From Bourbon, Beer & Angostura Bitters, Sip the Best of Boston’s Cocktails


eastern standard

Eastern Standard

“I enjoy bourbon. Nothing too sweet. And flavors that are sour and spicy.”

I love venues like this. Mike and I are exploring Boston’s nightlife, starting with the Eastern Standard. The dim restaurant and bar is littered with high-top tables and soft candlelight, giving the allure of romance. While we love the elegant yet cozy ambiance, we are here for one reason: classic cocktails.

There is a parchment paper menu in front of me, but instead of browsing it I tell the waitress what flavors I like so she can recommend something special. She brings me a Lion’s Tail, a mix of bourbon, lime juice, pimento drams, gomme syrup and Angostura Bitters, with the ingredients being mixed and double strained into a chilled cocktail glass. The bartender has crafted these cocktails with the precision of a scientist, and the flavors compliment each other strikingly well.

Mike orders a Manhattan, his go-to drink of choice no matter what bar we go to; however, his reaction to the mix of sweet vermouth, bourbon whiskey and Angostura bitters tells me it’s as if he’s having the libation for the first time.

We sip slowly, wanting to savor every moment of the drinks. I can’t believe these cocktails are only $10, as I would have paid triple that to enjoy something so well-crafted. The Bar Manager, Jackson Cannon, comes over to our table to chat with us. I had interviewed him a few months ago for a piece on classic cocktails, and he wanted to thank me and show me around.

“Have you seen Island Creek Oyster Bar or The Hawthorne yet?” he asks.

I’m unsure what he’s referring to. “No. Are those nearby?”

He smiles. Apparently, they are more than nearby. They are in the same building, The Hotel Commonwealth, where Jackson influences all three cocktail venues. And so, our night of classic cocktails in Boston continues.

island creek

Island Creek Oyster Bar

Is it possible for an upscale bar to moonlight as an oyster farm? At Island Creek Oyster Bar, I’m astounded at how they’ve managed to bring farm elements into this space and make it look pristine. Moreover, I’m a bit taken aback by the quick change from dimly lit romance to glitzy white interiors. Gabion cages filled with tens of thousands of oyster shells makeup the three-dimensional walls, while reclaimed Wyoming snow fence is used to create the shutters and wood from a restored Vermont farmhouse has been refurbished to build the wainscoting. Even when perusing a menu you’ll notice the names of small farms carefully listed next to each dish, each specializing in farming freshwater and marine plants and animals.

While Eastern Standard breathes life into pre-Prohibition cocktails and creates new cocktails, Island Creek focuses on quality cocktails with a local and seasonal twist. Although I know we have another stop after this one, I can’t help but order something just to sample, and Mike follows my lead. I opt for a mixture of crushed lime, Rich Demerara syrup and ICOB’s house 4 Rum called the “Snug Harbor Mash,”while Mike is well-behaved and samples an “ICOB Pilsner,” an exclusive pilsner brewed with jasmine and orange peel.

We take our drinks to the center of the restaurant, where our eyes settle on a stunning 38’ x 18’ photograph of Duxbury Bay at low tide, brought to life by artist Stephen Sheffield. Wanting to get to know the specialties of the venue a bit better, Mike and I order a plate of crispy oyster sliders with lime chile aioli and a helping of Steamed Duxbury Littlenecks with ICOB slab bacon, rosemary fennel broth and scallion butter. I’m seamlessly immersed in local aquaculture, while still being able to wear a clean party dress.

We finish only half our drinks, but all our food, as we know we still have on more stop on our classic cocktail’s in Boston crawl.

the hawthorne

The Hawthorne

Next, we move on to Jackson’s newest project, The Hawthorne. Here, the focus is truly on the bar and craft cocktails, with an expansive cocktail menu filled with nouveau classics, rediscovered favorites and rotating creations. Because the bar is technically a hotel bar, the idea is to bring some of the homey, residential feel into design of The Hawthorne. Jackson shows Mike and I around. It’s comfortable yet sophisticated, with an upscale urban apartment theme. In one area, a group of imbibers relaxes on a loveseat and plush chairs, surrounded by works by artists like Stephen Sheffield and glass coffee tables.

As we walk into a separate room off the bar, the background noise seems to go completely silent, and the ambiance softens. Tall bookcases and a globe sit next to a mix of nude, orange and zebra print chairs. Look closer at one of the bookcases, and you’ll notice it’s not just books in there, but some of Jackson’s favorite things, like his favorite spirits line and personal glassware. A simple rolling cart is setup in this quieter room, and Jackson shows us just how much they can do with a few feet of space and some drawers.

“Ready for some cocktails?” Jackson asks, taking us to meet Head Bartender Nicole Lebedevitch. I would actually pay money to sit and watch her make drinks. It’s as mesmerizing as a Broadway show. Except, there’s no acting here. Nicole seems to know everything there is about classic cocktails and making quality drinks, as she muddles, pinches and mixes hard-to-find spirits and ingredients, using about 20 different instruments to accurately pour each shot of liquor.

Once we are seated at the bar with our liquid masterpieces, Mike turns to Jackson. “So, do you have a favorite on the menu?”

Jackson looks perplexed, and we’re not sure if he heard the question. He turns to the bartender for help, but she just shrugs and laughs.

“Sorry, I’m not trying to be difficult,” explains Jackson. “It’s just that there is a time and place for each cocktail. It depends on what you’re eating, what your mood is. There are many factors that come into play.”

I must have been in the right mood at the right time, because my “Scarlett,” a mix of Russian Standard, berries, lime and ginger, is perfect. The ginger is the best part, spicy but not overwhelming. Mike seems to be enjoying his usual “Manhattan,” the rye whiskey, sweet vermouth and Angostura bitters flawlessly strained and served in a rock glass.

As we sip, I think of how nice it is to indulge in a quality drink, instead of chugging the cheapest wine a place has (guilty as charged). It takes us an hour and a half to finish our drinks, as we savor every sip, not wanting to the magic happening on our taste buds to end. When we are done, we thank Nicole and Jackson, and head for the door. I’m not drunk at all, just relaxed and happy, like a good cocktail should make you feel.

“Excuse me miss, you forgot your coat,” a gentleman in a black suit calls from the bar.

I guess a few classic cocktails can make me tipsier than I thought.

Top Image via Eastern Standard

Jessica Festa
Jessica Festa is the editor of the travel sites Jessie on a Journey ( and Epicure & Culture ( Along with blogging at We Blog The World, her byline has appeared in publications like Huffington Post, Gadling, Fodor's, Travel + Escape, Matador, Viator, The Culture-Ist and many others. After getting her BA/MA in Communication from the State University of New York at Albany, she realized she wasn't really to stop backpacking and made travel her full time job. Some of her most memorable experiences include studying abroad in Sydney, teaching English in Thailand, doing orphanage work in Ghana, hiking her way through South America and traveling solo through Europe. She has a passion for backpacking, adventure, hiking, wine and getting off the beaten path.
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