Holiday Events and Tree Lightings 2025| 12:15PM / Saturday, November 22, 2025 | |
This year's holiday gatherings and annual tree lightings are being announced Here's what we have so far in events below. If we're missing any, let us know at info@iBerkshires.com.
Visit our Holiday Bazaars and Craft Fairs list for holiday craft fairs and markets.
Christmas Tree Lightings
Adams: There will be a tree lighting and a visit from Santa and Mrs. Claus on Sunday, Nov. 30 at the Adams Town Common. The celebration begins at 2, featuring hayrides, music by DJ Bizz, hot chocolate courtesy of The Daily Grind, candy from the Adams Lions Club, and a special visit from Santa and Mrs. Claus. The official tree lighting will take place at dusk, around 4:30.
A second Holly Days event will be held on Dec. 6, featuring a campfire, children’s activities, and another visit from Santa, sponsored by Adams Community Bank.
Cheshire: Annual tree lighting is Sunday, Dec. 7, at 6 at the town center. Festival of Trees opens in Community House at 4:30 and a hayride to the town center is at 5:30; Santa and refreshments will be available at Community House afterward. Additional hours will be posted to view the Festival of Trees through the holiday season. There will be a bonfire, caroling, cookies and cocoa, raffles and and sales of adult refreshments.
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. 30, at 6 p.m. The Clarksburg Volunteer Fire Company will be bringing Santa Claus to the event to greet the children.
Dalton: The town will be celebrating the holiday season with the annual Light up the Holidays event on Saturday, Dec. 6 starting at 5 p.m. Santa will stops around town to greet families participating in festive activities. The event will conclude with a tree lighting at 8 in front of the Community Recreation Association.
Great Barrington: Lighting of the town tree is on Saturday, Dec. 13, at 7 p.m. at Town Hall. Part of the Shop, Sip & Stroll in the downtown that features crafts, music, activities, hayrides and Santa.
Hancock: The Christmas tree lighting with Santa is on Saturday, Dec. 29, at 6 p.m. at Town Hall.
Lanesborough: The tree lighting is Thursday, Dec. 5, 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.
Lee: Tree lighting is Saturday, Dec. 6, at 5 p.m. in Church Park. Holiday music, carols, cookies and hot cocoa. Sponsored by Henry's Electric and the Lee Chamber of Commerce. The chamber will be selling $5 remembrance angels to benefit the Lee Food Pantry and Laliberte Toy Fund. More information here.
Lenox: Tree lighting in Lilac Park takes place Friday, Dec. 5, by 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 at the center. Hot chocolate and cookies will be available and bring a letter for Santa.
North Adams: Annual event returns on Wednesday, Nov. 26, 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 p.m. on Wednesday, Dec. 25. 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.
Pittsfield: The tree lighting ceremony will begin at Friday, Dec. 5, at 6 p.m. at Park Square as part of Downtown Pittsfield Inc.'s Festive Frolic. Hot chocolate by Lipton Market 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.
The Pittsfield High School Chorus will perform carols around 5:45 p.m. and artists Peter Vacchina and Robert Markey will be creating holiday-themed ice sculptures in the park. Otto's Kitchen & Comfort will also host a free hot chocolate bar and photos with the Grinch.
Pownal, Vt.: Tree lighting at Town Hall on Saturday, Dec. 6, at 5 p.m. The festivities start at 4 with school chorus, reading, singing, hot cocoa and cookies, and Santa. Bring a non-perishable item for the food pantry.
Readsboro, Vt.: The town holds its annual tree lighting on Thursday, Dec. 4, at 5 p.m. at the bandstand.
Stephentown, N.Y.: The Stephentown Volunteer Fire Department will be holding its annual Lighted Parade & Tree Lighting on Saturday, Nov. 29. The tree lighting and parade line up will begin at 4 p.m. at Cinch Em Up Stables at Route 43; the parade rolls off after the tree lighting at 5:30 and proceeds to the fire station for cookies and hot cocoa with Mr. and Mrs. Claus.
The station will have hot dogs, hamburgers, drinks and kettle corn for sale beginning at 4. The department will be accepting unwrapped toys for the annual toy drive.
Washington: The annual lighting of the town's tree will be in the town park on Saturday, Dec. 7, at 5:30 p.m. with hot cocoa and caroling.
