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berkshires guide

by Stephanie

Illustration by Julia Rothman

Today’s Berkshires  guide comes from Frances Duncan, a web designer and local foods advocate who migrated to the Berkshires after a lifetime in and around New York City. Frances offers a glimpse into this outdoor haven with a comprehensive list of must-see-and-do items! Thanks, Frances, for sharing the wonders of the Berkshires with us! — Stephanie

CLICK HERE for the full guide after the jump!

Berkshire County Guide

Berkshire County — better known simply as “the Berkshires” — is a long strip of land along the western border of Massachusetts bordered by Vermont, New York and Connecticut, and adorned by the soft, rolling peaks of the Appalachian range. I migrated from Manhattan to the Berkshires in the summer of 2007. It’s been an adjustment — the pace of life here is slower and quieter than anything I was used to, but there’s something quite magical about living in a gorgeous vacationland 24/7. It’s also exciting to be part of the arts resurgence happening in the sleepy, formerly industrial mill towns that punctuate the landscape here.

This region is beautiful. Rivers wind their way through the hills and valleys, and the land is dotted with with silvery lakes, imposing rock formations and trees, trees, trees. In summer, the countryside is all green hillsides, wildflower meadows and productive farmland — it’s not uncommon to see cows wandering through stream beds while puffy clouds float overhead. Autumn, on the other hand, brings a riot of color as the trees transform from green to yellow, orange, red and brown, and apples and pumpkins are brought in from the fields. Along with its spectacular pastoral beauty, the Berkshires have long been known as a cultural destination. Now, longtime arts and culture heavyweights like Tanglewood and MASS MoCA are being joined by an explosion of smaller galleries, and the shops and services that come along with them. Meanwhile, the food scene plays to the area’s strengths — farm-fresh produce, artisanal cheeses and pasture-raised meats. Farmers’ markets from tiny to huge take over parking lots and fields on weekend mornings.

Though the bulk of tourism occurs in the summer, autumn is a beautiful time to visit, as the trees change color and the humidity vanishes. Even winter brings small-town skiing and silent snowshoeing. (Spring, however, is just a muddy mess.) Here are some of the hidden and not-so-hidden gems of my adopted home — a biased take on a small slice of a very pretty place.

The Lay of the Land

The county can be divided roughly in half, south and north, with the small, arts-centric city of Pittsfield in the center. South County is home to the venerable Tanglewood, and is what people likely think of when they conjure up an image of the Berkshires, while North County’s burgeoning underground arts scene has started making some waves — see September’s piece in the Financial Times about Pittsfield as the “Brooklyn of the Berkshires.”

South County

Southern Berkshire county begins in Lenox and stretches all the way down to the Connecticut border. Down here, upper-crust country summer homes abound: huge mansions and towering estates — some historically relevant and open to the public — peek out from expansive lawns. The action in South County occurs mostly in Lenox and Great Barrington, a bustling little New England town jam-packed with shops and eateries, nearly all of which are worth at least a peek. A trip to GB — as the locals call it — will keep you busy for the better part of a day, or use the town as a jumping-off point for more southern Berkshire county adventures.

Places to Stay

Stonover Farm This farmhouse, cottage and schoolhouse offers super-luxurious B&B accommodations on lovely grounds, complete with hay barn and duck pond. 169 Under Mountain Rd, Lenox, MA; 413-637-9100

Red Lion Inn This 18th-century inn is straight out of a Norman Rockwell painting — literally — and the country-chic rooms are appointed with all the amenities you’d expect in a luxe hotel. The wrap-around porch is a New England classic. 30 Main St, Stockbridge, MA; 413-298-4495

Inn at Sweet Water Farm Tucked away in a quiet corner of Great Barrington, the Inn at Sweet Water Farm had me at “line-dried cotton sheets and glowing pre-revolutionary hardwood floors.” 1 Prospect Lake Road, Great Barrington, MA; 413-528-2882

Race Brook Lodge The lodge, also equipped with a carriage house and cottages, calls itself a “chintz-free rustic mountain hideway” and is located squarely in the path of some of the best hiking in the county. Bonus: it’s affordable in a land of pricey luxury digs. 864 South Undermountain Rd. (Rt 41), Sheffield, MA; 1-888-RBLodge

Places to Eat, Drink and Snack

Chocolate Springs Handmade chocolate confections, hot and cold. Try the dark chocolate caramel with sea salt — grab an espresso while you’re at it — and be prepared to take some home with you. 55 Pittsfield Lenox Rd; Lenox, MA 01240; 413-637-9820

Nudel Inventive, ambitious seasonal food with a focus on pasta and an ever-changing menu. Sit at the bar and chat with the chef as he works his magic. 37 Church Street, Lenox, MA 01240; 413-551-7183

Lenox Coffee Purveyors of Barrington Coffee Roasting Company coffees and espresso, you can get a very good cup at this tucked-away spot. Free WiFi, too. 52 Main St, Lenox, MA 01240; 413-637-1606

