Visitors to the Berkshires often think of our area as a summer and fall destination, when our thriving arts scene and stunning foliage draw thousands to enjoy everything our towns have to offer. As your local area experts, we’re happy to remind new and old year-round residents that winter is a stunning season in Berkshire County!
Between the 4 p.m. sunsets and shoveling of driveways, it can be hard to get the motivation to leave the house during our snowy winter months. We’ve gathered up a list of our favorite seasonal activities–trust us, they’re worth the trip!
1. Take in the Berkshire’s Best Winter Lights
While you could certainly hop into your car and make an evening of checking out your neighbor’s festive displays, there are a few Berkshire attractions that really make this time of year glow. No holiday season is complete without them!
Festival of Trees in Pittsfield
Are you looking to get to know your neighbors in the Berkshires? The Festival of Trees features a variety of displays, and each is decorated by a different home-grown business or organization. In order to earn their display at the Berkshire Museum, tree-decorating participants must work their design around a selected theme.
This year’s theme is “Barn to be Wild,” an homage to the exhibition’s temporary home at Hancock Shaker Village (the Berkshire Museum has been closed for all of 2025 while undergoing renovations). You’ll be able to say hello to the barn animals during your visit to the village!
Winterlights at Naumkeag
Winterlights at Naumkeag, a historical estate in Stockbridge, is a relatively new tradition. In the time since its launch in 2018, this grand display of holiday lights has become a popular event for all ages.
Naumkeag is a Berkshire Cottage; the 44-room home was built in the Gilded Age and retains an expansive garden along its 48-acre property. Winterlights is a display created by wrapping up Naumkeag’s gardens in thousands of colorful lights. It’s a great evening for bundling up, buying a hot chocolate, and taking part in the art by writing down your wish for the new year.
A friendly word of advice: This is a massively popular event, so you have to buy your tickets in advance, and tickets can sell out quickly!
Nightwood at The Mount
If Winterlights is “classic, warm holiday,” then Nightwood at The Mount is its slightly moody, artistic cousin. This display is also centered around a historic estate—The Mount is another Gilded Age mansion that was once home to Edith Wharton, and is another chance to take an evening stroll through a stunning expanse of now-public gardens.
As opposed to a vast array of your classic string lights, the trees of Nightwood are presented with a more theatrical light and ambient, cinematic sound. And if you celebrate Chanukah, The Mount adds a menorah lighting to their everyday festival of lights on Dec. 14 this year.
2. Visit with Santa on a Scenic Train Ride
Is there a kid in your life who can’t wait for the Polar Express to show up outside their door? Invite them for a ride on the Tinseliner, which runs for select dates courtesy of the Berkshire Scenic Railway Museum.
The short, scenic ride takes off from the town of Adams. While on board, guests can take in the festive decorations, write letters to Santa, and even meet St. Nick himself.
3. Explore a Berkshire County Ski Resort
Berkshire locals know that the best way to fight off the winter blues is to find an activity that gets you active & outside during the colder months. Luckily, we have a wide variety of ski areas with lots to offer!
Jiminy Peak
Located in Hancock, Jiminy Peak is the largest ski and snowboarding resort on this list. Like many on this list, Jiminy Peak offers night skiing–locals can clock out of work and get on the mountain until 10 p.m..
Besides its downhill trails, Jiminy offers live music in its bar and restaurant, Christiansen’s Tavern. Non-skiers can also explore the mountain’s snowshoeing trails or take a breezy ride in the Alpine Mountain Coaster on the weekends.
Catamount and Berkshire East
Heading south, Catamount sits on the border of Egremont, Massachusetts and Hillsdale, New York. Berkshire East, conversely, is near the Vermont border in Charlemont.
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If you live between the two mountains and want a little variety, riders can enjoy both mountains on the same pass.
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Both offer slightly more limited night skiing (until 9 p.m. or so on the weekends, and only for select months of the season).
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Both have an alpine skiing team for kids to learn, improve, and compete.
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All ages can ride a magic carpet up into their snow tubing park on the weekends. Note: It’s best to reserve a ride ahead of time, as availability is limited.
Bousquet
Located in Pittsfield, Bousquet is a great place for skiers and snowboarders that are looking for a social community.
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The mountain is a popular place for parents to send their children to learn to ski, as well as compete.
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They have daily lessons for adult newcomers, as well as weekly adult races through their B.A.R. league (Bosquet Adult Racing).
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Bousquet has made a significant effort to appeal to park riders with specific park lessons and yearly rail jams.
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Events include live music, DJs, and special theme nights meant for breaking out your 80’s snow gear!
If you don't ski or snowboard, Bousquet Sport across the street has plenty of fitness offerings, like pickleball, pilates, and golf training.
