Editor’s note: This article is taken from the current issue of Berkshires Calendar magazine, a free publication of The Berkshire Edge which you can pick up at some 140 locations in and around Berkshire County. This print magazine focuses on places to go and things to do.  Pick up your copy today.

“What I’ve been talking about amongst my wonderful cooking friends is how out of practice we feel coming off the COVID year, and how to find a way to make it all simpler,” says Maria Nation, an avid host, accomplished screenwriter, and co-founder of Good Dogs Farm in Ashley Falls. “No elaborate dishes—just a bowl of soup, a glass of wine, and good friends. Honestly, that would be a perfect dinner party.” 

Surely, a long stretch of social distancing and separation has brought the “purposeful party” into sharper relief. The focus is as much on the who—whether that’s two, ten, or twenty people—as on the what, when, and where. These days, being together is where it’s at! 

The Berkshires has been a gathering spot for ages. Gilded Age tycoons held lavish soirees at their “summer cottages,” dancing the quadrille into the wee hours. And not just during the usual season—by the early 1900s, the Knickerbocker set betook themselves here to ring in the New Year with abandon. By all accounts, these geographical ancestors really knew how to have a good time.

Edith Wharton, herself a 40-something NYC expat, famously held court at The Mount, impressing fastidious Henry James with her hospitality know-how. For Wharton, whose novels dripped with dialogue (she described her role as “merely a recording instrument”), lively discourse was the raison d’etre, not the roasted pheasant or Château d’Yquem—though she is purported to have greeted visitors with bubbly to wash down the bon mots. 

That esprit de corps is on a continuum, linking past and present. People still flock to the Berkshires for the same reasons—a lovely setting and a cerebral populace—only without an army of staff or a proclivity for ostentation. Like Wharton, modern-day hosts find joie de vivre in being in the company of others—no cultural dexterity required.

“With its larger kitchen and actual dining room, our Southfield home is more conducive to entertaining than our small Manhattan apartment,” says longtime beauty editor Jane Larkworthy who, with husband Bertrand Garbassi, moved to the Berkshires full time during the pandemic. The back porch has also been a “godsend,” and once the temperature drops she brings out electric heaters and cozy blankets.

After a gung-ho start—”we were like the new kids on the block trying to impress everyone by making eight dishes, which was way too much and exhausting!”—the couple is now more inclined to ping three people the day before and then pick up frozen ramen from Guido’s. “We are not big on lead time.” Nor is Nation. She finds the most memorable “parties” are the ones that occur organically—such as when friends drop by unexpectedly and you rummage in the refrigerator for leftovers. “Zero planning, zero stress, maximum friend time. That is the ultimate goal of any dinner party.” 

Even maximalist Martha Stewart—whose first country retreat was a one-room schoolhouse in nearby Middlebury, Mass.—wrote, “I think of entertaining as one friend treating another friend” in the original Entertaining (in 1982!). “What matters most is not elaborate technique or pomp or show but warmth, thought, and a sense of your individual style.” In modern parlance, be authentic—or “you do you.” For some that means preparing an elaborate smörgåsbord (or, say, Martha’s Country Pie Party for Fifty) and for others serving spiked hot chocolate and pfeffernüsse around the firepit.

How does this approach play out at Thanksgiving, the archetypal dinner party? View that feast as America’s original potluck—the Wampanoag Native Americans brought deer, fish, and native crops, the pilgrims wild fowl and vegetables from England. Delegating is another way of honoring tradition; in a sample scenario, you roast the turkey and set the table (and handle cleanup), your guests contribute the sides and desserts. Gratitude will flow this way and that. 

Other ceremonial repasts—whether they mark Feliz Navidad, Hanukkah, or Kwanzaa (culminating in Karamu on New Year’s Eve)—can be equally equitable. People want to pitch in! No judgment of course if you prefer to DI(all)Y. Just know that most guests relish sharing a family recipe or a store-bought some such. Then again, with all the great food purveyors in the Berkshires, you could easily feed a crowd without cooking a thing—and support these small businesses to boot!

Lean into all the Berkshires has to offer. Here you are motivated to seek out the handcrafted rather than the high falutin’, the small batch over the mass produced—and above all, food with a farm-fresh pedigree. That ingredient integrity is what the area is prized for, and it provides a connection to the community writ large. 

