Recently, I asked a friend who grew up in the Berkshires how his family had spent their winters in the mountainous region. He answered with an adamant “Inside!” What a shame, I thought. Most people who’ve been to this western corner of Massachusetts experience it in summer—when stalwart and novice pilgrims alike cram their calendars with world-class performing and visual arts. But snowfall and cold weather hide few of the Berkshires’ charms. Quite the opposite, in fact: Winter reveals many more.
This is where to trade splashing through city slush for snowshoeing in woods shared by overwintering moose, bobcats and foxes. Many of the cultural institutions don’t hibernate either; the recently, splendidly restored Mahaiwe Performing Arts Center presents a busy winter schedule of filmed performances of plays by London’s National Theatre; classic movies; and concerts by musicians on a spectrum from Yo-Yo Ma to Diana Ross.
A little shopping for antiques or contemporary goods, or the appeal of a massage at a mansion-housed spa, pulls some skiers and snowboarders down from the Berkshire Mountains’ approximately 1,000 skiable acres. And come dinnertime, you’ll find wine and craft-beer bars and locally sourced fare at cozy restaurants—where there’s a good chance of finding barstools and tables by a roaring fire.
Schussing Into Winter
Berkshire towns are about 10 to 20 minutes apart by car. Hurrying is discouraged here. Driving on two-lane roads and “highways,” whose speed limits hover no higher than 50 mph, is worth it to see the snow-fluffed fields and villages—straight from a Grandma Moses painting—you’ll pass along the way.
Wherever you’re staying, downhill skiing for all ages is not too far away. Jiminy Peak, 12 miles from Pittsfield, is the biggest ski center in a collection of small to medium ones. (Compare Jiminy’s 45 runs and 1,150-foot drop to, say, the 127 runs and 4,425-foot drop at Colorado’s Telluride.) The smaller Bousquet Mountain, just south of town, is more sparsely attended and less expensive than most of its peers, part of the reason the passionately opinionated Skibum.net ranks it the best in the Berkshires. Ski Butternut, east of Great Barrington, suits the “relaxed” skier and has especially kid-friendly slopes.
Taking It Easier
Those preferring a more meditative pace can head to the Arcadian Shop in Lenox to rent cross-country skis or snowshoes. The store suggests customers use its webby footwear on Lenox’s 500-acre Kennedy Park, set right behind the store and polka-dotted with walkers, skiers and sledders. After a frosty workout, you can warm up with hot drinks at the in-store Trailside Café.
A less populated swath of the silent white landscape, Hollow Fields’ 40 acres are protected by the Berkshire Natural Resources Council. BNRC’s occasional guided tours lead participants above the gorgeous sea of snow to look for signs of winter wildlife. Otherwise, a trail map helps you find your own way.
Museums and Performing Arts
Any Berkshire sojourner who skips Mass MoCA’s enormous North Adams campus—it’s the largest contemporary art museum in the country—will practically be committing a cultural crime, especially since the completion of the latest galleries, in Building Six. Along with installations by artists including Laurie Anderson and Jenny Holzer, the space houses the late Gunnar Schonbeck’s handmade instruments of his own invention and appeals to even nonmusical visitors. At The Mount, Edith Wharton’s former Lenox residence, the famous garden is dormant in winter, but the house regularly hosts literary events related to both Wharton’s work and others’. Tours of the interior can be made by appointment at this time of year. In Stockbridge, the Norman Rockwell Museum celebrates the master American illustrator’s trenchant, loving depictions of American life while also championing the work of other artists. A holiday exhibit stays up through February 2018, and “Never Abandon Imagination,” featuring American fantasy artist Tony DiTerlizzi—who cites Rockwell as an influence on a timeline between Hieronymus Bosch and Jim Henson—runs through May 2018. For HD-streamed performances by the Metropolitan Opera and the Bolshoi Ballet, movies and more, check out the schedule at Great Barrington’s Mahaiwe Performing Arts Center, a landmark since 1905.
