The Berkshires in western Massachusetts may be better known for their gourmet and farm-to-table dining options, but what has been shifting over the past few years—and really gaining momentum—is the cocktail culture.

Where to drink craft cocktails in the Berkshires 

Whether you’re looking for a spot that does the classics well or looking for cocktail housemaid infusions, there are options from Williamstown to the Connecticut border of the region. I’ve included a list of some of my favorite places (and it’s a long one) to get a craft cocktail in the Berkshires of western Massachusetts. 

Mezze Bistro + Bar, Williamstown

Located in northern Berkshire County, Mezze has had a proud tradition of locally sourced meals and impeccable service since Nancy Thomas opened the restaurant in 1996. This philosophy also rings true for their beverage program. Usually, on or ahead of the curve and cocktail trends, Mezze Bistro is a great spot for a formal date night or a night out with friends. 

Drink: Bootsy Collins with pineapple vodka, Lillet rouge, lemon, and soda or the False Start gin, grapefruit, honey, and celery bitters

The Airport Rooms at Tourists Welcome, North Adams

The newest outpost of the hit tourists welcome motel; the airport rooms remind me of the place to see and be seen. Remodeled from a former boarding house, The Airport Rooms still feels like you’re in someone’s very cool upstate home. The bar, but its retro vibe, offers a short cocktail menu that matches the cool environment.

Drink: Grab any of their perfectly crafted beverages and then settle into some live music or for dinner from one of the hip restaurants stopping in for a pop-up!

District Kitchen & Bar, Pittsfield

I recently had the opportunity to stop by District after they remodeled, and love the new look. I was especially impressed by the cocktail program, which features drinks like XYNZ. Special shout out to bartenders Cody and Amanda for giving me a lead on a couple of other great spots to drink

Drink: Lookin’ Pine: House-infused ginger vodka, Zirbenx pine liqueur, Creme de cassis, lemon, rosemary syrup, prosecco or Should I Get Bangs? Casamigos Reposado tequila, Patron Citronge, grapefruit juice, lime, spiced vanilla syrup, nutmeg 

Public Eat & Drink, North Adams

The sister restaurant to District in Pittsfield, Public Eat and Drink, has been serving new American cuisine since 2011 and is worth a stop with up in North Adams after a visit to MASS MoCA or for any reason you are in northern Berkshire County. 

Drink: Tea Time with Organic Bangkok tea-infused gin, Chinese five-spice simple syrup, lemon or Feel the Heat with Hanson’s Organic habanero vodka, Creme de Cassis, lemon, simple syrup, TNT Bitters Co. and Kamikaze bitters. 

Methuselah Bar & Lounge, Pittsfield

On what has been referred to affectionately as “Upper North” street in downtown Pittsfield, Yuki Cohen has been upping Pittsfield’s craft cocktail game since she opened her hopping little bar in 2015. Methuselah’s cocktail menu includes a mix of classic and contemporary, many including house-made spirits. 

Drink: Yellow Cloak Club with Del Maguey VIDA Mezcal, Yellow Chartreuse, Benédictine, Orange + Ginger Syrup, and Lemon Twist or one of my personal favorites, Tea Time with Rosa with Cocchi Americano Rosa, Earl Grey Syrup, Grapefruit Juice, and Sparkling Rosé. 

Prairie Whale, Great Barrington

The team at Prairie Whale has been crushing it in the kitchen since they opened in 2012, but have you had a drink at the bar? The Prairie Whale, which was recently featured in Bon Appétit’s list of “24 restaurants we couldn’t stop talking about in 2019,” has a cozy wooden bar and beverage program to match the constantly rotating farm-to-table menu. 

Drink: Like in true farm-to-table fashion, the prairie whale changes their menu daily to reflect the seasons; stop in for brunch and grab one of its Bloody Marys. 

Cantina 229, New Marlborough

Located on the outer edges of the Berkshire Hills, Cantina 229 in New Marlborough. While their Taco Tuesday is what originally brought me there, their Mezcal Mondays are an industry family secret that more folks should be driving to to enjoy. 