Chez Nous A sweet French bistro run by a husband-and-wife team, serving delicious classics. 150 Main St, Lee, MA; 413-243-6397

The Dream-Away Lodge This legendary restaurant, that some say was once a brothel, is in the middle of nowhere, and that’s really saying something for a place with a lot of nowhere to be had. The food is simple, the drinks are stiff, the entertainment is local and the fire pit is roaring. 1342 County Rd; Becket, MA; 413-623-8725

Red Lion Inn Not only can you stay at this classic inn, but you can also eat here. On Sundays and Mondays the kitchen features a sustainable menu, highlighting locally grown and produced ingredients. 30 Main St, Stockbridge, MA; 413-298-4495

Moe’s Tavern The “No Coors Light” sign should tip you off — this is a place for serious microbrew-quaffing, hop-varietal-discussing, ale-and-food-pairing beer lovers. 10 Railroad St, Lee, MA; 413-243-MOES

Gypsy Joynt This friendly spot tucked away in a strip mall has a bit of a hippie, lentil-loaf vibe, but the food is homey and unpretentious. 389 Stockbridge Rd, Great Barrington; 413-644-8811

Baba Louie’s Pizza! This stuff is organic, wood-fired sourdough, and a bit of a regional institution, with a new location in Pittsfield, too. 286 Main St, Great Barrington, MA; 413-528-8100

Rubiner’s Cheesemongers This fromagerie, housed in an old bank, is like a temple to cheese, and you might feel like thanking your preferred deity when you arrive. Upon entering, a fresh array of cheeses — some under glass domes, some atop stately slabs of marble — await your tasting pleasure. Sample everything, making sure to heed proprietor Matthew Rubiner’s expert suggestions — this guy knows his stuff — and purchase as much as you can cram into a cooler to bring home with you. 264 Main St, Great Barrington, MA; 413-528-0488

Rubi’s Tucked behind Rubiner’s, and a must-visit in its own right, is Rubi’s. Yes, panini have had their time in the sun, but the panini at Rubi’s — to say nothing of the expertly pulled espresso — is more than worth waiting in line for. Secure a spot at the big wooden table in the back, and peruse someone’s abandoned New York Times over a latte while you wait for your sandwich to finish up on the grill. Do not miss. 264 Main St (rear), Great Barrington, MA; 413-528-0488

SoCo Creamery Homemade, small-batch ice creamery. Need I say more? 5 Railroad St, Great Barrington, MA; 413-528-9420

Allium Restaurant + Bar Each item on the menu at Allium comes with a pedigree because the ingredients are sourced with pride from the fields and farms of Berkshire county. On a warm day, you can check out the Great Barrington street life through the open garage-door-style window at the front of the space. The bar is open late, so stop in for a nightcap. 42 Railroad St, Great Barrington, MA; 413-528-2118

Route 7 Grill Farm-to-table American BBQ and comfort food in a casual and friendly setting. Personally, I couldn’t get enough of the mac and cheese. 999 Main St, Great Barrington, MA; 413-528-3235

Stagecoach Tavern A cozy, wood-beamed tavern serving sophisticated contemporary American food with a locavore bent. 864 S. Under Mountain Road, Sheffield, MA; 413-229-8585

Places to Shop

Pine Cone Hill Vibrant, vintage-inspired textiles for the home. 333 Pittsfield Rd, Lenox,MA; 413-637-1996

Evviva Unique clothing, jewelry and accessories, mostly by American designers. 22 Walker St, Lenox, MA; 413-637-9875

C. Baldwin Extracts Stock up on vanilla and other handmade baking and cooking extracts at this throwback of a store, originally established in 1888. 1 Center Street; West Stockbridge, MA; 413-232-7785

The Bookstore Last time I was here, the easy-going owner waited patiently for me to page through a few selections before informing me that the store was, in fact, closed. Oops. One of a dying breed, this independent bookstore stocks new and used books and encourages lazy browsing. 11 Housatonic St Lenox, MA; 413-637-3390

Seeds Super-cute little gift store stocked with contemporary, modish design objects, calendars, jewelry and small home accessories. 34 Railroad St, Great Barrington, MA; 413-528-8122

Hammertown Home furnishings and accessories with a “modern country” sensibility. 325 Stockbridge Rd, Great Barrington, MA; 413-528-7766

Germain If you’re anything like me, you will immediately want to move in to this rustic-industrial-chic space, which sells contemporary and vintage home goods, plus understated, urbane clothes. 635 Main Street, Great Barrington, MA; 413-644-8868

Things to See and Do

Tanglewood It’s a summer institution — grab a blanket, stock up on picnic provisions and wine from Guido’s and secure yourself a lawn ticket for a performance at Tanglewood. All summer long, the Boston Symphony Orchestra plays classical tunes alfresco while you sit back and enjoy the fresh country air. Classical music not your thing? (Does it matter? You’re picnicking!) Go for film night, featuring classic scores and soundtracks, instead. West St off Rte 183, Lenox, MA; 413-637-5165

