Photos by Dalton Patton | @daltgetdown
Since my days as an intern, perched atop the giant oak office bar at DigBoston headquarters, I’ve lusted after being assigned a five drink outing. And with a few months of shameless begging, I’m on the ticket. With the warm Somerville night before us, I notice an impressive Halloween lawn display and take this as a good omen. Let’s hope I don’t regret asking for this.
[239 Holland St.]
DRINK 1: TREAT
Kentucky Bourbon Barrel Ale ($7)
The first stop on my spooky path is PJ Ryan’s in Teele Square. My personal goal of the night is to avoid anything pumpkin flavored, so I know I have to strategize, so a Kentucky Bourbon Barrel Ale seems fitting for a drinker’s bar like this. Besides the fancy glassware, this beer tastes–and perhaps is–the bastard child of bourbon and beer. I’m told they do this by having the beer hit the barrel just minutes after the bourbon is drained, which raises the percentage to 8.2%. I’m either off to a great start, or ensuring my utter ruin tonight. Time will tell.
DRINK 2: TRICK
Jalepeno Martini ($10)
I drag my partner and the photog out to Sound Bites in Ball Square. I ask the bartender (who bares a striking resemblance to British actor Steve Coogan) what he suggests for a “trick” drink, and he whips up a fiery vodka martini. I focus on the sweet honey part of the Stoli and the agave notes, as the vodka and jalapeno brine are calling up a long-forgotten memory of the time I made a poor decision while mixing pepper vodka with Coke. We order shots of whiskey as counterbalance, resulting in our Coogan-esque drink slinger take one for himself while buying a round after noticing the pained look on our faces. Call it pity.
THE PAINTED BURRO
[219 Elm St.]
DRINK 3: TWEET
Margarita de la Casa ($9)
My friend Scott spots my desperate tweet and suggests the house margarita at the Painted Burro, a beautiful and vibrant joint where even the light from the beer fridge adds to the endless ambiance. I oblige my Twitter request, and decimate the perfectly mixed margarita before me. This stunner of a place is Instagram gold, but I leave it to my photog haunting every sip I take tonight. Tequila = enduring the 87 bus to the next stop.
TRINA’S STARLITE LOUNGE
[3 Beacon St.]
DRINK 4: WRITER’S CHOICE
Notch Session Pilsner ($5)
Last time I found myself at Trina’s, the bartender reserved our seats by putting vintage bottles of Miller High Life in metal tumblers (with ice) right on the bar, signaling there’s a good range of class and neighborhood flavors afoot. I grab an Honest Pint-approved Notch Session Pilsner for a break from hard booze, while my partner devours Trina’s famous hot dogs. The place is packed due to the Sox game, but we crowd into an quiet corner and chatter about embarrassing tattoos. And hot dogs.
[9 Sanborn Ct.]
DRINK 5: BARTENDER’S CHOICE
Backbar is the place I was most anticipating, but given it’s status as a true tucked-away gem we ask a group huddled next to a door where to go. They point to what seems like an old garage, yet once inside the bartenders are in white shirts and bow ties, missing only old-time-y mustaches and pocket-watches to complete the image. I put my fate into the hands of one, and he serves up a Model-T – their spin on a Manhattan, with bourbon, yellow chartreuse, and Carpano Antica. The glass is rinsed (!) in clove-infused rum, and the whole thing is served, quite appropriately, with a cherry on top. No regrets.