Looking for Your Wintersports Hookup in the Berkshires? 17 Food and Drink Tips

While the recent dumping of snow have caused chaos for school buses and highway departments, they also sweeten the mountain conditions throughout the tri-state area. While staycation-seeking skiiers can hit slopes in the Catskills, Adirondacks, Vermont and even farther north, our go-to has been Catamount Ski Area in Hillsdale, New York. Only about 250 miles, as the crow flies, from eastern Long Island (less from New York City), Catamount is not only in the great state of New York, it’s also affordable, family-friendly (read as: great ski school options), close to Great Barrington, Mass. (our favorite small town away from our small town) and in the midst of the fantastic food and drink options of the hipster-meets-back-to-the-lander Berkshires. Here are 17 tasting tips, centered on Great Barrington, to consider on your next Berkshires getaway. (If you’re putting down deeper roots in the region, check out our sister magazine Edible Berkshires.)

Best Bagels

Great Barrington Bagel Company

Start your day, or pick up a house-warming dozen, at the Great Barrington Bagel Company, a slice of Russ & Daughters in the mountains, complete with Acme smoked fish, appropriately sized bagels and gallons of matzoh ball soup.

Best Morning or Apres-Ski Nosh

Oliva Provisions and Monterey Chevre

Must have toppings on your Berkshire Mountain Bakery loaf, the kale and garlic dip from Oliva Provisions in Ancram is addictive. The clean, crisp chevre comes from the goat farm down the road in Monterey.

Best Cereal


Founded by a pioneering Berkshire chef who opened a bakery and several celebrated restaurants in the region, Bola Granola wins fans for its generous use of nuts and seeds. Epicurious said it “melds sweet and salty into one crunch of edible love.” Buy more than you think: it works for breakfast, lunch, dessert and skiing snack.

Best Local Grocer

Guido's Market local label

One East End transplant described Guido’s Fresh Market as what would happen “if Citarella’s and Whole Foods had a baby.” The popular, locally owned grocer, with locations in Great Barrington, Pittsfield and beyond, features small regional brands (along with food miles labeling), an impressive produce and meat sections, and a full wine, beer and spirits section, with all the right Northeast booze. (Hint: 10% your bill when you show a Catamount ski ticket.)

Endless Aisles of Regional Suds

Cambridge Brewing Company bottles at Guido's

Among the Massachusetts-brewed beers you will find at Guido’s and around town is Big Man IPA from Cambridge Brewing Company.

Best Food Coop

Kombucha taps at Great Barrington Food Coop

Among the New England institutions we are jealous of is the small-town food coop. Whether in Ithaca, New York or Burlington, Vermont, they always impress with their selection and prices and we cram our car with groceries for the trip home. The Great Barrington Food Coop doubles the envy with the sorts of produce, dairy and meat that would make a Park Slope Food Coop member proud, including three kombuchas on tap. Bring your growlers.

Best Food Close to Ski Catamount

Crossroads Restaurant food plates

CrossRoads restaurant, tucked behind the Hillsdale General Store on Hillsdale’s Main Street, reminded us of Saltie in Brooklyn. A simple menu of soups, salads and sandwiches is packed with so many creative ingredients, it’s tempting to order everything. It’s modest tagline reads “Hudson Valley farm-to-table dining, great coffee.” Plus, it’s just a few miles from Catamount, so you can skip lunch in the mountain cafeteria, enjoy it at Crossroads and still get back for afternoon skiing before the lifts close. We fell in love with the salt cod hash and eggs, the smoked Long Island fluke sandwich, the escarole soup and perfect little doughnuts.

Best Beer Close to Ski Catamount

Troegs beer at Crossroads

This one also goes to CrossRoads restaurant, which features a half dozen rotating pours from Northeast breweries including, on the day we were there, Perpetual IPA from Troegs and several from Berkshire Brewing Company.