Kripalu What’s a get-away without a little rest and rejuvenation? Stop by for a workshop at Kripalu, where you can get bendy in a yoga class, or learn more about Buddhism and meditation. The new Annex dorm is LEED certified and simply appointed. West St and Richmond Mountain Rd., Lenox, MA; 866-200-5203

The Mount Literary nerds will love touring Edith Wharton’s estate and lush gardens at The Mount. 2 Plunkett St, Lenox, MA; 413-551-5111

Shakespeare & Company The website really says it best: Shakespeare & Company “aspires to create a theatre of unprecedented excellence rooted in the classical ideals of inquiry, balance and harmony.” Year-round shows of Shakespeare classics and more. 70 Kemble St, Lenox, MA; 413-637-1199

Ventfort Hall A formidable Gilded Age mansion that, in the right lighting, can look downright fearsome. Check out the Gilded Age Museum and stay for a lecture or Victorian high tea. 104 Walker St, Lenox, Massachusetts; 413-637-3206

Norman Rockwell Museum This sweet little museum is stocked with Rockwell Americana and regularly exhibits the work of other illustrators. Tour the lush grounds and peek in on Rockwell’s painting studio, perfectly preserved as it was in 1960. 9 Route 183, Stockbridge, MA; 413-298-4100 x 221

Berkshire Botanical Garden A 15-acre garden and arboretum with over 3,000 species of plants on display. 5 West Stockbridge Road (Routes 102 and 183), Stockbridge, MA; 413-298-3926

Naumkeag Another Gilded Age “cottage” (apparently what they called mansions back then) coupled with spectacular gardens in Stockbridge. 5 Prospect Hill Road, Stockbridge, MA; 413-298-3239

Jacob’s Pillow Dance Festival The “hub and mecca of dancing,” according to Time magazine, this summertime festival is a must-see for any fans of dance, classical or modern. 358 George Carter Road, Becket, MA; 413-243-0745

North County

The Berkshires’ North County begins in the buzzing little city of Pittsfield and stretches north to the quiet cultural and outdoorsy outposts of Williamstown, North Adams and Clarksburg. Despite the presence of MASS MoCA — the United States’ largest contemporary art museum, situated in a 19th-century factory building — the pace here is slower, the destinations more far-flung and, in some spots, a little grittier. Many of these towns were once manufacturing epicenters, and they are now beginning to hum with life again after those industries left many years ago. If you like your getaways quiet and your high culture in small doses, North County might be the right place for you.

Places to Stay

Guest House at Field Farm This Bauhaus-inspired guest house is decorated with the stuff midcentury-modern dreams are made of, and it’s situated amidst hundreds of acres of gorgeous meadow, with the Berkshire hills rising up all around it. You can basically hike or ski right out the front door. 554 Sloan Road, Williamstown, MA; 413-458-3135

Bascomb Lodge A rustic wood and stone lodge built in the 1930s sits atop Massachusetts’ highest peak, Mount Greylock, over which miles of trails traverse. The simple, affordable rooms offer unbeatable views and spectacular star-gazing. In the morning, have breakfast with Appalachian Trail hikers while gazing down on the valley below. Mount Greylock, MA; 413-743-1591

Porches Inn The classic Victorian rowhouses of the Porches once housed millworkers, but you’d never know it. The place has been totally redesigned as a chic-yet-ironic boutique inn, where room service breakfast comes in a lunch pail complete with hot coffee in a thermos, and where you can tap happily away on your laptop in a rocking chair on the grand wooden porch out front. 231 River Street, North Adams, MA 01247; 413-664-0400

Places to Eat, Drink and Snack

Mezze Bistro + Bar Well-executed, seasonally-reverent food is the norm here, and the space and views are beautiful. If you forgot to make a reservation, wait at the knotty wood bar, where the bartender will concoct a house-made cocktail, like the snappy, Prosecco-kissed French 75. Use dinner here as an excuse to bring heels on your hiking trip. 777 Cold Spring Rd (Rt. 7), Williamstown, MA; 413-458-0123

Cricket Creek Farm A Certified Humane dairy farm with a charming country store selling raw milk, homemade cheeses (the Tobasi is to die for) and breads, local honey and jams, meats and eggs and the super-addictive Wilderness Fantasy cookies. Say hi to the pigs and chickens on your way out. 1255 Oblong Rd, Williamstown, MA; 413-458-5888

Lickety Split With two locations — one on Spring St. in Williamstown, the other in the MoCA complex — Lickety Split has the lockdown on homemade ice cream in North County. 1010 MASS MoCA Way, North Adams and 69 Spring St Williamstown, MA