West Stockbridge: The annual "Sparkles" event hosted by the town's Parks & Recreation will be held on Friday, Dec. 5, from 4:30 to 6 p.m., with the tree lighting at 5.
Williamstown: the tree at the Williams Inn will be lighted on Saturday, Dec. 6, at 5 p.m., accompanied by caroling. Part of the annual Holiday Walk.
South Williamstown Community Association hosts a tree lighting on Sunday, Dec. 7, 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.
Sweetwood of Williamstown hosts a tree lighting on Friday, Dec. 5, at 4 p.m.
The menorah candle will be lit for the first night of Hannukah on the lawn at the Williams Inn on Monday, Dec. 15 at 5:45 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.
Holiday Events
'A Christmas Carol'
A touring production of five actors will play the full cast of characters from Dickens' "A Christmas Carol." A portion of the proceeds will go the Trevor Project. Performances are at 7 p.m. at Hot Plate Brewing in Pittsfield on Dec. 11; Common Folk at 165 East Main St., North Adams, on De. 12; Rosasco's Fine Art Gallery, 12 Holden St., North Adams on Dec. 13; and at the Dalton Free Library on Dec. 14.
More information and tickets here.
Adams: The Tinseliner Train returns with Santa, caroling and more. The Hoosac Valley Line runs the scenic Christmas train rides weekends from Nov. 29 through Dec. 14. Tickets from $5 to $25; more information here.
Eagles Band performs a Holiday Concert from 3 to 6 p.m. on Sunday, Nov. 30, in the GAR Hall in the Adams Free Library.
Berkshire Lyric will perform "In Dulci Jubilo" on Sunday, Dec. 14, at 3 p.m. at at Saint James Place on Main Street featuring traditional and contemporary a cappella carols. Tickets are $20 at the door, with children and students 18 and under admitted for free. Tickets are $35. For further information, or to purchase tickets in advance, visit www.BerkshireLyric.org.
Lenox: Winterland starts Friday, Dec. 6, from 4 to 6 with a walk, downtown shopping and tree lighting. Events will continue on Saturdays, Dec. 7 & 14, with shopping, crafts and Santa. See more information here.
NightWood, a light, sound, and color event, runs at The Mount from Nov. 22 through Jan. 6. Admission is $12 to $27 per person; register here. Lenox Community Night is Dec. 5.
North Adams: First Friday Festivities on Friday, Dec. 6, include self-guided tours of the LumiNAMA displays throughout the downtown, gallery openings, and shopping specials.
Pittsfield: The Eagle Band's brass ensemble performs its 10th annual Holiday Music Concert at First United Methodist Church on Sunday, Dec. 13, at 3 p.m.
Berkshire Lyric will perform "In Dulci Jubilo" on Friday, Dec. 12, at 7:30 p.m. at St. Mark's Church on West Street featuring traditional and contemporary a cappella carols. Tickets are $20 at the door, with children and students 18 and younger admitted for free. For further information, or to purchase tickets in advance, visit www.BerkshireLyric.org.
Stockbridge: Stockbridge Main Street at Christmas runs Friday to Sunday, Dec. 6-8, 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 and tickets here.
Berkshire Lyric presents "The Most Wonderful Time of the Year," a concern of traditional and contemporary carols and well-known standards from the American holiday songbook, on Saturday, Dec. 20, at 4 in Stockbridge Congregational Church on Main Street. Santa will also make an appearance at this event geared for children. Tickets are $20, with children 18 and younger admitted for free thanks to the support of The Red Lion Inn. For further information, or to purchase tickets in advance, visit www.BerkshireLyric.org.
Williamstown: The Williamstown Chamber's annual Holiday Walk runs Saturday and Sunday, Dec. 6 and 7, with the popular Reindog Parade at 2 p.m. on Saturday. Activities, including some events Friday night, 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 1753 House Committee and the Williamstown Historical Museum invite the community to the annual 1753 House Carol Sing on Sunday, Dec. 22, at 7 p.m. The event is a free, ecumenical event for all ages. Deborah Burns will lead the a cappella singing beside a roaring blaze in the fireplace. Hot mulled cider, donated by Provisions, and carol books are provided. There is no heat or electricity in the 1753 House, so dress warmly and bring a light to see by. Parking is available at the library.
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