Berkshires for the Holidays.

A Visit to the Berkshires

The Berkshire Mountain area of western Massachusetts is a prime getaway during the cooler months, starting with striking foliage and pumpkin festivals and continuing with sparkling Christmas lights and celebrations.

During the Gilded Age of the late 19th century, the area was known as a retreat for wealthy American tycoons and famous artists. 

Today, the quintessential small New England towns that comprise the Berkshires attract outdoor lovers and culture seekers, transforming into a winter wonderland when the snow begins.

While many of the Berkshires’ popular cultural institutions are closed due to Covid, there’s plenty to do to satisfy all ages. Be sure to pack your cold-weather gear and some sturdy walking shoes.

  • Cafe Boulud Blantyre desserts.
  • John Andrews Farmstand
  • Harvest Moon Restaurant.
  • John Andrews inside.

Dining in the Berkshires

The Berkshires’ acclaimed farm-to-table cuisine takes on a different cast during the holiday period, with restaurants emphasizing root vegetables, hearty proteins and holiday treats.

CafeADAM, Stockbridge

Modeled after a Berkshire country home, the upscale-yet-rustic CafeADAM is a welcoming space with an ever-changing menu of farm-to-table choices. During the holidays, seasonal inspirations find their way into cocktails as well as mains and appetizers. Crowd favorites like seared Cape Cod scallops and Korean BBQ pork ribs pair well with Vermont cider and local beer on tap.   

John Andrews Farmhouse Restaurant, South Egremont

In a setting marked by woods and landscaped gardens, John Andrews Farmhouse Restaurant is a Berkshires delight. The restaurant sits in a structure dating from the late 1700s on the original farmstead. An outdoor fire pit invites diners to enjoy a relaxing cocktail even in the coldest of temperatures.

The menu epitomizes the farm-to-table concept, with seasonal ingredients sourced from local farms and food artisans. Chef Dan Smith’s focus is one of taste-of-place dining, ensuring that you have a genuinely Berkshires experience with a menu built around regional producers of the moment.

Leave room for the sunshine kabocha squash pudding cake with ginger ice cream and maple butter, a worthy winter dessert created off the bounty of the season.

  • Seared Scallops at CafeADAM.
  • Canyon Ranch cuisine.
  • Cafe Boulud dinner at Blantyre.
  • Pumpkin Soup at Cafe Boulud Blantyre.

Old Inn on the Green, New Marlborough

Once a stagecoach relay station, the Old Inn on the Green hearkens back to New England’s past, using only candles and fireplaces to light its private dining rooms. Changing daily and determined by the day of the week, the Old Inn offers an a la carte or prix fixe menu along with a special Chef’s Tasting Menu. Reserve a table here for an evening of retro romance.

Café Boulud at Blantyre, Lenox

Michelin-starred Chef Daniel Boulud continues his successful residency at the luxurious Blantyre country manor. Using fresh and local ingredients, Boulud offers seasonal French classics with a New England twist.

The setting is Berkshires Gilded Age, with the Tudor-style Blantyre “cottage” decked out with proper holiday regalia and seasonal plantings, and the dining room as formal as you’ll ever find in the Berkshires.  Dress your best for one of the area’s finest dining experiences. On Thanksgiving, the restaurant’s three-course prix fixe dinner includes pumpkin soup with gruyère espuma and Berkshire turkey with shallot-rosemary gravy.

  • Naumkeag Winterlights.
  • Winter Lights at Naumkeag
  • Winter lanterns at Naumkeag.
  • Naumkeag Winter light trees

What to Do

There’s no shortage of activities to fill your days and nights in the fall and winter.

Find a hotel suited completely to your needs while staying in the Berkshires here. If escaping to a home away from home is more your style check out these homes available to book for a short stay here.

Winterlights at Naumkeag

An annual sellout, Winterlights is an illuminated wonderland of thousands of lights at Stockbridge’s Naumkeag, a 44-room Gilded Age “cottage” with stepped gardens. Trees covered with shimmering holiday lights of many colors and overhead balloons and other lit designs wow visitors of all ages. Timed tickets are required for the outdoor experience and must be purchased in advance.

Berkshire Scenic Railway-Hoosac Valley Service

Children will love the train ride between Adams and North Adams in the Berkshire Hills of western Hoosac Valley. From restored 100-year old coaches, families will explore the region’s rich railroad history in the hour-long excursion. Trains depart from Adams on weekends and reservations are required. 

  • Stockbridge carriage.
  • Stockbridge in the fall.
  • Naumkeag winterlights wishes.
  • Naumkeag interior

Hancock Shaker Village

Pittsfield’s living history museum is beautiful in the winter months. The twenty historic buildings and numerous walking trails offer a deep dive into the simplicity and quality of Shaker life from the 1780s to the mid-20th century. The collection introduces visitors to the farms, artisans and distinctive furniture and textiles of this religious sect. Seasonal events include:

Thanksgiving on the Farm – November 27 and 28

Enjoy a day of woodworking and blacksmithing demos, Shaker talks, a Turkey Walk & Talk (registration required), hikes and children’s activities like smashing pumpkins and feeding them to the farm’s hungry pigs. 