Elf Parlor Hands down the best place for coffee in North County, hidden on a side street behind the state college. The fantastic espresso drinks and coffee are made from Barrington Coffee Roasting Company beans, and the baked goods (including vegan and gluten-free) are made with love. There is always great music playing here, along with free WiFi, and weekend evenings boast fun, lo-fi but energetic entertainment and local beers on tap. 303 Ashland Street, North Adams, MA; 413-664-7303

Brewhaha Right in town, just steps from MoCA, Brewhaha is always jumping. The coffee is strong and the breakfast is filling. Or swing by for lunch — the pressed wraps are chock-full of good-for-you ingredients with a dose of melty cheese. 20 Marshall St, North Adams, MA; 413-664-2020

The Golden Eagle The standard tavern fare here is unremarkable, but you won’t regret sipping a pint of BBC Steel Rail on the deck upstairs while taking in the amazing view over North Adams’ historic Hairpin Turn. 1935 Mohawk Trail, Clarksburg, MA; 413-663-9834

Stone Soup Vegan-friendly victuals and good, strong coffee in a super-friendly spot in charming downtown Adams. 27 Park Street, Adams, MA; 413-743-9420

The Old Forge You might have a hard time choosing from the mind-boggling array of draught and bottled beers available, so order a plate of wings while you narrow it down. 125 N Main St (Rt. 7), Lanesborough, MA; 413-442-6797

Café Reva This hole-in-the-wall spot is located off the main drag in Pittsfield and the wait for food can seem interminable, but the fare is a cut above the usual greasy spoon offerings. Rub elbows with the locals at the counter, and ask for real maple syrup on your pancakes. 238 Tyler St, Pittsfield, MA; 413-442-6161

The Lantern These char-broiled burgers are often cited as the best in the Berkshires, and it certainly doesn’t hurt that the space still retains some of that charming diner appeal. Outside, a pink neon sign beckons like it’s still 1926. 455 North St, Pittsfield, MA; 413-448-2717

Mission Bar & Tapas Pittsfield really starts to feel like a city when Mission is packed with people clinking wine glasses and picking at little plates of patatas bravas on a Friday night. 438 North Street Pittsfield, MA; no phone

Dottie’s Coffee Lounge Settle into a worn, granny-chic arm chair while you wait for coffee brewed from locally-roasted beans. The food here is straightforward and tasty, but it’s the comfortable atmosphere and the free WiFi that’ll get you to settle in. 444 North St, Pittsfield, MA; 413-443-1792

The Market A surprisingly upscale grocer in downtown Pittsfield maintains a hip vibe in this bright, window-lit space. Get a grass-fed beef hot dog, served with sauerkraut and stone ground mustard, and eat it while you stroll down revitalized North Street. 391 North St, Pittsfield, MA; 413-395-9766

Brix Wine Bar Brix serves freshened-up French classics in an endearing space that feels a little bit European with a small-town charm. 40 West Street, Pittsifeld, MA; 413-236-9463

Places to Shop

The Browns Stocked with classic but chic clothing and accessories including bags and device cases by design darling Orla Kiely. Stuff here is thoughtfully selected (with matching price tags) but the sale rack is a godsend. The staff is happy to let you shop in peace or coach you through trying on one of their well-made pieces. 16 Water Street Williamstown, MA; 413-458-1618

Toonerville Trolley An old-fashioned record store — you know, the kind with vinyl — in a rickety old Victorian in a tiny town in the Berkshires. Unexpected treasures can be dug up here, especially if your musical taste tends toward the weird and obscure. 131 Water St, Williamstown, MA; 413-458-5229

Where’d You Get That Intelligent toys for kids of all ages and personalized service to boot. 100 Spring St, Williamstown, MA; 413-458-2206

Hardware and MASS MoCA by Design These two MoCA-affiliated shops — one in the MoCA complex and on in downtown Williamstown — sell art and design books, kid’s toys and books, MoCA merch and other eclectic, well-designed goodies, like colorful tote bags from local creatives Blue Q. 1040 MASS MoCA Way, North Adams; 413-664-4481 x8140 and 50 Spring St, Williamstown; 413-652-2143

Shima Boutique Shima’s well-curated collection of kid, baby and maternity gear is design-focused, with an eye toward eco-friendliness, and the colorful, bright space is a real joy to visit, whether or not you have kids. Pick up a gift for someone little in your life. 105 Main St, North Adams; 413-346-1055

Papyri Books New, used and rare books in a cozy little storefront on one of North Adams’ most charming streets. Papyri also organizes literary readings and talks. 45 Eagle St, North Adams, MA; 413-662-2099

Persnickety and The Barking Cat One half of this Eagle St. storefront is a kids’ paradise, stocked with games and interactive toys, while the other half caters to the fur-kids set, with dog and cat treats and accessories. Persnickety also has a location in Pittsfield. 13 Eagle St, North Adams, MA; 413-662-2990 and 141 North St, Pittsfield, MA; 413-236-8697

