TAKE A DEEP DIVE

THE BERKSHIRES BARS YOU NEED TO TRY TONIGHT

By Taylor Staubach

Photos by Gregory Cherin

July2026

Read Berkshire Magazine's August 2026 Issue.

THE BERKSHIRES IS SMALL ENOUGH that you’re almost guaranteed to bump into someone you know at Guido’s, the bank, or the weekend farmers market. But there’s a big difference between exchanging pleasantries at the deli counter and bellying up to a bar where its tender already has your drink started. Those spots can feel sacred. They’re the places you go after a tough day, to meet your “non-small talk” friends, or just enjoy a meal you didn’t eat under the glow of a TV screen. Call them dive bars if you want—Guy Fieri did and Yelp ranked three of these spots among Massachusetts best dives in recent years—but really, they’re places where the pressure is off. There’s no need to impress anyone or dress up, and you already know your way around the room, or you will in short order. Sometimes all you need is a cold draft, a corner that hasn’t changed since the ’90s, and really good bar pizza. At the end of the day, these places remind us that a great bar doesn’t need to be fancy. It just needs to be a room full of neighbors, something to wet your whistle and a place where you can kick back and feel at ease.

KEY WEST LOUNGE

Take the Key West Lounge in North Adams. The bar celebrates its 40th anniversary this year. It’s a straight- forward, welcoming lounge where the atmosphere remains relaxed. Expect no-fuss bar food until midnight, along with pool and jukebox tunes until closing. Key West has been consistently named one of the top dive bars in Western Massachusetts by Yelp.

159 State St., North Adams, on Facebook

ZINKY’S

A bit more South in Dalton, Zinky’s Pub keeps hometown traditions alive. Formerly know as Jacob’s Restaurant before changing ownership in 2021, it’s younger than some of the old guards, but it quickly stepped right into the role of the neighborhood sports hangout. The walls are covered in local high school sports memorabilia, and they’ve got 12 TVs running everything from big games to daytime horse racing, paired with

hearty pub food and weekly live music.

51 Daly Ave., Dalton, zinkyspub.com

EAST SIDE CAFE

Pittsfield is home to some serious tavern history, boasting establishments that have anchored neighborhoods for generations. The East Side Cafe on Newell Street has been open since 1933, making it the oldest continuous bar in the city. Famous for its coal-fired pizza (the only one in the Berks!), the café expands its traditions during the summer and fall with pasta on Wednesday nights and tapas on Thursdays, including charcuterie boards and bruschetta, in addition to their famous pies.

378 Newell St., Pittsfield, on Facebook

CIM’S TAVERN

Not far away on Fenn Street, Cim’s Tavern has been doing its thing for over 40 years. Another Yelp favorite, Cim’s has been owned by Rick Cimini and his brother since 1985, and it remains a classic sports pub: reliable taps, bar games, and a kitchen turning out legendary brandy- glazed wings that locals swear by.429 Fenn St., Pittsfield cimstavern.wixsite.com/pittsfield

O’LAUGHLIN’S PUB

If you want a taste of old-school industrial in the heart of the city, O’Laughlin’s Pub on Merrill Road isa total neighborhood joint that dates back to the booming days of GE. It’s the kind of place where you can grab a great burger or sandwich without any fuss, though it gets packed on Friday nights for the prime rib dinner, and again

on Saturdays for the leftover prime rib sandwiches. Sundays are for classic rock bands playing live.Merrill Rd., Pittsfield, on Facebook

SHAW POND CLUB

For something you truly won’t find anywhere else, you have to head out to Becket to Shaw Pond Club. Operating under a club license since the 1960s, it functions much like a VFW—you can walk right in as a guest, or you can pay $20 a year to officially join. Inside, you’ll find a jukebox, dartboards, a ping pong table, and a crowd-favorite arcade mini golf game. They even have one TV that plays nothing but the Bob Ross channel 24/7. The food leans heavily into comfort: Burgers are made with fresh ground beef from Mazzeo’s, the fries are cooked in beef tallow, and the BLT has a local reputation. In the summer, you can hear the clink of horseshoes out back from a league that’s been throwing there for four decades. 4494 Otis Rd., Becket, on Facebook

LISTON’S BAR & RESTAURANT

Up in the higher country of Worthington, Liston’s Bar & Restaurant sits at 1,776 feet of elevation, making it the highest bar in Massachusetts. The Worthington Restaurant Group bought and completely rebuilt it in 2022 to save a historic hometown landmark from disrepair while preserving its character. They even put a massive photograph of the old “legendary” pre-renovation bathroom inside the new bathroom as a joke. Outside, the patio has incredible views of the sunset and fall foliage, and they pour a custom Liston’s Moose Ale brewed for them by Sam Adams.

324 Old North Rd., Worthington listonsbar.com

BUCKY’S TAVERN

Down in Lee, you’ll find two totally different takes on the neighborhood tavern. Bucky’s Tavern keeps things simple and friendly, serving reliable lunches and dinners six days a week. Opened in a former laundromat nearly 25 years ago, Bucky’s added an outdoor patio in 2021 and pours ten traditional draft offerings. 25 Consolati Way, Lee, on Facebook

MOE’S

Nearby, Moe’s Tavern caters to the craft beer and whiskey crowd. The bar has since expanded to include a full bar and plenty of non-beer options. Yelp has named it one of Massachusetts’ top dive bars. Its website, nocoorslight.com, tells you plenty about its approach to beer, though the staff will happily serve a Coors Light if you ask. Moe’s hosts a monthly open mic night, occasional live music, and what it claims are the best bathrooms around—we’ll let you stop in and be the judge. Open 363 days a year (closed Thanksgiving and Christmas), it’s a lively spot with a constantly rotating tap list.

10 Railroad St., Lee, nocoorslight.com

BOGIE’S RESTAURANT & PUB

In Great Barrington, things stay casual but take on a different vibe. Bogie’s is built inside a converted barn, and it’s a favorite local choice if you want to shoot some pool or step up to the mic during a karaoke night. 935 Main St., Great Barrington, bogies935.com

THE MILLER

Right downtown on Main Street, The Miller brings a bit of a across-the-pond feel to South County. The Miller was started by four friends who wanted to blend a classic American bar with the open, conversational atmosphere of a British pub. Behind the bar, you’ll often find Biff, a local bartender famous around town for his quick banter. They’ve got 12 taps running a lot of imported UK drafts, plus a frozen drink machine for the summer months. In the true spirit of a community pub, they encourage you to grab takeout from a neighboring spot and eat it in-house.280 Main St., Great Barrington millerspubgb.com