One of the best things about living in the Berkshires is being able to experience each and every season. If you’re willing to brave the cold, winter is one of the best for getting out and enjoying the nature, culture and community that western Massachusetts has to offer. If you’re new to the area, looking to add a new tradition to your calendar, or just in search of the perfect cup of hot chocolate–read on for the ultimate guide.
Christmas Lights and Holiday Decor in The Berkshires
Lots of neighborhoods around the county take their winter light displays very seriously; but if you prefer a walk rather than a drive around, there are a few organizations that are known for their stunning yearly displays.
Winterlights at Naumkeag
Naumkeag is one of many historic Berkshire estates that have become a scenic haven for the public to enjoy through walks, museum tours, or other special events. Perhaps the best-known of such events at Naumkeag is Winterlights, a stunning walk of twinkling lights in the estate gardens. Bundle up, grab a hot chocolate from their stand (booze optional) and don’t forget to write and hang your Christmas wish. My biggest tip when it comes to Winterlights is to buy your tickets early–this incredibly popular event is known to sell out!
NightWood at The Mount
Similar to Winterlights, NightWood is a light display at The Mount, the historic home of author Edith Wharton. But where Winterlights is classic Christmas, NightWood is a more ethereal and artistic display of lights and sound along a ¾ mile walking route. You’ll feel as though you’ve stumbled across a modern art exhibit in the woods. My agency, Stone House Properties, is proud to be one of the nine community sponsors of this event!
Festival of Trees at Berkshire Museum
If you’re not a fan of bundling up and facing the chilly evening air, Pittsfield’s Berkshire Museum has an annual tradition of creating an indoor exhibition that celebrates the season. The Festival of Trees invites the community to participate in the tradition of decorating a large collection of trees to honor the schools, businesses, organizations and individuals who make the Berkshires go ‘round. The theme for their current installment is “Nostalgia,” which is only fitting for the museum’s 120th anniversary this year.
Best Spots for Gift Shopping
No matter what you’re celebrating this year, odds are you’ll have some gift shopping on your to-do list. Luckily, the Berkshires’ craftsmen and tastemakers rise to the challenge each year with displays in year-round shops and pop-up markets. You’re bound to find something locally made and truly unique to delight your loved ones.
Great Barrington Holiday Shop, Sip and Stroll
It’s never a bad time to visit the boutiques on Great Barrington’s main drag. But when you visit during the Holiday Shop, Sip and Stroll, you’ll hear Christmas music, watch the tree lighting, and enjoy plenty of other holiday treats–potentially including a visit from Santa Claus. Plenty of shops extend their hours into the evening for this one-day event, and the Holiday market invites lots of local artisans to sell their wares from pop-up stalls. What’s more, you’ll be able to enjoy plenty of activities for both kids and adults, from letters to Santa to adult-only wreath making. It’s a perfect time to get in the spirit and pick up a gift or two while getting into the spirit of the season. The holiday stroll takes place on the first Saturday of December, making this year’s fall on December 9.
Stockbridge Main Street at Christmas
The magic of Stockbridge’s Main Street at Christmas was captured in 1967 by Norman Rockwell, and the town takes pride in preserving that nostalgic cheer each December. The Stockbridge Chamber of Commerce takes care to schedule plenty of events that celebrate the season, but it’s just as fun to wander Main Street at your own pace and visit the shops for your holiday antiques, wine, and artwork.
Unique Boutiques in Downtown Lenox
The downtown area of Lenox is one of my favorite places to walk around. There’s plenty of places to dine, drink, and shop. From home goods to one-of-a-kind clothes and accessories, it’s a great place to find gifts–my partner is partial to the combination bookstore and wine bar. And if you’re buying gifts for someone who enjoys quality time over material goods, there are some amazing restaurants in town to pick up a gift card for a meal for two.
Pop-Up Holiday Markets around the Berkshires
Even if you’re not handy yourself, you can find a gift that’s handmade with love for the people in your life at a variety of pop-up markets. At each, you’ll find collections by local makers that you’ll feel great about supporting, and you’re bound to find something a hard-to-shop-for friend doesn’t already have. You can’t go wrong at any of these markets, so I’ve listed them for you here:
Holiday Shindy
Where: Zion Lutheran Church in Pittsfield
When: Saturday, December 9 10 a.m. to 4 p.m.
Need to know: There’s a $3 entry to get into the market.
Berkshire Grown Winter Farmers Markets
Where: 1064 Main Street in Housatonic
When: Select Saturdays–December market is December 16, 10 a.m. to 2 p.m.
Need to Know: This is the market to pick up local food goods, including specialty reserves for your gift basket!
Where: Greylock WORKS in North Adams
When: Saturday, November 18, 10 a.m. to 3 p.m.