Best Restaurant #1


For a little town, Great Barrington has a wealth of eating options, from the popular sourdough pizza joint Baba Louie’s to the hippie-clad Gypsy Joint that features burgers, sandwiches and live music nightly. For memorable meals and late-night socializing, we gravitated to two places. One is Allium, a cozy, welcoming spot that was a pioneer restaurant in featuring Berkshire-grown, and whose deviled eggs and bacon jam, beet salad, fish tacos, steamed buns, beans and vegetable ragout and local meat many ways are binge worthy. There’s also plenty of brown booze on their cocktail list if bourbon and sazerac are your thing.

Best Restaurant #2

Peter Barett shot of Prairie Whale

On the other side of Main Street from Allium is a beautiful, blue building that, around the New Year, posted a “Jedi Eat Here” sign above the sidewalk. This is the Prairie Whale, opened by Mark Firth, who before moving with his family to a farm in the Berkshires, was co-owner of living-legend Brooklyn restaurants Diner, Marlow and Sons and others with Andrew Tarlow. These chops show in the food and drinks at Prairie Whale (a 19th century Midwestern term for “pigs”). Even better, Firth raises the praised porcine parts himself.

Best Coffee Roaster

No. Six Depot image

The tiny town of West Stockbridge barely has a Main Street. But it does have a train line running through it and a coffee roaster just beside the tracks with a gleaming, well-tuned Victoria Arduino espresso machine that pours out great coffee. No. Six Depot also serves food, and it’s sometimes open late, including the nights when it hosts Berkshire ska bands, folk singers and other live shows.

Best Cheesemonger and Mobile Office Spot

Rubiner's stack of cheese

The first time we visited Rubiner’s, Great Barrington’s cathedral to cheese in a renovated bank building, we imagined there is an underground tunnel between Brooklyn and Great Barrington. There was Mast Brothers chocolate, Tumbador ring-dings and McClure’s Pickles. But also bread and cured meat from Fish & Game in nearby Hudson, eggs from five local farms and a fish club. And there’s even more! Behind this shop is Rubi’s Cafe, an espresso bar that serves excellent food all day, including oysters at night. The tables are flat enough and the wifi strong enough to make this our favored mobile office in town.

Best Sweet Snack

Mighty Brittle

Small-batch food entrepreneurship is alive and well in the farm-rich Berkshires with more local-made pickle, granola and grass-fed yogurt options than most larger communities. Among the new favorites, we spotted at No. Six Depot is Mighty Brittle, a perfect pick-me-up for the slope, or just as good apres-ski. Made by New Lebanon-based For the Love of Pi Foods, which also sells at Smorgasburg, Mighty Brittle just released its espresso-flavor, co-created with No. Six.

Best Ice Cream Shop


With its factory right in Great Barrington, this “South County” creamery makes micro-batched ice cream in a dizzying list of flavors, including Banana Brownie, Berkshire Berry and PB Mudslide. Even when it’s cold outside, the Main Street SoCo Creamery shop is steamy with customers sipping hot chocolate and munching ice cream sandwiches.

Best Booze

BMD product-cornwhiskey

A wee seven years old, Berkshire Mountain Distillers is already turning out a full liquor cabinet of hootch, from vodka and gin to the Manhattan-friendly Berkshire Bourbon and its latest creation, a New England Corn Whiskey. Look for them on drinks menus or ask for your favorite cocktail with something from BMD.

Best Cure-all

Image of Fire Cider courtesy of Fire Cider

Part home remedy, part hipster hangover helper, Fire Cider is an amazing tonic of apple cider vinegar, lemon, garlic, habanero pepper and other active ingredients that will open up your sinuses, unclog your ears and ward off illness. Although Fire Cider’s makers deliver a tongue-in-cheek disclaimer (see this video) that these health claims have not been evaluated by the FDA (or or anyone else), I will attest to its cure-all properties. Each bottle comes with a graduated shot glass with levels for “common cold,” “hangover,” and “wolf attack.”