Fall Drinks

Drink in the Season with the Finest Fall Offerings in The Fenway 


As we head into the fall wrapped in sweaters and clad in boots, it’s clear that more is changing than just the weather. With the cooler weather comes a change in wardrobe, a change in mood—and a change in what’s in our glass. As the leaves turn brown, so does the liquor we tend to associate with the season. Whiskey seems to reign supreme once again as the light, bright, sweet and fruity drinks of the summer are replaced by denser cocktails characterized by autumnal spices, seasonal infusions and creative uses of herbaceous amari. And don’t be surprised to find an increased use of cranberries, apples and pumpkins—all the things that make seasonal concoctions unique.

So here are a few our favorite new fall drinks, as recommended by The Fenway’s most skilled craftsmen. Whether up, down, shaken or stirred, you’re sure to find a sippable tipple perfect for the season.

Sweet Cheeks 
The O.G. Brexit Cup
As creator/bartender Moe Isaza explains, “America was the first ‘Brexit’ and cranberries are a defining crop from where [the Pilgrims] landed.” An elevated take on the Pimm’s Cup, Moe’s creation combines Pimm’s, house-infused cranberry gin, cranberry shrub and Peychaud’s bitters, shaken with cucumbers, served over ice, topped with soda water and garnished with fresh cranberries and a mint sprig in a big ‘ole Mason jar. More potent and more effervescent than a traditional Pimm’s Cup, the cranberry concoction is a great drinkable link to take you from Indian summer to fall.

Strength of a Bear and Girl From Munich 
Bartender Devo Burroughs brings us a sneak peek of two stellar cocktails about to hit the menu at Audubon. The Strength of a Bear brings us an even more autumnal take on the New Orleans classic, Vieux Carré. The updated version calls for equal parts Pierre Ferrand Cognac, Old Overholt Rye, a bit of Benedictine and adds a subtle detour of a house barrel-aged combination of Old Monk and Plantation Overproof Rums, stirred and strained into a coupe with orange zest and peel.

Taking it one step further into the depths of autumn, Devo recommends the Girl From Munich. Combining Pierre Ferrand Cognac with the Amaro Ramazotti, Old Overholt, a house-made red wine syrup (equal parts Chianti and brown sugar) stirred and served in a coupe with orange zest and an included swath. It may not contain any German ingredients but, as Devo states, the drink is a tribute to a German friend who “picks you up when you’re down and is there with you when you’re feeling high.” It’s a drink for both the good and bad times!

Relaxing Times Highball 
As head bartender Daren Swisher notes, the Relaxing Times Highball is named in tribute to Bill Murray’s Suntory Whisky ad in Lost in Translation. A summer cocktail bearing the same name was recently used at Hojoko, but while the name lives on, the ingredients have changed. Combining Suntory’s Toki Japanese Whisky with Bragg’s organic, unfiltered apple cider vinegar, local wildflower honey from Carlisle, Massachusetts and Angostura bitters, the drink is served over ice and topped with Saratoga Springs sparkling water. Whisky-forward, the refreshing beverage is relaxed with its inclusion of vinegar and soda.

Eastern Standard 
Spanish Lady 
Setting the standard in the country’s cocktail community, Eastern Standard’s recently redesigned drink menu contains major changes that suit the season. For a lovely transition into the fall, try the Spanish Lady. Described on paper as “Our herbaceous offering” with “mysteriously original rum,” the drink contains equal parts of Trinidadian Angostura 7-year rum matured in used bourbon casks, Amaro Montenegro, Benedictine and fresh lemon juice with a few dashes of Angostura bitters. Shaken and served up, the drink features bright orange flavors mellowed with subtle fall spices. And if you want the straight stuff, Eastern Standard is also offering pours of Daron Calvados, Marie Duffau 15-year Armagnac and Armorik Single Malt Scotch. Each can be enjoyed on their own or in a flight of three. 

The Hawthorne 
Lockless Door 
Just a few doors down from Eastern Standard, you’ll find The Hawthorne—but only if you look really hard. It’s like walking into a subterranean high-class living room and when it comes to a fall libation, bartender MacKenzie Cavanagh immediately recommends the Lockless Door. A high-brow, off-menu take on the Sidecar, the Lockless Door is named after the Robert Frost poem of the same name. Combining Pierre Ferrand 1840 cognac with a cinnamon- and black pepper-infused orange liqueur, Amaro Nonino, fresh lemon juice, a touch of maple syrup and Angostura bitters, the cocktail is shaken, strained and served in a coupe. Packing autumnal spices, citrus and subtle sweetness in a singular cocktail, the creation is perfectly balanced and perfect for sweater season.

Island Creek Oyster Bar 
Shelburne Spritz and The Spanish Armada 
And, just a few more doors down, you’ll find Island Creek Oyster Bar (a.k.a ICOB), known for its fresh, regional seafood. The drinks here are also crafted by the same people who keep Eastern Standard and The Hawthorne at the top of their game. This fall, bartenders at ICOB are recommending the Shelburne Spritz. Named after the local apple orchard in Stow, Massachusetts, the libation combines a pear and fall spice-infused vodka combined with local honey, fresh lemon juice and a splash of Cava. Or if you want a true Kenmore classic, ICOB welcomes the return of legendary mixmaster Jackson Cannon’s The Spanish Armada, which combines Cognac, sherry, Licor 43 and bitters.

Tiger Mama 
Beverage Director Charles Coykendall and bartender Schuyler Hunton have recently introduced the Autumnatic to their fall menu. “It instantly conjures up the fall season,” says Coykendall. Mixing 1.5 ounces of St. George Terroir gin, half an ounce of Bols Genever, half an ounce of housemade cranberry syrup, half an ounce of Alessio Torino Vermouth, a dash of Fee Brothers Barrel-Aged Bitters, the drink is stirred and strained into a chilled coupe and rinsed with a peaty Islay Scotch, orange oil and garnished with a leaf of sage.

Citizen’s Public House
Flight of the Buffalo 
“I wanted to use fewer ingredients and make a spirit-forward drink using one of my favorite spirits, Buffalo Trace,” says Citizen bartender, Rich Fiorillo. Combining his favorite whiskey with fresh-pressed apple juice made with apple with skins on, Moroccan vanilla syrup and Angostura bitters, this drink is shaken, and served up in a coupe. Whiskey dominated with subtle touches of fall flavors, this drink keeps the brown liquor as the focus with a nod to the approaching season.

Loretta’s Last Call 
Fall Sangria 
Swing by Loretta’s for music and a taste of the South. Restocking last year’s popular Fall Sangria, the bartenders at Loretta are slinging oranges, cinnamon sticks and apples steeped in red wine and topped off with ginger beer.

Boston Beer Works
Pumpkin Works, Oktoberfest and Pumpkin Caffe Noir 
Speaking of beer, Boston Beer Works have been doing what they do best since 1992 and remains one of the largest producing brew pubs in the United States. Brewing many of their offerings onsite, Boston Beer Works’ Fenway location has just released three fall classics: Pumpkin Works, Oktoberfest and Pumpkin Caffe Noir. Pumpkin Works is a bright mahogany color and loaded with cinnamon, nutmeg and malt with a 5% ABV. Their Oktoberfest is a traditional Märzen lager with a copper color, German hops and malt, and promises to be rich and hearty with a 6% ABV. Rounding out the list, the Pumpkin Caffe Noir is a spiced coffee stout in a brazen, deep obsidian color, roasted flavors with nutmeg and vanilla coming in at 5.5% ABV.

So, what is your favorite fall drink in The Fenway?











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