Notchview (Nordic Skiing)
While many of our mountains are known for alpine skiing, Berkshire County as a whole contains some great hotspots for nordic skiing as well. Notchview in Windsor is beloved for its 25 miles of cross-country skiing and snowshoeing trails. Step inside The Budd Visitor center to warm up, grab a snack, or even rent some equipment.
4. Stroll a Scenic Downtown’s Holiday Event
Lots of towns in the Berkshires put on a winter celebration for the community to come together. We’ve picked some of our favorites across the county to highlight:
Williamstown Holiday Walk Weekend
Williamstown’s holiday festivities span the entire weekend, taking place from December 5 to December 7 this year. The event kicks off with a tree lighting, live music, and a fashion show, with lots of family-friendly activities taking place all day on Saturday and Sunday—including opportunities to eat breakfast with Santa!
Great Barrington Holiday Shop, Sip, & Stroll
The Southern Berkshire Chamber of Commerce programs an afternoon and evening full of late-night shopping opportunities, kid’s and adult’s crafts, and more throughout downtown Great Barrington. This year’s stroll starts at 3 p.m. with a family hour on December 13, and finishes with a Menorah, Kinara & Tree Lighting, followed by fireworks around 7 p.m..
Stockbridge Main Street at Christmas
Stockbridge’s holiday festivities borrow their name from the 1967 painting by Norman Rockwell. On December 7, the main event is a recreation of this locally-treasured work of art, featuring antique cars lined up as they appear in the painting.
Downtown Pittsfield Festive Frolic
Pittsfield’s holiday festivities will take place across the weekend on December 5 and 6. Events on the menu include Friday’s tree lighting, an opportunity to find locally-crafted gifts at The Berkshire Bazaar, and a wreath art auction.
5. Catch a Cozy Movie at a Local Theatre
Our local movie theatres have fantastic programming year round, and they know that viewers want a bit of nostalgia during the holiday season.
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Mahaiwe Performing Arts Center: You’ll find Mickey’s Christmas Carol (1983) and It’s a Wonderful Life (1946) on their December schedule, both offered for free!
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Images Cinema: They invite you to stop in for screenings of Elf (2003) or for “Cocoa and Cartoons” during Williamstown’s Holiday Walk Weekend. Later in December, you can see A Muppet Christmas Carol (1992), White Christmas (1954), and multiple show dates for It’s a Wonderful Life (1946).
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Beacon Cinema: For one week in December, attendees can see A Christmas Story (1983) for just $1 a ticket.
6. See What’s on a Local Stage (Not During Summer Stock)
Those who leave the area as the leaves start to fall may not be aware that our performing arts venues have some incredible shows on their winter schedule as well!
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A Guaraldi Holiday at Mahaiwe Performing Arts Center: Pianist and composer Isaiah J. Thompson will play through his album A Guaraldi Holiday in the new, intimate Indigo Room.
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Berkshire Theatre Group’s Annual Holiday Shows: A Christmas Carol always finds its way to the Unicorn Theatre, which even provides a special sensory-friendly show date! The Colonial Theatre brings back Albany Berkshire Ballet’s The Nutcracker, the dog show “Mutts Gone Nuts,” and rock opera band The Wizards of Winter this year as well.
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Sense and Sensibility at Shakespeare & Company: The company takes a break from the Bard each winter to stage a work inspired by the world of Jane Austen, this year performing Kate Hamill’s telling of Sense and Sensibility.
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Stella Cole at the Tanglewood Learning Institute (TLI): While best known as the summer home of the Boston Symphony Orchestra, there’s programming at Tanglewood to enjoy year round. TLI has ongoing programming for lovers of jazz and chamber music. On December 13, viral jazz singer Stella Cole will sing plenty of timeless classics.
7. Find a Unique Gift at a Holiday Maker Market
The Berkshires are full of skilled artisans, and pop-up bazaars happen all the time. They serve as a chance to help support a local business, and give someone you love a truly unique and thoughtful gift!
Some upcoming markets include:
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Greylock Works in North Adams: FESTIVE Holiday Market on Saturday, November 22
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Holiday Inn in Pittsfield: Berkshire Bazaar by Thistle n’ Thorn Floral on Saturday, December 6
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Berkshire Botanical Garden in Stockbridge: 2025 Holiday Marketplace from Friday, December 5 to Sunday, December 7
Bonus! Support a Local Charitable Organisation for Food, Clothing, and Fuel Assistance this Winter
Stone House Properties supports a variety of nonprofits with volunteer hours and donations that help our local community have a great holiday season. We hope you’ll join us in supporting some of the great organizations that you’ll find on our Giving Back page.
Are you looking for a new home for the holidays? Take a look at our exclusive listings or get in touch with us today to start your buying or selling journey!
