Snow Much Fun! Your Guide to a Winter Getaway in the Berkshires

Winter is a time for celebration, something that’s especially true if you make time for a seasonal trip to the stunning Berkshires. While other spots get bogged down in slushy streets and grey skies, the small towns that help make New England so special not only stay alive, they burst into colorful life. From twinkly lights hung with care to museums and performance venues that bump up their show schedules and exhibits to reflect the merriment of the holiday season, there is so much to do in the Berkshires during winter, not in spite of the cold but because of it.

Outdoor Adventures

Outdoor exploits are everything in the Berkshires, even when winter hits – or maybe especially in winter. Cold weather brings big snows, stunning landscapes, and more opportunities to ski, snowshoe, hike, ice skate, and so much more.

Most parks, including the Berkshire East Ski Area, are equipped for a variety of winter fun. Visitors can ski, snowboard, or try their hand at tubing across 45 trails, some lit for nighttime exploration. The 22 kilometers of groomed track trails at Canterbury Farm are dedicated to cross-country skiing, though skating and snowshoeing are also on offer; work up an appetite, then head to the den for hot chocolate and a chance to catch your breath. Eager for something a bit faster paced? Check out snowmobiling. The Berkshire Snow Seekers Snowmobile Club monitors trail conditions and may be able to help newbies find a ride.

Most of the year, Hilltop Orchards is known as a pastoral oasis offering wine tastings and full moon hikes, but in winter the hiking trails turn into cross-country ski tracks. Hilltop rents out skis and snowshoes and offers PSIA-certified instruction for those just starting out, and there’s a special guided full moon snowshoe trek and bonfire for an extra special night out.

For those who would rather watch the action than take part, there is the Bay State Winter Games. The organization is still finalizing the dates for 2019, but spectators can expect a fun-filled event featuring athletes aged 5 to 70 (and sometimes beyond). Competitors come from across New England for events in alpine skiing, cross-country skiing, curling, ISI figure skating, USFS figure skating, and ice hockey.

Cozy Dining Options and Belly-Warming Cocktails

When the hills are alive with a continual onslaught of snow flurries, stay warm with a bite to eat at one of the Berkshire restaurants boasting a working fireplace. The Old Mill incorporates all kinds of naturally warm elements, including wrought-iron sconces and the aforementioned wood-burning forge, and the Onion Soup Gratinee is the best of its kind in Western Massachusetts. At Firefly Gastropub & Catering Co., you can enjoy a signature grilled Caesar salad or small bites like avocado smoked salmon toast as the firelight dances off your dining companion’s silverware.

For warm drinks on a cold day, head to No. Six Depot Roastery & Café. Part coffeeshop, part tea house, part art gallery, this spot in West Stockbridge combines small-batch beverages with a menu filled with tasty options like a breakfast burrito with queso fresco or a vegan panini stuffed with locally made tempeh, Crimson kraut, arugula, and a basil-orange vinaigrette. Fuel in Great Barrington is a nice place to relax with a latte and your laptop if you’re working during your Berkshires escape while the Chocolate Springs Café delivers luscious hot chocolate, live music, and a convivial atmosphere – plus gelato if you don’t mind a chilly snack on an equally chilly day.

Can’t pick just one spot to satisfy your appetite? Treat your taste buds to a range of flavors during Restaurant Week, also known as North County Eats. The details for the 2018 version of the foodie fest were still under wraps as of this writing, but the event typically takes place at the end of January into the first week of February.

Museums, Art and Culture

Baby, it’s cold outside! So why not ditch the soggy scarf and snow boots and head indoors for some cultural experiences?

There are a number of museums in the Berkshires, but the Massachusetts Museum of Contemporary Art is one of the best. MASS MoCA, as it’s often called, is situated in a restored 19th-century factory, itself an architectural masterpiece, and inside you’ll find a wide range of exhibits that run the gamut from thought-provoking paintings and sculpture to cutting-edge performances. Art is also the theme at The Clark, but rather than modern exhibits there’s a wealth of art and architecture focused on the work of the old masters from the Americas, Great Britain, and Europe.

Herman Melville’s Arrowhead is a literary enthusiast’s dream. The farmhouse, now a historic landmark on the national registry, is where Melville wrote his most famous work – that’s Moby Dick, by the by – and there are guided tours and nature trails to traipse about if weather permits. Another historic spot is the Susan B. Anthony Birthplace Museum in Adams, Massachusetts. The famous and daring social reformer and abolitionist was born in this house-turned-historic-artifact, and now the building is preserved as a tribute to Anthony’s enduring legacy. Visitor can see textiles and furnishings from Anthony’s lifetime as well as other bits of memorabilia and there are frequently special events that shine a light on issues in line with the museum’s mission.