Lynda’s Antique Clothing Loft Awesome selection of perfectly preserved vintage duds from the 19th to 20th centuries. 39 Park Street, Adams, MA

Emporium As peddlers of “a wondrous assortment of the unique and amazing,” the Emporium stocks stylish and design-conscious clothes, gifts, jewelry and other little treasures, some by local designers. 441 North St, Pittsfield, MA; 413-464-7914

Wild Sage Scour the collection of second-hand furniture and estate-sale castoffs to unearth an affordable treasure. Be sure to check out their second storefront, further up the street. 333 North St, Pittsfield, MA; 413-447-7000

Things to See and Do

Williamstown Theatre Festival Every summer, celebrated actors and other theater bigwigs migrate to the Berkshires for New York-caliber theater performed in the grand and intimate spaces of Williams College. WTF — as it’s known locally — acts as an incubator for promising theater and a showcase for works-in-progress.

The Clark The Clark is best known for its grand collection of French Impressionist paintings, and its contemporary collection is growing. The bucolic grounds are lovely to hike around after a trip through the galleries — be sure to take in the view as you head down the hill from Stone Bench. 225 South Street, Williamstown; 413-458-2303

Williams College Museum of Art Williams College’s small but well-curated museum often has several ongoing exhibitions culled from its huge collection. Plus, it’s free. Don’t miss the giant Louise Bourgeois eyes sculptures adorning the grassy slopes out front. 15 Lawrence Hall Dr, Williamstown; 413-597-2429

Images Cinema Rainy night? Instead of sitting around a hotel room, check out a film at this cozy indie cinema on Williamstown’s tiny main drag, and get a bucket of GMO-free popcorn topped with real butter and garlic salt. 50 Spring St, Williamstown; 413-458-5612

MASS MoCA The sprawling 19th-century buildings that make up this contemporary arts mecca — the largest of its kind in the U.S. — were once factory buildings churning out textiles and electronics. Now, rotating contemporary drawing, painting and photography exhibitions sit juxtaposed with large-scale and site-specific installations, including the jaw-dropping Sol Lewitt wall drawings, which are on display for 25 years. Year-round performing arts events liven up the weekends with out-of-the-ordinary live performances and rare treats, like cult films with live orchestration. A must-visit. 87 Marshall St, North Adams; 413-662-2111

Windsor Mill, Eclipse Mill and Beaver Mill Just outside of town, along the Mowhawk Trail, you’ll find these three repurposed mills, now functioning as studio and gallery spaces and live-work lofts. It’s worth exploring here, not only to see what’s happening in the simmering independent art world, but also to see the imposing structures themselves. Highlights include the Kolok Gallery in the Windsor Mill; in the Eclipse Mill, don’t miss G.J. Askins’s collection of art books (Loft 108) and Union & Field (Loft 243, opening in October); and the Beaver Mill features Frog Lotus Yoga, Studio 21 South and Gravity Press. Every year in mid-October, artists in all three mills (and elsewhere in town) throw open their doors for an Open Studios weekend. Right next door to the Beaver Mill, explore the lovely trails and natural amphitheater (complete with MoCA-related sound installation) of Natural Bridge State Park.

DownStreet Art DownStreet Art brings the sleepy streets of North Adams alive with strolling pedestrians checking out visual art, sculpture and performance in the galleries and storefronts downtown. Ride the art trolley to the more far-flung destinations, or stop in at the Hub for a pint.

Third Thursdays On Third Thursdays, downtown Pittsfield becomes the impromptu setting for musicians, artists and craftsmen, and alfresco diners spill out from the restaurants on North St. Stop in at one of many galleries, and check out public art installations along the streets.

The Copperworks A ramshackle, post-industrial setting for indie/punk shows and movie screenings. At the Mount Eerie show I attended, the hushed hipster audience was reverent — Pabst cans and DSLRs in hand and mobile phones on mute. 34 North Pearl St, Pittsfield; 413-329-6793

Alchemy Initiative This space, converted from a former Catholic church, calls itself an “Intentional living laboratory” and offers urban farming and DIY workshops to the community. Take a tour during open studio time, or check out the events listings to see what’s happening. 40-50 Mellville St, Pittsfield; 413-236-9600

Arrowhead This 1783 farmhouse was home to author Herman Melville and where he composed the classic, Moby-Dick, and many other works. 780 Holmes Rd, Pittsfield, MA; 413-442-1793

Hancock Shaker Village The Shakers, an 18th- and 19th-century religious group, called this community a “City of Peace.” Revisit a much simpler time in life, and explore some of the earliest examples of simplicity in American design. 34 Lebanon Mountain Rd., Hancock, MA; 800-817-1137

Get Outside

You could come here without hiking, biking, skiing or snow-shoeing gear, but that would take some of the fun out the experience, wouldn’t it? The famous Appalachian Trail runs right through Berkshire County — hike at least a few steps of it, just so you can say you did.