The Village’s Holiday Market on Saturdays from Thanksgiving through December 19 gives visitors a chance to buy goods including hand-knit mittens, distinctive jewelry, clothing, bath products and toys, all from regional artisans.

On Saturday, December 12, the annual Village Family Day invites visitors to decorate cookies and make ornaments. Artisan demos, a gingerbread contest, storytime with Santa (registration required), a visit with the animals in the barn, caroling and Shaker talks are scheduled throughout the day. 

The celebration continues on December 31 with the Hibernation Celebration and its artist demonstrations, workshops and talks; s’mores over the fire; and a kids’ countdown to the end of the year. A Tree of Hope encourages visitors to write a wish for 2021 and hang it on the tree. 

  • Festival of the Trees.
  • Inside the Mount.
  • The Mount library.
  • The Mount Edith.
  • The Mount in the winter.

Berkshire Museum’s Festival of Trees 2020: Legends of the Berkshires

Monday, November 30, 2020 through Sunday, January 3, 2021

Also, in Pittsfield, this year’s version of the annual festival invites visitors and locals to explore tales from the Berkshires. Dive into the history of the first recorded baseball game, learn about the famous figures from the area and investigate rumors of mysterious sightings with a collection of bright and colorful winter displays spread across the city and surrounding communities. 

The Mount, Lenox

Sign up online for a self-guided holiday house tour of The Mount, the home of author Edith Wharton, adorned with festive decorations provided by the Lenox Garden Club. The “cottage,” designed Edith Wharton herself and built in 1902, reflects Wharton’s theories about classic European architecture, adapted for an American landscape. Advance reservations are required to visit the Main House. Plan to spend some time exploring the beautiful grounds of the estate.

Special Saturday events include winter storytime on November 30, paper ornament making on December 7, and a holiday concert on December 21.

  • Galleries around Lenox.
  • Downtown Lenox.
  • Safety signs around Lenox.
  • Christmas lights.


The Mount’s newest holiday program is offered on Thursdays – Sundays from November 19 – January 3.

An evening event, NightWood is a sound and light experience that transforms the property into a fantastical winter landscape for the holidays. Inspired by the natural beauty and architecture of The Mount, NightWood immerses visitors in a series of vignettes designed to evoke elements of fantasy, tradition and whimsy. Advance timed tickets are required.

Ventfort Hall and The Museum of the Gilded Age, Lenox  

Arrange to tour another Gilded Age mansion, Ventfort Hall, an imposing Jacobean Revival-style mansion built in 1893 for Sarah Morgan, the sister of J. P. Morgan.  The Museum of the Gilded Age interprets the great changes in American life, industry and society during the nineteenth century. Reservations required for self-guided tours.

MASS MoCA, North Adams

Recently portrayed in the documentary Museum Town, MASS MoCA is a distinctive setting for evocative art. In a sprawling complex of former 19th-century mill buildings, the art center has vast galleries, performing arts venues and both permanent and purpose-built exhibits by innovative artists. An elaborate system of interlocking courtyards and passageways connect the 26 buildings. Saved from more than a decade of disuse in a Herculean effort to revive the town’s lagging economy, the complex was previously a textile factory and, most recently the home of the Sprague electric company.

  • Mass MOCA
  • Mass MOCA interior
  • Exhibit in Mass MoCA.
  • Aerial view of Mass MoCA.
  • Modern exhibit at MoCA.

Norman Rockwell Museum, Stockbridge

With its nostalgic depictions of life through illustration by Berkshires resident Norman Rockwell, the Norman Rockwell Museum offers an enjoyable visit for all ages. Adults will appreciate the social commentary as espoused in Rockwell’s art. The current Imagining Freedom exhibit is especially relevant today and explores the fundamental human freedoms of speech and worship and freedom from want and fear. The exhibition hosts Rockwell’s Four Freedoms, along with works from artists working for the cause of freedom. The most popular cultural attraction in the Berkshires, the museum requires advance purchase of timed tickets.

Clark Art Institute, Williamstown

One of the country’s most acclaimed small museums and a pioneer in children’s programming, The Clark Art Institute offers indoor art exhibits as well as outdoor installations. The museum is noted for its collections of Impressionist, American and other art. Book timed tickets online with admission free on the First Sunday of the month.

A unique musical event on December 5 and a Start with Art day for preschoolers with a take-home art-making kit on December 12 are scheduled for holiday vacation time. 

