City in a Glass: Boston

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Thirsty? You’re in luck. In Paste’s drinking-and-traveling series, City in a Glass, we mix up a city’s signature swills and slide them down the bar to readers. Grab a stool. This round is on us.



has been an integral part of life for Boston residents since Boston was founded in the 1600s. Back then, gritty New England settlers—including children!—drank distilled spirits instead of water, which was often contaminated with parasites. Today the water is cleaner and the legal drinking age is higher, but the rebellious drinking culture lives on through the city’s notorious Irish pubs and revolutionary cocktail bars such as Drink, a menu-less den in the revitalized Fort Point neighborhood. Want to sip on Boston’s rich past and present? Here are three essential drinks that reinterpret both Beantown and cocktail history, and where to find them. For the purpose of our drinks crawl, we’re sticking to one well-fortified neighborhood: Fenway.

1. Old Ironsides

Where to order: Eastern Standard Kitchen & Drinks

Old Ironsides.jpeg
Photo courtesy Eastern Standard Kitchen & Drinks

Start your evening with a cocktail steeped in American history: Old Ironsides. Old Ironsides is the nickname of the wooden-hulled USS Constitution, the world’s oldest commissioned warship that’s still afloat; it was originally launched in 1797 and is now docked in Boston. Old Ironsides is also the name of a Massachusetts-inspired cocktail at Eastern Standard, one of the foremost cocktail destinations in the city.

Old Ironsides (the cocktail) is made with rum, tarragon, lime juice and cranberry cider. Bar manager Naomi Levy came up with the drink when trying to concoct a beer cocktail—or “beer tail”—using a fruit beer or bubbly cider. She sourced all of the alcohol in the drink from local distilleries and breweries. “I started with Privateer rum because it plays beautifully with fruit and I wanted a nice herbal note to round it out,” she says. A descendant of one of Boston’s first families, the Cabots, founded Privateer rum, which is distilled in Ipswitch, Massachusetts.

“I also wanted to incorporate some ingredients indigenous to New England, which is why I used a cranberry blend cider,” she says. Downeast’s tart cranberry cider is brewed in Charleston, the oldest neighborhood in Boston, which also happens to be where the 203-foot-long USS Constitution is currently docked. “The drink is refreshing first and foremost, with hints of banana, apple and cranberry. It’s rounded out by lime and the herbal and anise notes of tarragon.”

Old Ironsides

1 oz. Privateer Silver Reserve rum
¾ oz. tarragon syrup (instructions below)
¾ oz. lime juice
1 pinch salt
Downeast Cider House Cranberry Blend

Make tarragon syrup: Combine 2 cups of sugar, 1 cup of water and a handful of fresh tarragon sprigs in a saucepan. Heat slowly, stirring until the sugar dissolves. Simmer for 2 minutes. Remove from heat and let cool. Strain.

Make drink: Combine all ingredients (except beer) in a mixing tin with ice. Shake. Strain into a highball glass filled with fresh ice. Top with Downeast Cranberry Blend, creating a layered effect.


2. New Stone Wall

Where to order: Citizen Public House

Applejack—a spirit that dates back to the 1600s in the apple-rich Americas—is made of apple brandy, or distilled apple cider. In the colonial days many settlers didn’t have access to clean drinking water, so they relied on sterile beverages such as beer, cider and concentrated apple brandy (Applejack) for hydration. Rudimentary Applejack gradually fell out of favor as the colonists gained access to non-polluted water and extravagant molasses- and grain-based spirits like rum and whiskey.

New Stone Wall Photo: Courtesy of Citizen Pub

At Citizen Pub, a casual tavern and oyster house on Boylston Street, chef and co-owner Brian Revelt incorporates the classic Americana spirit into a cocktail he calls the New Stone Wall. “It’s a rendition of Dale DeGroff’s Stone Wall,” Revelt says, referring to a recipe by the pioneering bartender behind New York City’s Rainbow Room. DeGroff’s version of the Stone Wall consists of rum, cider, muddled ginger and simple syrup topped with ginger beer. Citizen Pub’s nouveau interpretation is made with Applejack, rum, Amaro Montenegro (an Italian digestif), lime juice and cinnamon. “We wanted to recreate the drink with our twist, using the flavor profiles of cinnamon, lime and Applejack to replicate the ginger and the cider,” Revelt says. The New Stone Wall’s taste is best described as a spiced daiquiri.

New Stone Wall

1 oz. Laird’s Applejack
½ oz. Plantation 3 Stars rum
½ oz. Amaro Montenegro
1/2 oz. lime juice
1/2 oz. cinnamon syrup (instructions below)

Make cinnamon syrup: Combine 2 cups of sugar, 1 cup of water and 4 cinnamon sticks in a saucepan. Heat slowly, stirring until the sugar dissolves. Simmer for 2 minutes. Remove from heat and let cool. Strain.

Make drink: Combine all ingredients in a mixing tin with ice. Shake. Strain into a coupe.


3. “Oooh Mommy” Grasshopper

Where to order: Hojoko

Oooh Mommy Grasshopper.jpeg
Photo courtesy Hojoko

After downing two historically significant cocktails, you need to end your night with something a little more modern and a little more…weird. Daren Swisher and Joe Cammarata, co-bar managers of the Japanese bar Hojoko in the Verb hotel, re-imagine—or “rehab” as they say—vintage drinks that are a few decades old.

One of their most bizarre cocktails is the frozen “Oooh Mommy” Grasshopper. A traditional Grasshopper—a neon green cocktail popular in the 1980s—is made with mint liqueur, chocolate liqueur and cream. At Hojoko, they tweak the recipe and make it with Crème de Cacao (chocolate liqueur), Fernet-Branca (a bitter Italian digestif), Branca Menta (a bitter Italian mint digestif), vanilla ice cream and white miso.

“We try to subtly incorporate Japanese ingredients like sansho, shiitake mushrooms, soy, rice-wine vinegar and sesame into our drinks,” they say. “For the Oooh Mommy, we added some savory umami notes from the white miso and a light bitterness and complexity from the Fernet-Branca and Branca Menta. The salinity from the miso mellows out the bitterness of the two Italian amaris and helps accentuate the mint. It tastes like slightly bitter and savory mint-chocolate ice cream…with a kick.”

Sure, using two kinds of bitters balances out the sweet ingredients, but Swisher and Cammarata admit to having other motives: “We knew that a frozen Fernet-Fernet drink would go over well with our bartender friends.”

“Oooh Mommy” Grasshopper

1 oz. Tempus Fugit Crème de Cacao
1 oz. melted vanilla ice cream 
½ oz. Fernet-Branca
½ oz. Branca Menta
1/8 tsp. mild white miso

Blend all ingredients with ½ cup of crushed ice. Pour into an Irish coffee mug. Garnish with chocolate sprinkles.

City in a Glass columnist Alyson Sheppard writes about travel and hangovers for She currently resides in the great state of Texas.