Mt. Greylock State Reservation The switchback road up to the top of Mt. Greylock (begin at Rockwell Rd. in Adams, or Notch Rd. in North Adams) rewards with awesome vistas and pull-offs for snapshot-taking. For the more athletically inspired, try the Thunderbolt trail, a vertiginous hike up a 1930s ski trail — complete with ski lift ruins — that begins in the bucolic Greylock Glen, in Adams.

Ashuwillticook Rail Trail Work off that museum fatigue with a stroll or bike ride down this level 11-mile trail, which extends from Adams to Lanesborough through gorgeous landscapes and past several lakes where canoeing and kayaking (and ice fishing!) are popular pastimes.

Savoy Mountain State Forest The beautiful and off-the-beaten-path Tannery Falls hike is worth the scenic and twisty drive up Route 2 from North Adams. Check out the giant Balancing Rock on your way out, or stop for a dip at scenic North Pond.

October Mountain State Forest This 16,500-acre park, named by Herman Melville, is the largest in Massachusetts, and includes access to hiking, camping, swimming and cross-country skiing.

Skiing No, there isn’t snow on the ground yet, but ski season here can start as early as November. Generally, skiing here is small-scale and relaxed. Try Catamount, Butternut, the somewhat resort-y Jiminy Peak or the off-the-beaten-path Berkshire East.

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  • What a wonderful job Fran! You captured all of my favorite places – I love seeing a place that is so special to so many find it’s way to one of my favorite websites. Excellent to guide to an excellent place. I wish I was at Dottie’s right now… xo

  • thanks for a great overview! In a couple of weeks I’m taking my first trip to the Berkshires (Lenox) with the Boyfriend. I will be sure to revisit this guide for tips!

  • We went to the Berkshires for the first time this past summer for a cousin’s (mind blowingly gorgeous) wedding, and I loved the area! I recommend Gedney Farm as another place to stay and enthusiastically second the recommendation for Baba Louie’s. We managed to eat there twice on our very short stay; best pizza I’ve ever had!

  • I’m a Western Mass resident myself– the Berkshires are really lovely and deserve this well-done spotlight– though I’m much more a fan of the Pioneer Valley (Northampton, Amherst, Springfield-metro area). Maybe a “guide to the Pioneer Valley” next? Adams may have Edith Wharton, but we have Emily Dickinson. :)

  • My friends got married this summer at The Mount and it was absolutely magical. I’m from CT, but never fully experienced the Berkshires until recently. It’s a lovely place, especially in the fall.

  • i used to live in williamstown and this brings me back. lots of places here i’ve never been to and i will use this list next time i visit. thank you! (ps- frances is my favorite name:)

  • GREAT WRITE-UP! Even from an experienced Berkshire-ite, there is still stuff I have never heard of. We will share this with our hundreds of families who visit the Berkshires every summer.

  • I stopped into Lynda’s Antique Clothing Loft on my run last week. I’d never been in and was kicking myself for not bringing $. As my friends know, I’m not a real vintage type girl, but wow! I’ll be going back to mix and match aprons and linens for Christmas presents and have ordered my husband to fetch a charming hat for my present this year.

    Well done Fran, glad I get to live here!

  • What a thorough and useful guide! I live in the Berkshires and I will keep this article in my bookmarks to pass along to people who are coming to visit! Thanks for getting the word out on all that this beautiful and fun county has to offer!

    • hi guys-

      i’m not familiar with 99designs, but i’m going to touch base with andrea about this and look into the company myself. i trust andrea’s opinion and her support of the indie design community immensely so i’m going to look into your claims before responding either way. i don’t think andrea would knowingly recommend something that is hurtful to indie designers.

      that said, i understand the issues that people take with low cost or “cheap” design studios. i have the same issues with writers that low-ball their writing fees and lead to people asking us to write things for free or for $25 for magazines, etc.

      that said, i do think that everyone, regardless of budget, deserves access to information about branding resources. if a new business only has $100 to spend and can find a place to work in that budget, i want them to have that resource (if there really is some illegal sweatshop situation at those places then of course i wouldn’t want to endorse that). but i also want them to know that it’s worth saving up to hire someone who can give them a higher quality of work and customer service. and we’ve spent the last few years of this column talking about the importance of investing in services like this. that said, we’re always emailed on a daily basis with requests to cover business service options for people who are running on little to no money. so i want people to have all the options out there. that said, if the quality of work from (or the working conditions in) this particular shop are truly a problem (which i’m looking into today) we will be sure to update the post or provide some sort of additional information.


  • Lived in the Berkshires for 3.5 years myself in the late 90s/early 00s when I worked at Jacob’s Pillow. Dirty Bruto pizza at Baba Louie’s is THE best!!