Need to Know: Pay attention to the date–this holiday market is early in the season!
Where: The Stationery Factory in Dalton
When: Saturday, November 25 11 a.m. to 5 p.m. and Sunday, November 26 10 a.m. to 3 p.m.
Need to Know: This market is put on by Roots Rising, a local nonprofit that empowers local youth through food and farming education. You’ll also enjoy music and free mimosas as you shop!
Where: The Racebrook Lodge
When: Saturday, December 2 and Sunday, December 3 from 12 p.m. to 6 p.m.
Need to Know: Lize jazz, mulled wine, and Santa Claus will all be present at this market!
Best Local Christmas Tree Farms
Is getting a real Christmas tree for your home an unmissable yearly tradition? There’s lots of local farms nearby to take the family to. Personally, I grew up chopping down our own tree at Strawberry Acres in Hinsdale. Just over the border in New York, you can either do-it-yourself or get a pre-cut tree at Ioka Valley Farm. Holiday Brook Farm, Forthill Farm and Ward’s Nursery are all great places to find pre-cut trees as well–you may even get the chance to feed some animals during your stop at Ward’s!
Staying Active Outdoors
Growing up in the Berkshires turned me into an avid skier. Even if you aren’t one for the slopes, there’s lots of ways to get out and enjoy the great outdoors once the snow starts to fall.
Best Nearby Ski Resorts
Jiminy Peak, Butternut and Bousquet Mountain are two fantastic options inside of the Berkshires to ski, snowboard, and even grab a drink and enjoy some live music once you finish. Butternut and Bousquet both have terrain parks for those who prefer to practice their tricks–and if you’re a beginner, each mountain offers a variety of lessons. Just outside of the Berkshire borders, you’ll find some other mountains in an easy day’s driving distance: including Catamount, Prospect Mountain, Stratton and Killington, to name a few.
The best part? Jiminy Peak and Bousquet both offer night skiing, which means that the ski spots within easy reach will be there for you when you get out of work–you’ll be able to get your money’s worth out of your ski pass!
Cross-Country Skiing
If ski slopes and terrain parks aren’t your type of skiing, worry not–places like local orchards, parks and farms in the area transform into a cross-country skier’s paradise when the snow comes down! Popular spots include Canterbury Farms in Becket, Hilltop Orchards in Richmond, Kennedy Park in Lenox and Notchview in Windsor.
Popular Snowshoe Trails
Many of the cross-country ski spots listed above have snowshoes to rent and trails to explore! Many avid snowshoers in the area also invest in their own pair and trek the area’s popular hiking trails. Popular easy to moderate journeys include The Boulders Reserve, Canoe Meadows, and Bash Bish Falls. Those looking for something really challenging can conquer Mount Greylock by way of Bellows Pipe Trail.
Ice Fishing
When things really start to freeze over, you’ll frequently see people ice fishing on the local lakes. Pontoosuc Lake is one of the most popular spots, but you can also expect to reel in a fish or two on Onota Lake on the Stockbridge Bowl. Just be sure to monitor the conditions careful and err to the side of caution when heading out on the ice!
Holiday Activities for Kids & Families
I can tell you from experience; Christmas in the Berkshires is magical for a kid. There’s plenty of family-oriented activities to make the holiday spirit go ‘round.
Christmas Scenic Train Rides with Santa
Do you dream about experiencing “The Polar Express” for yourself? Riding the “Tinseliner” by the Berkshire Scenic Railway Museum is just about as close as it gets. Take in the view of Hoosac Valley while you sing carols and hang out with Santa Claus. And if you’re looking for a more adult-oriented festivity, check out their “Mistletoe & Martinis Cabaret Train.”
Williamstown Holiday Walk
For 40 years, the Williamstown Holiday Walk has been a tradition where people of all ages can take in the holiday cheer and do some charitable giving. You can take in live performances from the likes of Johnny Irion, see holiday classics at Images Cinema, eat breakfast with Santa and participate in a number of holiday drives to give food, clothes, and new or used toys to those in need.
Ice Skating
Both natural rinks like frozen ponds and indoor options are easily found in the Berkshires if you like to ice skate. The Boys and Girls club offers extremely affordable open skates with rentals. Canterbury farms is another with skate rental options if you’d like to enjoy their cleared pond. If you’ve got your own skates, there’s plenty of viable pond options in the area–just make sure you’re paying attention to weather conditions before stepping out on the ice!