Drink: Cantina Mezcal Negroni: leyenda mezcal oaxaca, campari, caprano antica vermouth, zucca rabarbaro or ...Thats What she Said: leyenda mezcal guerrero, aveze gentian liqueur, honey jack syrup, strawberry infused dolin blanc

Mooncloud, Great Barrington

This sister restaurant to Cantina 229, Mooncloud is the newest on our list and also the craft cocktail space and salumi bar we needed in the Berkshires. Josh Irwin and Lorenzo “Ren” Price, the chef de cuisine at Cantina 229 are behind the venture and I’m pumped to see this spot and more thoughtfully crafted cocktails in the region.

Drink: The Butterfly Effect with BMD Ethereal gin, Mill River honey, lemon, strawberry, Aveze or Gunpowder & Treason with Plymouth gin, Cardamaro, Lagavulin 16yr., burnt orange oil

Alpamayo Restaurant, Lee

I’ll admit that this is one of my favorite spots on the list. After spending time with Javier and his wife when writing my piece on Alpamayo Restaurant for The Berkshire Eagle, I learned that Javier had been an accomplished mixologist in Peru and was introduced to a world of pisco-based cocktails! 

Drink: Maracuya Sour, made with Pisco, passion fruit, lime juice, egg white and jarabe de goma, or the Chilcano de Pisco with Pisco, lime juice, Angostura and ginger ale. 

The Widow Bingham’s Tavern and The Front Porch at The Red Lion Inn, Stockbridge, Mass

I can’t leave this Berkshire staple off the list for two key reasons: their iconic Bloody Mary (made from scratch and not from a mix) and the perfect Berkshire moment of having a beverage on the front porch in the summer, or by the cozy fireplace in the winter.  At The Red Lion Inn, who knows, you might see a celebrity, former president and famous dignitary in the next chair over. 

Drink: Grand Manhattan: Grand Marnier, BMD Bourbon, Sweet Vermouth, Angostura Bitters

Shire Breu Hous, Dalton

Shire Breu-Hous is a 7-barrel brewpub located on the grounds of The Stationary Factory in Dalton, and while they are known for their wild fermentation-style beer, their cocktails are on point as well. Visit the brewery and restaurant downstairs in the basement of the historic building once owned by Crane Stationery, and grab a pint or one of their craft cocktail selections, many made with local ingredients.  

Drink: The Red Door Bulleit Bourbon with Antica sweet vermouth, Silver Bear Maple Liqueur, fresh lemon & lime & candied Maraschino cherry

The Stagecoach Tavern, South Egremont

Located in Southern Berkshire county in the village of South Egremont, Stagecoach Tavern is the restaurant and bar part of the Race Brook Lodge. A beautiful, rustic setting with a locally inspired menu, their beverage program features not only a selection of innovative rotating in-house cocktails but a cocktail bucket list of “50 class cocktails to try before you die”. MixologistRafa Russi-Catalan seems to be doing some exciting things in south county and a visit to Stagecoach Tavern definitely should be on your list. 

Drink: Love Me Tender with Serrano pepper infused bourbon, Cynar, amontillado sherry, mulled cider, lemon, maple syrup, Himalayan salt, or Queen of the Islay with blended Scotch, Laphroaig single malt, simple syrup, lime, mint, absinthe rinse

Got Recommendations?

As with all my lists and roundups, this is only a starting point! I’m sure there are places I’ve missed, but I wanted to give you a head start when traveling (or living in the Berkshires) and to want to drink well. 

Places come and go or are open seasonally to keep an eye out for any schedule changes or availability for each restaurant. As with the changing seasons, cocktail menus change as well, so the ones that are listed here are examples that they have had at one point it may not be on the menu at this time. 

Is there a place with a killer craft or classic cocktail in The Berkshires or in western Mass that you think should be on my radar? Comment below, I'm excited to check them out.