The museum takes advantage of its 140 acres, offering Project Snowshoe for outdoor art exploration and trail walks. Grab a pair of snowshoes from the snowshoe hut (multiple sizes available) and experience the outdoor exhibition Ground/Work

  • Pleasant Valley hike.
  • Pleasant Valley hike.
  • Clark Museum Piano hall.
  • In galleries at Clark museum.

Hiking in the Berkshires

For more hiking and snowshoeing, the following resources can be guides to trails in the Berkshires:

Laurel Hill Association – Stockbridge

Pleasant Valley – Lenox

Download this app for complete information 

Be prepared for every trail with a pair of lightweight hiking boots and layers from Colombia here.

  • Pathway in the snow at canyon ranch lenox wellness center.
  • Canyon Ranch snowy mansion.
  • Miraval Berkshires nature
  • Bellefontaine Mansio at Canyon Ranch Wellness Center.
  • Miraval entrance.

Where to Stay

Wellness is a key watchword in the Berkshires, no matter what season. During the holiday months, you can retrench with fitness and spa activities both indoors and outdoors.

Canyon Ranch Lenox

Canyon Ranch offers life-enhancing “pathways,” curated wellness programs of varying lengths to help visitors rejuvenate and de-stress. During the winter, gingerbread houses decorate the Bellefontaine Mansion and special dance weekends add a fun way to keep you moving. For Chanukah, the Ranch will hold a nightly menorah lighting. If the weather cooperates, the Ranch’s beautiful grounds are the perfect place for cross-country skiing and snowshoeing. Indoor squash, tennis, racquetball and basketball courts complement the daily fitness classes and holistic spa treatments.

Miraval in the Berkshires, Lenox

Newly opened in the Berkshires, Miraval is known for its fitness and wellness focus. Activities including aerial yoga, horse whispering, hiking, biking, stargazing and snowshoeing make for a diverse and indulgent experience at the expansive property. Spa programming is an integral part of the Miraval journey, combined with a culinary emphasis on balance. For an evening to remember, Miraval invites guests to book a private dining session in the Life in Balance Culinary Kitchen.

  • Red Lion Inn is open.
  • Wintery Red Lion Inn.
  • Red Lion Inn singers
  • Red Lion Inn Tavern.
  • Red Lion Inn center stairs
  • Red Lion Inn dining room.

Red Lion Inn, Stockbridge

When the cold weather hits, the historic Red Lion Inn looks like it stepped out of Norman Rockwell’s painting of Main Street in Stockbridge, Home for Christmas. One of only a few American inns operating continuously since before 1800, The Red Lion appeals to Americana buffs with its decorated Rockwell-esque front porch and holiday carolers regaling guests on the steps. Indoors, live Christmas trees, Christmas kissing balls, poinsettias, yards of garland and handmade wreaths on every guestroom door create the holiday mood. For much of December, pianists and harpists play holiday favorites in the lobby. 

Wheatleigh, Lenox

On 22 acres overlooking the Berkshire Mountains and lake, five-star Wheatleigh is a Berkshires treasure. Built in 1893, the 19-room Italianate mansion offers privacy and seclusion. Wheatleigh caters to a refined clientele with a museum-like setting with antiques, architect-designed furnishings and original contemporary art. Dining during the holiday period is limited to overnight guests, and a full “palazzo” buyout can be had for up to 25 people. 

  • Devonfield Inn in the winter.
  • Blantyre Patterson Suite. Photo by Blantyre
  • Sculpture on fall grounds at Blantyre. Photo by Blantyre
  • The lush Blantyre grounds.
  • Cafe Boulud at Blantyre.

Blantyre, Lenox

The Gilded Age is alive and well at Blantyre in Lenox. A Tudor-style mansion and estate built in 1902, Blantyre is a member of the elite Relais & Châteaux consortium. In an oft-photographed setting, the luxury resort features a range of elegant guest accommodations, a spa and Daniel Boulud’s legendary French cuisine. A must-see, the baronial Main Hall is a showcase of period pieces, heirlooms and art. Guests are welcome to explore Blantyre’s 100 acres of lawns and woodlands or snowshoe the resort’s trails that hug the perimeter. Other seasonal activities can be arranged by the concierge, with an on-property Christmas tree lighting one of the most popular events.

Devonfield Inn, Lee

An English-Style country house originally built in the early 1800s, Devonfield Inn overlooks a meadow shaded by birch trees against a backdrop of rolling hills. Indoor and outdoor holiday decorations set the tone for the festive period at the B&B. Popular activities are cross-country skiing on Devonfield’s extensive grounds and a program for winter horse riding with HorseWorks Farm. Thanksgiving dinner is offered for guests. Charm and coziness radiate throughout, with the inn’s owners adding thoughtful touches like a stocked guest pantry and complimentary cognac and cordials.

Meryl Pearlstein

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