  • Hey folks! Thanks for the kind praise! Word on the street is that, sadly, the Copperworks (in Pittsfield) is now defunct. BUT, if you’re coming this way, you should check out the Pittsfield Contemporary Dot Com Gallery, which apparently has a lot of the same folks involved.

    I also forgot to mention Bizalion’s in Great Barrington, which is somehow straight out of France — cheese, pate, and baguettes included. Plus, you can buy olive oil buy the ounce. Yum.

  • Thanks for this post!! My husband and I have lived in the pioneer valley for about four years now, but haven’t explored the Berkshires. We’ve been planning a trip for the first weekend in November and this guide was posted at just the right time!! Thank you!

  • I live just over the border in NY and I’m so happy to see you give some love to Mission Bar – I love it – everytime I go to pittsfield for Barrington Stage or anything else I manage to stop in and get something yummy to eat and drink!

  • This is fabulous! I was born in “GB” and spent my formative years on Railroad Street. Is 20 Railroad still the best place to get a buffalo burger? Is Mistral still there? It’s been way too long since I drove over 23 into South County. Thanks muchly!

  • Lived in the Berkshires for three years, and I can’t possibly give enough praises to the Route 7 Grill. It is singlehandedly the establishment I miss the most. The mac and cheese is amazing, as mentioned, but so is everything else they make. Go check it out!

  • Friends and I have a girl’s weekend twice a year in the Berkshires, perfectly situated between Boston and Philadelphia, where we arrive from. There are always charming cottages and homes available to rent, even for a weekend. It’s simply one of the most relaxing and wonderful places. Julia, your description and recommendations are spot on. Just to add another category….breakfast: Haven Cafe + Bakery in Lenox is so tasty, and in summer, it’s quite the place to see and be seen. Caffe Pomo D’Oro offers European charm right by the train station in W. Stockbridge. Can’t wait to head back for a snowshoeing excursion this winter!

  • Great list. The Berkshires is a truly special, magnetic place with all sorts of gems tucked among our hills. We are so lucky!

    One of my favorite spots is Café Adam in GB–a cool Euro-bistro off Route 7 just north of downtown, with fresh, farm-to-table fare, excellent cheeses and wines, and stellar desserts. And as it’s in the Berkshires (read: uber-casual, even at most upscale restaurants), perfect for popping into after a hike up Monument Mountain.

    Neada: 20 Railroad survives with its great pub grub (though the Whippoorwhill Burger at Allium is truly to-die-for), but under new ownership (by the folks of the long-defunct Dragon Restaurant in Pittsfield…which is supposedly being reincarnated as the Dragon Steakhouse). Mistral is still there, too!

    Karen Allen–of Indiana Jones fame–has a fiber-arts shop on Railroad Street, too, and, right around the corner on Main Street, Robin’s Candy Store tempts passersby with its encyclopedic array of goodies straight out of Wonkaland….

    Love this place.

  • My parents own a one room schoolhouse in Pittsfield. It is the former Morewood School built in 1843 and they currently rent it out for visitors to the area via VRBO (#310035)- it is a charming place!

  • Thanks Frances! I’m always looking to try all the great spots in the Berkshires since I’ve moved here. There is so much left to do!

  • Not a bad review of the area, but unless I missed something you left out Sheffield. There is the Market Place Cafe, which rocks! Also, Dewey Hall has a monthly folk music concert the first Saturday of every month (except July and August) with fabulous refreshments and it’s only $10! Not to mention the newest store/healing space called Awaken Healing Arts with lovely ladies who do acupuncture, massage and reflexology. Plus groovy spa like bath things and lovely clothing from eco designers. And last but not least, antique alley. Route 7 is basically an antique buyers dream! Not to mention the trails around here, Bartholomew’s Cobble being just one with year round programs and hiking, show shoeing, etc.. I’ve lived here for 15 years and just thought you’d like to know.

  • Oh my goodness! I was JUST in the Berkshires for the very first time last week. On Thursday I visited the Hancock Shaker Village that was sited and LOVED IT! It is so beautiful there and I learned a lot from a much simpler way of life. I spent some time in Northhampton as well. I’m a southern girl, so the autumn foliage was unlike anything I had ever seen. How wonderful!!!!

    P.S. I also enjoyed the Eric Carle (children’s author) museum on the Hampshire College campus!!!

  • Fantastic guide! I went to school in the Purple Valley and really miss living in a place so darn beautiful. Especially when fall rolls around… Sniffle…


  • Quite a nice guide but you left out Barrington Stage Company in Pittsfield and Berkshire Theater Festival in Stockbridge. Also there’s an incredible cafe in Lenox named Haven Cafe & Bakery which serves wonderful local organic food cooked perfectly. A great place to go for Sunday Brunch or some of the best coffee in the state.

  • Wonderful job on an overview of the Berkshires. As a resident, it’s great to see some favorites highlighted. I’m particularly happy that Pittsfield has once again become a destination thanks to the revitalization and the blossoming arts community. Spot on!