Baseball season wraps up with the World Series in October, but in the Baseball in the Berkshires is a year-round event. Some 40 major league players have close ties to the Berkshires, so it makes sense that a museum dedicated to baseball history would find its home in Lanesborough.

There are several wonderful theaters in the Berkshires, including Shakespeare & Company, a theater group dedicated to the work of the Bard himself. The theater also offers the Winter Studio Festival of Plays from January 19-20; in 2019, the festival features five reading focused on socially relevant topics followed by talk sessions with the actors and director. At the Berkshire Theatre Group, presentations are more thematically diverse; shows include plays, comedy events, musical tributes, and art displays, all of which serve as a welcome respite when winter winds scuttle your plans for a snowy hike or snowmobile ride.

Schedule your trip to the Berkshires in mid-to-late February and your visit will coincide with the 10×10 Upstreet Arts Festival in Downtown Pittsfield. Tons of local organizations and institutions ranging from the Berkshire Music School to Hancock Shaker Village to the Barrington Stage Company come together to celebrate the arts with showcases, workshops, and free community get-togethers.

Wintering in the Berkshires with the Wee Ones

Cabin fever is bad enough in adults, but even the most well-appointed luxury lakeside cottages can’t contain active children indefinitely. Before everybody loses their minds, take the family somewhere they can lose their inhibitions and let their imaginations run free.

First stop? The Eric Carle Museum of Picture Book Art. Carle’s books are iconic – almost every kid has a copy of The Very Hungry Caterpillar or Brown Bear, Brown Bear – and those books are complemented by artwork from other favorites such as Where the Wild Things Are and Why Mosquitos Buzz in People’s Ears. Visit the Carle Museum as a standalone trip, or grab a combined ticket for the Iconic Illustrators Trail and hit up the Norman Rockwell Museum in Stockbridge and The Springfield Museums, home to the Amazing World of Dr. Seuss, for one affordable price.

A Happy Holiday – and Jolly New Year – in the Berkshires

Once November hits, the Berkshires spring to life with a flurry of holiday-themed activities and events. The Festival of Trees runs for nearly two months, giving locals and tourists alike plenty of time to soak up the sap-tinged whimsy that is dozens of holiday trees decorated to reflect the artist’s chosen theme. From the weird to the nostalgic, garden parties to toy explosions, the display is a veritable wonderland of art and imagination.

Downtown Lenox comes alive with light during the city’s Making Spirits Bright event. It’s a weekend of holiday magic, with a classic tree lighting ceremony, light night shopping parties, a restaurant crawl complete with Old Saint Nick himself, public performances, and so much more. If you’re in town the weekend of December 7, 8, and 9, try and make time for the holiday tours on Saturday and Sunday – it’s breathtaking and exciting to see venues like the Birchwood Inn, Church on the Hill, and Ventfort Gilded Age Mansion decorated for the season and open to the public.

For holiday shopping, forget dime-a-dozen gifts from those mega online retailers and spoil your loved ones with special finds sourced from the Sheffield Historical Society’s Festival of Holidays at the Old Stone Store. The pop-up bazaar, which is in its 18th year, runs on weekends from early November through Christmas Eve and features all kinds of family-friendly items made by local artisans.

Train enthusiasts of all ages will love a ride on the Tinseliner, a throwback adventure courtesy of a 1950’s choo choo and the Berkshire Scenic Railway Museum. Passengers are treated to hot cocoa and have a chance to roast marshmallows, plus there’s a quick stop at the PopCares Tree Lot where interested parties can purchase a tree to pick up later on (proceeds from the lot benefit a Williamstown-based organization that supports cancer patients). The Railway Museum also hosts Mistletoe & Martini, a cabaret experience that combine strain travel and holiday music from Berkshire favorites Sam & Ron.

Traditionalists should book their tickets early for the Berkshire Theatre Group’s run of Dickens’ A Christmas Carol. There are only a dozen or so performances planned, including three matinees, plus a sensory-friendly performance in mid-December. Prepare for your evening of throwback entertainment with a morning or afternoon visit to Ventford Hall Mansion’s Home for the Holiday program. The grounds and interior of the gilded age property are decked out in holiday finery and there are guided tours almost every day for the duration of the season (actual holidays excluded).

Anchor your winter trip to the Berkshires with a stay in waterfront luxury at The Lake House. Enjoy a warm retreat nestled next to your own stone-decked gas fireplace or seek out hidden spots on the property courtesy of a cross-country ski or snowshoe excursion. Check out our cottages to see which of our spectacular accommodation options is right for you, or call us at (413) 446-0017 for more information or to secure your booking today.