Weekend Outlook: Jolly HolidayBy Breanna Steele, iBerkshires Staff
10:21AM / Thursday, December 04, 2025 | |
Check out the activities happening this weekend around the county including many holiday-themed events like Santa meet and greets, and some Christmas tree lightings. Find all the craft fairs and bazaars happening here.
Editor's Pick
Holly Jolly Holiday
Holiday Brook Farm, Dalton
Time: Saturday, 11 a.m. to 3 p.m.
Visit the farm for hot chocolate, wreath decorating, kids crafts, animals, wagon rides, and local gifts. Families will also have the opportunity to meet Santa and Mrs. Claus and take a photo.
More information here.
Multiple Days
Downtown Pittsfield Festive Frolic
Downtown Pittsfield
Friday and Saturday
There will be many holiday-themed events happening, including Pittsfield's tree lighting at Park Square on Friday night. Bring the family to enjoy many events at your favorite local vendors, including photo opportunities with Santa himself.
More information on all of the events here.
Tinseliner Scenic Christmas Train
3 Hoosac St., Adams
Dec, 6,7,13 and 14
Meet Santa and Mrs. Claus while enjoying a festive ride on the train featuring holiday music and writing letters to Santa. More information and tickets here.
Nightwood
The Mount, Lenox
Dec. 6, 12, 13, 18-23, 26-31
The Mount has decked out its grounds for the annual Nightwood installation with lights and music to provide an immersive experience to its visitors.
More information here.
Festival of Trees
Hancock Shaker Village, Pittsfield
Every Friday Through Sunday until Dec. 28
The historic Hancock Shaker Village will welcome visitors to gaze at more than 75 trees throughout the museum grounds, culminating in a magical display at the iconic Round Stone Barn.
Tickets are $20. Children 12 and younger are always free. Berkshire Museum and Hancock Shaker Village members are free. More information here.
Williamstown Holiday Walk
Downtown Williamstown
Friday evening through Sunday
Events include caroling, runway shoes, shopping specials, films, crafts and more, plus the ever-popular Reindog Parade on Saturday afternoon.
Read our preview here.
Friday
North Adams First Friday
Downtown North Adams
Time: 5 to 9 p.m.
This month's theme is to celebrate LumiNAMA. Bring your family and enjoy a free photo with the "Hatchlings" in the Eagle Street Parklet and enjoy free face painting. There will be live music, food, craft night, and more.
More information here.
Berkshire Music School Benefit Concert
Adams Theater, Park Street
Time: 6 p.m.
A collaboration between the Berkshire Music School and Adams Theater featuring Samirah Evans and Nate Martel, and performances by music school students and faculty.
Tickets are $35; all proceeds benefit Berkshire Music School. More information here.
Holiday Wreath Making
The Plant Connector, North Adams
Time: 6 to 8 p.m.
Want your own holiday wreath this year? You can either decorate a pre-made wreath or start from scratch. Get into the holiday spirit with a fancy wreath made by you to showcase off your own door or as a perfect gift for someone else. Tickets are $55, all materials included.
More information and tickets here.
Free Hot Chocolate and a Photo Op with The Grinch
Otto's Kitchen and Comfort, Pittsfield
Time: 5 to 8 p.m.
After Pittsfield tree lighting, stop by Otto's tp warm up with some hot chocolate and meet the Grinch for a picture.
More information here.
Saturday
Holly Days
Adams Visitor Center
Time: 2:30 to 4:30
Celebrate the holidays with hot chocolate s'mores, and the chance to meet Santa at 3 p.m. There will be various activities for children to enjoy.
More information here.
Photos with Santa
Clarksburg Fire Station, Cross Road
Time: 10 a.m. to 1 p.m.
Meet Santa and get a professional picture perfect for your holiday cards. Cost is $20; free coffee and hot cocoa. More information here.
Wreath Art Auction
Lichtenstein Center for the Arts, Pittsfield
Time: 4 to 6 p.m.
Dozens of local artists are participating in the 11th annual Wreath Art Auction to benefit the Pittsfield Community Food Pantry; $10 suggested donation at the door. Hosted by the Office of Cultural Development. Grab-and-go wreaths are available starting at 4 and the auction at 5:30.
Winter Wonderland at the Library
18 Main St., Lenox
Time: noon to 3 p.m.
The library is hosting family crafts including cookie decorating, button making, snowmen, and more.
More information here.
Donkey Day at the Berkshire Carousel
50 Center St., Pittsfield
Time: 2 to 4 p.m.
Take a free ride on the carousel to celebrate "Missie the Donkey," who is immortalized on the carousel. Missie accompanied local author Kevin O'Hara on his journey across Ireland 50 years ago that was chronicled in his book "Last of the Donkey Pilgrims." O'Hara will be signing books and the Scoil Rince Breifne O Ruairc Dancers will perform at 2. On Sunday, Santa will ride the carousel, also at 2 p.m.
More information here.
Sunday
Krampus Mummers Ball
283 Cole Ave., Williamstown
Time: 5 to 8 p.m.
Put on a costume and a mask to celebrate the first ever Krampus Ball. This is the time for adults to celebrate, dance and gather around the fire with some cider from the Berkshire Cider Project.
More information here.
Brunch with Santa
Wahconah Country Club, Dalton
Time: 9 a.m. to 1 p.m.
Have brunch with the man in red himself and enjoy professional photos with him before he rides back to the North Pole. You will need to make reservations at Rsvpsantabrunch@gmail.com
Cost is adults $16, children $8; photos are $25. More information here.
Farmers' Markets
North Adams Indoor Market
Hotel Downstreet
Time: Saturday, 9 to 1
Final market of the year; the indoor market runs the first Saturday of every month through May. Fresh produce, vendors and more.
| 
.jpg)