Getting House Proud
The Berkshires’ range of unusual, beautiful and useful wares for any room in the house is mind-expanding. At One Mercantile, in Great Barrington, you’ll find ceiling lamps with long cords in an array of colors, red metal first-aid kits worth putting on display, and rustic-chic rugs made of flattened firehoses. A short walk north leads to Farm & Home, which has shelves lined with contemporary pottery. Here, large Depression-era reach-in coolers still bear their original signage—“Please serve yourself”—but are filled with tidy rows of notebooks and many-shaped soaps (one in the form of an avocado). In the back of the store, you might run into co-owner Chapin Fish, who practices real estate at a desk in the midst of everything. In Lenox, Design Menagerie promises “Objects of Utility and Beauty” and keeps its word. Women’s unusual, minimalist, un-retail-looking accessories is Rei Kawakubo–meets–Eileen Fisher; and quilts by artisan Louise Gray are flexibly designed to use on a bed or hang on a wall.
Taking the Edge Off
After a day of skiing or walking from shop to shop, think about heading to one of two mansions turned resorts for a massage or other soothing services. In Lenox, both The Potting Shed Spa at Blantyre and The Spa at Cranwell are open to nonguests—but even in colder months it’s wise to make an appointment in advance.
West Stockbridge has an artsy-craftsy Main Street, but if you’re not in the mood, consider giving this town its due at three cheek-by-jowl establishments of a different kind. All day at the busy No. Six Depot, the clientele lines up patiently for coffee hand-roasted on-site and takes fresh pastries, salads and paninis to tables beneath a rotating display of sophisticated works by local and international artists. The café also hosts pop-up dinners prepared by up-and-coming New England chefs. Across the street, Shaker Mill Books houses an abundance of new, used and rare books, as well as those by local authors; owner Eric Wilska is restoring a nearby barn to house even more inventory. Down the street, Charles H. Baldwin & Sons makes vanilla extract and other goodies, such as Mr. Baldwin’s Proper Bloody Mary Mix and maple syrup, which are tempting enough to make adults feel like kids in a candy store (meanwhile, loads of real candy keep real kids happy too). It was the Mohicans who taught the first settlers here to tap maple trees and boil the sap down to syrup—just one bit of magic from experiencing the Berkshires in winter.
101 Dan Fox Dr., Pittsfield; 413-442-8316; bousquets.com
Visit website for detailed directions
37 Corey Rd., Hancock; 413-738-5500; jiminypeak.com
Behind the Arcadian Shop, see “Shop”
380 State Rd., Great Barrington; 413-528-2000; skibutternut.com
Mahaiwe Performing Arts Center
14 Castle St., Great Barrington; 413-528-0100; mahaiwe.com
1040 Mass MoCA Way, North Adams; 413-662-2111; massmoca.org
2 Plunkett St., Lenox; 413-551-5111; call ahead to inquire about winter operating hours; edithwharton.org
Norman Rockwell Museum
9 Glendale Rd., Stockbridge; 413-298-4100; nrm.org
10×10 Upstreet Arts Festival
The annual winter arts festival hosted by Barrington Stage Co. and Pittsfield’s Office of Cultural Development hosts 10 days of dozens of events, including fireworks, a wildly popular 10-minute-play festival, art auction, poetry slam and dance performances. Feb. 15–25, 2018, at various venues, Pittsfield; 413-499-9348; discoverpittsfield.com
91 Pittsfield Rd., Lenox; 413-637-3010; arcadian.com
Charles H. Baldwin & Sons
1 Center St., West Stockbridge; 413-232-7785; baldwinextracts.com
26 Housatonic St., Lenox; 413-551-7528; designmenagerie.com
Farm & Home
276 Main St., Great Barrington; 413-528-9100; farmandhome.us
8 Castle St., Great Barrington; 413-528-1718; one-mercantile.myshopify.com
Shaker Mill Books
3 Depot St., West Stockbridge; 413-232-0251; shakermillbooks.com