  • another “happy valley” (i.e., amherst/noho resident) who thanks you for this post. having said that, many of the activities and events mentioned actually take place in the summer months. the berkshires is lovely for skiing in the winter, but not much going on in tanglewood or with local theatre festivals when the cold moves in.

  • I spent my middle school and high school years in the Berkshires so a big piece of my heart remains there. I’m glad that someone else mentioned the Berkshire Playhouse. I’d like to add a few more tips- Don’t miss the shops of Stockbridge or live music at the Lion’s Den. A lovely fall, spring or summer day demands a visit to Stockbridge Bowl, Ice Glen, Bish Bash Falls, or take a hike up Monument Mountain to Squaw Peak, if you’re able. The views are spectacular! Chesterwood is an absolute must… Another lovely place to stay is Blantyre Castle and, if you can swing it- Hancock Shaker Village and the Williamstown Theatre Festival are a scenic drive away. You brought so memories back for me today, Frances. Thank you!

  • This is quite the lovely guide, and I compliment you on its thoroughness. Of course, any place as culturally rich as the Berkshires will provide too many things for anyone to list them all.

    So a quick shout out for Berkshire Theatre Festival in Stockbridge, which is the oldest cultural institution in the region (founded in 1928) and one of the oldest regional theatres in the country. We produce shows from May through December and still utilized the original playhouse as designed by Stanford White.

  • this is so great!

    i went to college at simon’s rock in great barrington and lived above soco creamery on railroad so the berkshires are near and dear to my heart.
    my husband and i like to take a trip up every year around our anniversary so this will come in handy in the spring!

  • My wife and I are Brits who’ve had a love affair with New England since the mid-1990s. A couple of years ago we decided on a career change and have been working on a business idea that offers the new generation of travelers 21st century accommodation in décor, experience, brand personality and – importantly – comfortable affordability. Using buildings that already exist. We’ve earmarked The Berkshires as the location for the first of these, hopefully opening summer ’11. I think/hope that this thread shows that there are plenty of younger travelers discovering or rediscovering the area, which is so easily accessible from NYC and Boston. During our development phase we’ve spent a lot of time with political, business and property big cheeses in Pittsfield, and certainly accommodation is rather restricted to chintzy historic B&B’s, or cookie-cutter chains, targeting richer snowbirds or people on a budget passing through. Stonover and Porches are rightly name-checked. The former is beautiful if you’re looking for expensive, restrained style at the top end of the B&B price range. Porches is cool if you want to visit MASS MoCA or The Clark, as its right at the northern extreme of the County. We feel that the area is on the cusp of attracting a new wave of design-conscious travelers and pleasure-seekers who are drawn to the culture, cuisine and amazing scenery, be it to ski, cycle, hike, canoe or just stand and stare. I’m happy to read that others out there feel the same way. So watch this space. Well, not this space, but you know what I mean.

  • There are lots of places to visit and see in the berkshires but I do believe that the most unique site to visit is the Gingerbread House in Tyringham. My husband and I just got married at the estate in September and it is truly a one of a kind site. Definitely worth the 10 minute drive from Lee!

  • Love to see our area getting a design*sponge shout out! Dreamaway is one of the most special places to have a wild cocktail, eat a great meal, hear some live music, and sit by the outdoor fire pit. Also: Race Brook Lodge is where my husband and I celebrated our engagement four years ago – it is one of the more affordable and relaxed (if sometimes too relaxed) options for the area – and the Stagecoach Tavern next door is great for dinner, too. And love Germain, Rubi’s, WTF, Tanglewood – come on up everyone!

  • this is great, i went to Berkshire School, a private school in the town of Sheffield. It was good times. Spent a lot of time in the Great Barrington town on the weekends and the town of Stockbridge.
    Barrington Brewery and Bizen Japanese Restaurant are two of my favorite place to have a bite on the weekends.

    The Egremont Inn was a very nice cozy little inn and such a sad when i heard it got burn down.

  • If you’re in North County, stop in at Tunnel City on Spring Street in Williamstown after visiting the Clark or the Williams College Museum of Art. Great people watching, and a perfect coffee shop atmosphere!

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  • I’m surprised that the Gateways Inn & Restaurant is not included in the list of places to stay. It’s a historic bed and breakfast right in the heart of downtown Lenox, plus it also has a restaurant and lounge with live music on the weekends.

  • Don’t forget your local handmade shop Kit & Kaboodle located just 2 min away from MASS MoCA on Holden Street. We are neighbors to PUBLIC Eat & Drink. We showcase handmade items from local artists & crafters. #Shoplocal #intheberkshires #kitnkaboodlena

  • We love Ms. Duncan’s Berkshires 101 Guide!! Over the winter there have been changes in Lenox and we hope your readers will discover the many NEW Shops/Galleries that make Lenox an exciting place to visit. Check out SHOP LENOX on Facebook.