Indeed, “holiday feasts are perfect moments to celebrate our farmers, who grow such beautiful food throughout the year,” says Alana Chernila, cookbook author and marketing manager for Guido’s Fresh Marketplace. (She is espousing this idea in a class on “vegetable-focused share food” at Berkshire Botanical Garden.) “When we move meat to the side, it gives us the opportunity to really celebrate the vibrant colors and deep flavors that only vegetables can bring.” (Vegans and vegetarians will applaud these efforts.)

Of course, produce is not the only pride of the Berkshires. Plenty of farms produce humanely raised, pastured poultry, pork, and beef. It is more costly but consider the superior quality a special-occasion expenditure; you also will be sustaining the local agricultural economy.

And remember: Entertaining is, yes, about laying out a delicious spread, but only insofar as it is the tasty, tippling means to a few hours of rubbing elbows (the new way to hug!) with your nearest and dearest—the worthwhile “end.” Cheers and glad tidings!

Where to Find Great Stuff for Entertaining

As you peruse the resources that follow, keep in mind that a good many straddle more than one category—and that all attempts were made to note the overlaps. 

HOLIDAY HEADQUARTERS

Guido’s Fresh Marketplace (Great Barrington, Pittsfield). Though this emporium hardly needs any introduction, the stores the Masiero brothers have built are where cooks go for superlative fresh produce and premium shelf ingredients, along with house-baked goods, cheese, and spirits—plus choice cuts from Mazzeo’s Meat & Seafood counters.

If take-out is more your speed, you’ll find an abbondanza of prepared foods—everything from salads to sushi—and even all, or part of, your Thanksgiving feast, including Mamma Mazzeo’s popular sausage stuffing and scrumptious desserts. (Order early!)

And this just in: A full-size version of The Chef’s Shop will be taking up residence in the expanded Great Barrington location, where you can find all things kitchen and tabletop under the same roof as those top-notch foodstuffs. 

FRESH TURKEY 

A big plus of living in the Berkshires is being able to score a heritage bird from a local farm—assuming you don’t delay (some start taking orders as early as September). And if the turkey doesn’t work out, you can still purchase roasts and hams to serve at other celebratory meals.

By no means exhaustive, these farms are notable for their turkey trade: Moon On The Pond in Sheffield; North Plain Farm in Great Barrington; and Red Shirt Farm and Square Roots Farm, both in Lanesborough. It’s a tight-knit group, so if one is sold out, they might recommend another. 

Otherwise, you can order fresh turkeys from Guido’s while they last or choose from a wide selection of organic birds. Berkshire Co-op Market (Great Barrington) and Wild Oats Market (Williamstown) also offer organic turkeys by order. It bears repeating: Do not delay. 

If all else fails, or if the turkey is not “all that” in your estimation, turn to family-owned Big Y supermarkets, which are “big” but not overbearing—even procrastinators are sure to find a turkey (maybe frozen) while being able to check off the rest of your shopping list in one fell swoop.

THANKSGIVING PIES

Preparing the holiday feast is work enough—why not save your efforts (and oven space) by outsourcing the pies? The scratch bakeries below make their items daily, but you’ll need to place an order to ensure availability during the holidays.

The apple, pumpkin, and mince pies (among others) from Taft Farms (Great Barrington) are downright famous, as are the baked cider donuts, muffins, and giant cookies (hello molasses ginger!). The farmhouse kitchen will even prepare the entire holiday meal for you, using its own produce and other local ingredients.

The aptly named Haven Café and Bakery (Lenox) cranks out Thanksgiving specialties like Pear Cranberry Galette, Apple Cake, and Pumpkin Crunch Torte, in addition to its coveted biscuits and scones. Or order their Thanksgiving dinner to-go, complete with turkey breast and all the fixings.

Thanksgiving desserts from A-Frame Bakery (Williamstown) run the gamut from Pear & Almond Tart to Pumpkin Cheesecake with Ginger Pecans and GF Chocolate Decadence Torte. December brings iced sugar-cookie stars for Hanukkah and Black Forest Buche de Noel for a yuletide celebration. Oh, and chocolate truffles for all occasions.

COOKING TOOLS & BAKEWARE

Even if you are a veteran host, you might need to pick up a few new provisions—more so if you are entertaining for the very first time (or in a long while). 

Popular items tend to fly off the shelves, so scurry to Different Drummer’s Kitchen—
The Cook’s Resource (Lenox) for an impressive, well-organized inventory of basic and specialty kitchen equipage, including everything you need for Thanksgiving—twine, basters, gravy boats, pie weights—and beyond. Snowflake rolling pins? Check. Smeg Stand Mixer? Yes, please!