The Potting Shed Spa at Blantyre
16 Blantyre Rd., Lenox; 844-881-0104; blantyre.com; spa services, from $125
The Spa at Cranwell
55 Lee Rd., Lenox; 413-637-1364; cranwell.com; massages, from $60
Freight Yard Pub and Restaurant
A good stop for its broad-ranging menu—think soup to nuts (or omelets to steaks)—near Mass MoCA. 1 Furnace St., North Adams; 413-663-6547; thefreightyardpub.com; dinner for two, $60*
Mission Bar + Tapas
On Thursday nights a local music collective plays at this classic neighborhood haunt with American “tapas,” like mac ’n’ cheese. 438 North St., Pittsfield; 413-499-1736; missionbarandtapas.com; dinner for two, $30
No. Six Depot
6 Depot St., West Stockbridge; 413-232-0205; sixdepot.com; lunch for two, $25
A small, airy storefront restaurant that collaborates with local farmers and craft-food makers to realize a creative yet comforting menu. 37 Church St., Lenox; 413-551-7183; nudelrestaurant.com; dinner for two, $100
The Old Inn on the Green
High-style local fare, such as Hudson Valley foie gras, served in rooms lit entirely by candle- and firelight. 134 Hartsville–New Marlborough Rd., New Marlborough; 413-229-7924; oldinn.com; dinner for two nonguests, $70
Rubi’s Coffee and Sandwiches
In a sunny space at the end of an alley off Main Street, with espresso, fresh pastries, sandwiches and an enormous fireplace. 264 Main St., Great Barrington; 413-528-0488; rubiners.com; lunch for two, $25
Widow Bingham’s Tavern
Dine on the likes of turkey sandwiches and Lion’s Ale beer-battered haddock in a bar connected to the oldest hotel in Stockbridge. The Red Lion Inn, 30 Main St., Stockbridge; 413-298-5545; redlioninn.com; dinner for two, $50
RCI® affiliated resorts in the Berkshires include:
All of the cushy accommodations feature a kitchen and a hot tub. 276 Brodie Mountain Rd., Hancock
Member Review: “Serene and quiet setting.”
Equipped with an indoor pool and lots of other on-site activities for families. 190 Meadow St., South Lee
Member Review: “Fantastic location.”
When you’re not out and about, you’ll appreciate the resort’s modern amenities and plush living and dining areas. 8 Dan Fox Dr., Pittsfield
Member Review: “Lots of hiking trails nearby and great scenery.”
Access to outdoor activities, shopping and great restaurants makes this an idyllic Berkshire getaway. 949 S. Main St., Great Barrington
Member Review: “The rooms were excellent.”
At the base of Jiminy Peak, this resort offers a reprieve after full days visiting the nearby attractions. 1 Corey Rd., Hancock
Member Review: “Nice pool and waitstaff.”
For complete member reviews (as member reviews have been condensed) and additional resort listings, visit RCI.com or call 800-338-7777 (Weeks) or 877-968-7476 (Points). Club Members, please call your specific Club or RCI telephone number.
Non-RCI affiliated resorts in the Berkshires include:
The Briarcliff Motel
A retro ’60s-style motel conveniently located at Monument Mountain. 506 Stockbridge Rd., Great Barrington; 413-528-3000; thebriarcliffmotel.com; doubles from $90 a night
Hotel on North
No two rooms are alike at this boutique property. 297 North St., Pittsfield; 413-358-4741; hotelonnorth.com; doubles from $159 a night
The Red Lion Inn
Guests can choose between the main inn and private guest houses, many named for former residents. 30 Main St., Stockbridge; 413-298-5545; redlioninn.com; doubles from $114 a night
The Old Inn on the Green
This historic inn—a former stagecoach relay—has candlelit dining rooms and pastoral murals. 134 Hartsville–New Marlborough Rd., New Marlborough; 413-229-7924l; oldinn.com; doubles from $260 a night (including breakfast and one overnight dinner)
- *Estimated meal prices do not include drinks, tax, or tip.
- NOTE: Information may have changed since publication. Please confirm key details before planning your trip.
- Published: Winter 2017