Classic Holiday Movies on the Big Screen
Our local movie theaters are known to bring holiday classics to the big screen for you and your family to enjoy. This year, Images Cinema in Williamstown will be playing “The Grinch” (2018), “Elf” and “It’s a Wonderful Life” during the Holiday Walk. In Pittsfield, the Beacon Cinema will play “The Polar Express”, “Dr. Seuss’s How The Grinch Stole Christmas” (2000), and “A Christmas Story.” And down south in Great Barrington, The Mahaiwe will play “The Muppet Christmas Carol,” “It’s a Wonderful Life” and “Mickey’s Christmas Carol.” They’re great events for introducing your favorite childhood films to a new generation!
Festive Fun on Local Stages
The Berkshires are known for our summer theater festivals. Our stages are filled with talent, and plenty of these actors stick around for a fun holiday show or two.
A Christmas Carol in Stockbridge
Each year, Berkshire Theatre Group puts on the classic holiday tale by Charles Dickens. The play will be onstage at The Unicorn Theatre in Stockbridge throughout the month of December. They’ve even launched a collaboration with Wintetlights a Naumkeag, so you can follow your production with a walk through the lights on the very same night! And if you have a loved one with autism or any other sensory sensitivities, there’s a special sensory-friendly showing on December 20.
Christmas at Pemberley in Lenox
Shakespeare & Company in Lenox don’t just put on plays by Shakespeare himself–but they sure know how to cater to fans of classic literature. This December, they’re putting on “Georgiana and Kitty: Christmas at Pemberley.” The modern play is an imaging of the holiday season within the lives of Jane Austen’s beloved characters, and how their family dynamic has continued to change past the happily ever after.
Mutts Gone Nuts: Santa Paws
Maybe you don’t consider yourself a traditional theater-goer; rest assured, there’s nothing typical about seeing a bunch of top-notch stunt dogs perform in a hallowed hall for Christmas. Mutts Gone Nuts tours with their highly-talented canine companions often, but their upcoming show at The Colonial Theater has a holiday twist. You just never know what’s going to pop up onstage around here!
Holiday Feasts & Treats
You just can’t get through a cold, dark winter without some good food. Luckily, we’ve got plenty of top-notch businesses to lend a helping hand with your holidays.
Christmas Eve To-Go at Mazzeo’s Ristorante
It’s a tradition in the Berkshires for many families to leave their Christmas Eve dinner to the professionals at Mazzeo’s. While their indoor table service is shut down for the holidays, you can place an order for single or family-style Italian meals to be picked up either hot or oven-ready on Christmas Eve. You just can’t go wrong with their excellent food and generous portions! But take note–since this holiday tradition is so popular, you have to place your order a few days ahead of time. You can even do this as a last-minute Thanksgiving plan!
Food events at The Barn Williamstown
The Barn is an upscale eatery located inside The Williams Inn. Though they haven’t yet released their specific menu for the Christmas season, they’ve been known to do delicious pre-fixed menus for Christmas Eve and Christmas Day with seasonally-inspired meals and drinks. You may also find Santa having brunch here in the days before Christmas! Like all other limited-supply holiday meals, be sure to make your reservation early if you plan on dining out this Christmas.
Chocolate Springs: The Essential Hot Chocolate Stop
It’s the moment you’ve been waiting for: my pick for the best hot chocolate in the Berkshires. Is there any surprise that Chocolate Springs does it better than anyone else? Their cafe spot in Lenox is the perfect place to take a date or a child to warm up after a chilly day in the snow–you can find hot, iced, and espresso-infused drinks to enjoy while you browse their beautiful hand-made creations.
Christmas & Hanukkah Treats at Robin’s Candy
Robin’s Candy in Great Barrington is full to the brim with any candy you may need for your stocking stuffers: their stock spans generations and countries to find that long-lost candy you’ve been craving. You can also pick up advent calendars, chocolate and electric menorahs, and kosher chocolate coins.
Winter Specialty Drinks at Dottie’s
Going to Dottie’s downtown is one of my favorite parts of living in Pittsfield, and the quality of their seasonal drinks puts Starbucks to shame. It’s a great place to take somebody that loves to post pictures of their latte art! Plus, the team at Dottie’s will occasionally offer baked good platters of breakfast treats that make for great host gifts at your next holiday party.
Haven Home for The Holidays https://havencafebakery.com/
Looking for a little help with your holiday feast? Lenox’s Haven Cafe is known for their delicious foods and catering services, and they really step it up for the holiday season. You can get gourmet sides for you table like specialty stuffings, gravy, roasted vegetables and potatoes, and some baked goods to finish it off. They’ve got plenty listed for Thanksgiving, and are bound to offer even more options as Christmas gets closer.
I hope this run-down helps you live your Berkshire winter to the fullest! If you’re looking for a new home to spend the holidays, I would be happy to speak with you–just go here. You can find more on the best parts of living western Massachusetts on my blog.