In addition to honing your skills in one of two teaching kitchens, visit HSG Home Chef (Hillsdale)—which inhabits a can’t-miss pink house on Route 23—for its extensive cookbook selection, abundant cookware, and gadgets galore, plus a complete line of Ann Clark cookie cutters for holiday bake-offs. Then cross the street to browse the curated collection of vintage and “old-style new” home goods—pre-seasoned cast-iron pans, a bevy of bar tools, and retro party games—at Hillsdale General Store (by the same proprietor), a smartly restored circa-1850 five-and-dime.

TABLETOP & SERVEWARE

The Berkshires is home to cultivated brick-and-mortar shops (and their online portals) that rival anything in metropolitan areas for stocking artisanal pieces with a penchant for provenance.

Designer haunt Hammertown (Great Barrington) has, as highlights, handstitched table runners, stone-washed linen napkins, wooden salt and pepper grinders, hammered copper pinch bowls. and mix-and-match dishware in shades of indigo, as well as stylish potholders (for those oven-to-table moments). 

Sett (Great Barrington) specializes in bespoke items with a backstory—rope trivets, block-print table linens, woodland-themed dinnerware, hand-forged cheese knives paired with locally-made wooden cheese boards, and adorable salt cellars.
It also carries tapers and distinctive flatware sets.

The motto of Design Menagerie (Lenox) is “Objects of Utility and Beauty—extraordinary things that elevate ordinary tasks,” with an emphasis on emerging artisans. On display are platters, pitchers, bud vases, and leather-handled trays in organic shapes and a timeless shade of white—all the easier to integrate into your own collection. 

HOLIDAY SWAG & DECOR

When there are halls to be decked, residents here flock to their trusted family-owned nurseries for festive finery (and fresh-cut trees). If you haven’t already, it’s worth starting your own family tradition.

Ward’s Nursery (Great Barrington), now in its 64th year, is home to a bustling Christmas shop come November and December, with ornaments and other tree trimmings and fresh wreaths. Rather create your own? They’ve got the supplies for that too.

Post apple-picking season, Windy Hill Farm (Great Barrington) transforms its retail center into a jam-packed Holiday Shop replete with boxwood and all things winterberry, amidst decorated trees (for inspiration), tabletop arrangements, and other delightful decor. 

Third-generation Whitney’s Farm Market & Garden Center (Cheshire) does a brisk off-season business selling boxwood kissing balls and other seasonal greenery. You can also order fresh turkeys and holiday hams. (Order early.) 

NIBBLES & NOSHES

Whether you are hosting people for drinks, dinner, or the whole weekend, you’ll want stylish bar snacks that are easy to pull together—and easy on the eyes. 

Locals in the know swarm to Rubiner’s Cheesemongers & Grocer (Great Barrington) for tutti cose Italiane—cheese, of course, but also a supporting cast of salumi, pâtés, and chocolates (plus panettone, as a holiday addition.) It also traffics in a nuanced selection of natural wines. Not sure where to begin? Order up a custom cheese and charcuterie board. And be sure to nab one of the gift boxes for a lucky host.  

Besides a stellar assemblage of spirits, the sibling Nejaime’s Wine Cellars (Stockbridge and Lenox) offer a comprehensive “grab-and-go” selection of cheese (over 100 types!) and all the accoutrements, in addition to Lebanese specialties and a surfeit of sweets. And their ready-made gift baskets, with wine-and-food pairings, will get any party started—even your own.

The Cricket Creek Farm Store is worth a drive to Williamstown for its own award-winning cheeses—the creamy, briny, crumbly feta has a cult following—as well as pastured beef, veal, and pork. The self-serve, honor-system shop also stocks products by local vendors, including Hosta Hill kimchi and Backyard Brine pickles. 

WINE & SPIRITS

Wine may be your first choice when entertaining, but beer is just as food-friendly and goes especially well with cheese and charcuterie. 

Because, get this: The Berkshires is brimming with small-batch breweries—Barrington Brewery, Big Elm Brewing, Bright Ideas Brewing, Shire Breu-Hous, Wandering Star—each with its own taproom, though you can find their cans at local retailers too. 

