dalton: Festivities begin at 5 on Saturday, Dec. 9, and conclude with the tree lighting at 8. Santa will be making stops around town. 

Great Barrington: Lightings of the town tree and menorah on Saturday, Dec. 9, at 7 p.m. at Town Hall followed by fireworks. Part of the Shop, Sip & Stroll in the downtown that features crafts, music, hayrides and Santa. 

Lanesborough: The tree lighting is Thursday, Dec. 7, at 6 p.m. at the old Lanesborough Police Department on the corner of Church Street and Route 7. The school chorus will perform and there will be a free concession stand. 

Lenox: Tree lighting in Lilac Park takes place Friday, Dec. 1, 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. Hot chocolate and cookies will be available and bring a letter for Santa. Letters can be dropped off at the center through Sunday, Dec. 11.  

North Adams: Annual event returns on Wednesday, Nov. 22, at 5:30 p.m. at Monument Square. Santa Claus will arrive on the fire engine and give out goody bags. Drury band will perform. 

The annual menorah lighting will be held beginning at 5:30 p.m. on Thursday, Dec. 7. The brief ceremony will be held in the City Hall lobby with Rabbi Rachel Barenblat sharing a few words to mark the start of the Hanukkah.
Readsboro, Vt.: The town holds its 25th annual tree lighting on Wednesday, Nov. 22,  from 5 to 6 p.m at the bandstand. Sing carols and then have refreshments at the library. 

Pittsfield: The tree lighting ceremony will begin at Friday, Dec. 1, at 6 p.m. with at Park Square. Hot chocolate and candy canes will be available and Santa and Mrs. Claus will arrive to ring in the holiday season. Bring a nonperishable food item for the Christian Center's food pantry.

Tyler Street Lab hosts a Kwanzaa celebration on Friday, Dec. 29, beginning at 6 p.m. Hosted by the Women of Color Giving Circle and ROPE.

Pownal, Vt.: Tree lighting at Town Hall on Saturday, Dec. 2, at 5 p.m. The festivities start with face painting, the school chorus, hot cocoa and cookies, from 3:30 to 4:30, when Santa arrives. The lighting is dedicated to Dick Singleton. Bring a non-perishable item for the food pantry. 

Williamstown: the tree at the Williams Inn will be lighted on Saturday, Dec. 2, at 5 p.m., accompanied by caroling. Part of the annual Holiday Walk. 

South Williamstown Community Association hosts a tree lighting on Sunday, Dec. 10, at  5 p.m. at the Store at Five Corners. There will be carol singing, refreshments provided by the store and Santa. Bring a flashlight to read the song sheets that will be provided.
The menorah candle will be lighted for the first night of Hannukah on the lawn at the Williams Inn on Thursday, Dec. 7, at 4:30 p.m. Rabbi Rachel Barenblat and Rabbi Seth Wax will lead the outdoor service. People of all ages, faiths, and backgrounds are invited to attend.

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. 3, from 4:30 to 6 p.m. Join the parade from Congregational Church to Town Hall for music, the tree lighting, and gifts from Santa. 

Stephentown, N.Y.: Lighted parade and tree lighting on Saturday, Nov. 25. Lighted tractors, side-by-sides, floats, fire trucks and cars, and marching groups step off at 5:30 from the Fire Hall to the Veterans Park for the tree lighting.

Popcorn and hot cocoa will be available at the fire station on NY 43, which will also accept unwrapped toys for the annual toy drive. New this year is the offering of hamburgers and hot dogs at the fire station from 4 to 5:30 p.m.  

Holiday Events

Adams: The Tinseliner Train returns with Santa, caroling and more. The Hoosac Valley Line runs the scenic Christmas train rides weekends through Dec. 17. Tickets from $3 to $25; more information here

The Eagle Band's brass ensemble performs its 9th annual Holiday Music Concert in the GAR Memorial at the Adams Free Library on Sunday, Dec. 3, at 3 p.m. The free performance is presented by the Adams Historical Society. Elevator entrance is off Melrose Street. 

Great Barrington: Southern Berkshire Chamber's Holiday Shop, Sip & Stroll runs Saturday, Dec. 9, in downtown Great Barrington from 3 to 8 p.m. More information here. 

Lenox: NightWood, a light, sound, and color event, runs at The Mount through Jan. 6. Admission is $12 to $25 per person; register here.

North Adams: First Friday Festivities  on Friday, Dec. 1, include self-guided tours of the LumiNAMA displays throughout the downtown (Awards gala Dec. 16), a winter market, carriage rides, art experiences and a gingerbread celebration. A Holiday Music Tour is set for Sunday, Dec. 10, from noon to 9 at various venues. 

Stockbridge: Stockbridge Main Street at Christmas runs Friday to Sunday, Dec. 1-3, with a range of holiday activities including live performances, historic property tours, holiday markets, shops, restaurants and Santa. On Sunday, the town re-enacts the spirit of Norman Rockwell's famous holiday scene from noon to 2. More information here.
Naumkeag's Winterlights runs through Jan. 7; tickets are limited here. Berkshire Botanical holds its annual Holiday Market on Friday through Sunday, Dec. 8-10. More information here.

Williamstown: The Williamstown Chamber's annual Holiday Walk runs Saturday and Sunday, Dec. 2 and 3, with the popular Reindog Parade at 2 p.m. on Saturday. Activities include breakfast with Santa in the Williams Inn ballroom, 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

The Police Department hosts its annual holiday open house on Saturday, Dec. 16, from 4 to 6 p.m.

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