Your Perfect Guide to the Berkshires: Where to Stay and What to See

Prairie Whale, Great Barrington, MA

In 2012, Brooklyn restaurateur Mark Firth (of Diner and Marlow & Sons) brought his signature elevated rustic cuisine to the Berkshires. Prairie Whales' menu changes daily, but diners will find farm-to-table dishes like pork chop with savoy cabbage, roast potatoes, rosemary, and calabrese pepper, and braised rabbit leg with bacon, duck fat potatoes, and sauerkraut.

Eat on North, Pittsfield, MA

Chef Ron Reda might have crafted a casual, delightfully-unfussy menu for Eat on North, but he cut his teeth in one of America’s most demanding kitchens: The White House. Now, the Pittsfield native serves up grass-fed burgers and New England style fish and chips (sourcing ingredients from MA, VT, and the Hudson Valley) in a cavernous, light-filled dining room that calls Hotel on North home.

Cantina 229, New Marlborough, MA

Venture 15-minutes out of Great Barrington to more rural New Marlborough and you’ll be rewarded with a meal at one of the Berkshires’ best restaurants. Cantina 229—the passion project of husband-and-wife duo Josh Irwin and Emily Rachel—brings to the table an internationally-inspired menu crafted from locally sourced ingredients. Hang around in the airy, four season dining room to get a look at how your bibimbap and tostones are prepped in the open concept kitchen, but post-meal, head outdoors for lawn games and a bonfire.

No. Six Depot, West Stockbridge, MA

Itchin’ for a caffeine fix in West Stockbridge? This rustic small-batch coffee roaster/cafe/art gallery is our go-to. They also happen to serve up a mean panini; go for the porchetta with truffle aioli, hazelnut gremolata, and lemon-caper aioli and get ready to make a few new friends—the cafe's long, communal tables encourage rubbing elbows with neighbors.

The Briarcliff Motel, Great Barrington, MA

With retro rooms, a lodge-like lobby, and a sweet location—in the shadow of Monument Mountain—the Briarcliff proves that modernday motels can exceed their divey, 60s-era reputation. A study in primary colors (the exterior is duck-egg blue) and personality-filled petite spaces, the 16-room B&B is as IG-friendly they come.

Hotel on North, Pittsfield, MA

At Hotel on North, a 45-room boutique that was once an 1880s department store, no two rooms are alike. Furnished with tables, mirrors, and cabinets plucked from local vintage shops and estate auctions, each reserves its own take on New England charm. Before you checkout, be sure to sip a cocktail in the hotel’s birdcage-elevator-turned-bar, and grab a bite at Eat on North, the onsite New American restaurant helmed by an ex-White House chef.

Porches Inn, North Adams, MA

Just steps from the Massachusetts Museum of Contemporary Art (MASS MoCA), a series of restored 1890s row houses comprise Porches Inn. Simultaneously retro, industrial, edgy, and chic, the 47-room property is awash in New England knickknacks and funky furnishings, but also features major hotel amenities like a heated pool and fitness center.

Wheatleigh, Lenox, MA

Built in 1893, the 16th-century, Florentine palazzo-style Wheatleigh was once the summer cottage of a Count and Countess. Now, rather than hosting Gilded Age parties, the 380-acre estate welcomes guests with cushy rooms, a wine cellar, and an eponymous park designed by Frederick Law Olmstead—the very dude behind NYC’s Central Park.

Tunnel Bar, Northampton, MA

Oversized martinis—nearly 30 different varieties—are the calling card of this Northampton bar. In a previous life, the circa-1896 space functioned as a Union Station train tunnel; today, patrons may travel there for drinks, not rides, but the spot is every bit as atmospheric thanks to original stone and brickwork.

PUBLIC eat & drink, North Adams, MA

Industrial charm and an extensive rotating craft beer program lure visitors out this northern Berkshires bar and restaurant. Tucked away in North Adams, an old mill town that’s undergone something of a renaissance in recent years (see: MASS MoCA), PUBLIC is a go-to for casual meals and tasty cocktails.

The Lion's Den, Stockbridge, MA

Mosey into The Red Lion Inn on Main Street in quiet Stockbridge, and you’ll find this cozy pub holing up just downstairs. The intimate bar has live entertainment every night of the week, pints of ale, mugs of mulled cider, and a toasty open fireplace.

Mohawk Trail Scenic Drive, Athol to Williamstown, MA

Running roughly 69 miles from Athol to Williamstown, Massachusetts, the Mohawk is a leaf peeper's dream. Taking Routes 2 and 2A, foliage fiends follow the trail as it runs parallel to the Deerfield River and over the Connecticut River, with astounding views of the Berkshires and Taconic Mountains all the while. Drive cautiously as you might run into a bobcat or black bear, but what's most dangerous is the trail's infamous hairpin turn—Dead Man's Curve.

Dory & Ginger, Pittsfield, MA

Looking for a Berkshires memento but not your stereotypical souvenir or tchotchke? Head to Dory & Ginger in Pittsfield (right next to Hotel on North) for homewares, jewelry, prints, clothes and stellar conversation with shop owners Cara (Ginger) and Laurie (Dory).

Tanglewood, Lenox, MA

More than 350,000 visitors flock to Tanglewood every year. Though the outdoor Lenox and Stockbridge venue is known for being the summer home of the Boston Symphony Orchestra, popular artists like Tony Bennett and James Taylor also drop in for performances. Even if you stop by post-concert season, you’ll find beautiful views of the Stockbridge Bowl.

Massachusetts Museum of Contemporary Art, North Adams, MA

Large-scale, immersive installations take precedence in MASS MoCA’s 250,000-square-foot converted factory building campus in North Adams. With innovative works from established and up-and-coming artists, more than 75 annual performances (think: contemporary dance, outdoor silent films with live music, and avant-garde theater), and hands-on educational programs for all ages, the museum is one the States’ finest.

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