Family-owned Domaney’s (Great Barrington) has a vast, deep selection of wines from around the world and a friendly, knowledgeable staff to guide you. (Ask to see the premium wines upstairs if you are looking for a splurge.) The craft beer selection can’t be beat.

Conscious consumers will appreciate the sustainability ethos of Départ (Great Barrington), a boutique retailer that focuses on “small, multiply marginalized and under-represented winemakers, family-owned producers, and [wines made by] responsible methods.” Be sure to ask the resident sommelier for recommendations. 

Likewise, South Egremont Spirit Shoppe spotlights small-production wines for people “who care about what they drink, where it comes from, and who is making it.” The owners—both with wine-industry cred—will happily share their enthusiasm for a rare find. Shop(pe) here, too, for crisps and crackers, cheese and charcuterie, and other goodies.

Go straight to the source for first-rate spirits by Berkshire Mountain Distillers (Sheffield), all handcrafted at the county’s first legal distillery since prohibition. Greylock Gin, Ragged Mountain Rum, and Ice Glen Vodka are among the core offerings. New for 2021 is a limited series of whiskeys in collaboration with local breweries. Stop by for a tasting, then drive five minutes to The Pass, a recreational dispensary to sample “farm to label” cannabis. 

HOLIDAY SWEETS 

It helps to have the following sweet spots on speed dial—or as saved GPS destinations—for all your festivities, including any impromptu get-togethers.

An offshoot of Old Inn on the Green, The Southfield Store (Southfield) is a winsome brunch spot in a one-time general store that draws locals and tourists. A slate of specialty cakes and pies are available by phone order, or make your way here via scenic country roads for a daily roster of baked goods (also available by special order).

The Lost Lamb (Stockbridge), directly across Main Street from The Red Lion Inn, serves up Parisian pastries with Norman Rockwell views. Buy dozens of the macarons in a variety of flavors to carry you through the Festival of Lights—or for a New Year’s Eve dessert party. Specialty cakes are sometimes available, too, depending on demand. (Note: Orders are only taken in person.) 

Legendary for its sourdough boules and chocolate bread, Berkshire Mountain Bakery (Housatonic and Pittsfield) adds traditional panettone and stollen to its regular lineup this time of year. May as well buy the ready-to-bake, seminal pizza, too—or pick up the makings (crust, sauce, cheese, and other toppings) and do the honors yourself. 

Since opening in 2003, Chocolate Springs Café (Lenox) has earned serious chops for its hot chocolate and velvety mousse cakes—and the open kitchen where you can see the inner workings. Chocolatier Joshua Needleman also deploys distinctive bars (such as the celestial All-Nighter Bar and gold-dusted Celebration Bar) and striking truffles with a Euro-Japanese bent.

GIFTS FOR THE HOST 

A new outlook on entertaining calls for a host-gift overhaul. Exceed expectations with a novel token of your appreciation.

Owned by the event-planning duo behind “Only in Your Dreams Events”, The Shop (South Egremont) carries party-ready “packs,” which you can feel good about giving—the price of most includes a donation to a designated charity, such as the Restorative Justice Pack (to benefit Multicultural BRIDGE). The must-see back room has holiday games, décor, and whimsy aplenty.

A present from Campo de’ Fiori (Sheffield) will delight any plant lover—no green thumb required. In lieu of cut flowers, co-owner Barbara Bockbrader can create a custom bouquet using dried (“everlasting”) botanicals—or assemble it yourself in one of their mercury-glass beauties. Amaryllis and paperwhite bulbs (potted or not) are other gifts that keep on giving.

Handsomely packaged candles and diffusers are just some of the reasons to shop at One Mercantile (Great Barrington). Others include bird-themed glassware designed in-house), hand-printed kitchen towels, illustrated calendars, and seasoned salts. Or be the bearer of cocktail mixers and syrups, such as Bootblack’s Ginger Cardamom Lime—just add booze!

Adjacent to Hotel on North, Dory & Ginger (Pittsfield) is not just for out-of-towners. Residents come here for Berkshire-themed items, along with a smattering of linens, glasses, dishes, serving pieces, and cutlery, plus festive decorations for tabletop and elsewhere. 

Next to the Berkshire Museum lies the retail store for Museum Outlets (Pittsfield)—a labor of love by the two-generation family that runs it. What started in their own home in 1992 is now a full-fledged plant in a turn-of-the-century textile factory, where custom-designed cards are printed, one color at a time, on two letterpresses, and mirror and picture frames are crafted by hand.