I'm often asked where to go for a great cocktail in Portland, or where I go for drinks. I realize that the answer is increasingly varied depending on the fix I'm after. We thought it would be a good exercise to start cataloging those locations and what to get while you're there. So, to start, Portland Comfort Classics... The places that I've had on my radar for at least a few years for whatever it is they do well. In no particular order:  

Big bowl of booze with sidecar at J's.

1. For Perfect 70's Vibe and a Big Ass Sidecar for my Martini: J's Oyster Bar, Hon.

I wouldn't say that I go there for the oysters, but dang, do I love J's. They're kind of a 'volume operation' when it comes to the raw bivalves, but for a shrimp cocktail, spot at the bar, bartender who calls you 'Hon,' giant Martini with an equally giant sidecar experience that can't be beat, delivered in the location that should have been scouted for Cheers® were it set in 1978, J's can NOT be beat. Name your gin if you don't want a vodka martini, but don't bother with directions like, "and I'd like that stirred..." Just enjoy the era-appropriate everything with your big bowl of booze. J's is a time machine. And big bonus for having a really killer bucket of delicious, local steamers that actually comes IN A BUCKET.

2. For Plotting Against Your Enemies While Enjoying Pretty Decent Drinks in a Dark Library: Shhhh... The Armory.

Okay, please don't tell anyone about this one. I need this joint. You can cozy up to the bar or completely disappear into one of many dark corners, and the entire room is clad in dark wood and bookshelf wallpaper (strangely illustrated spines of books, as if you're in a play set in a library). They tend towards the 90's style martini, complete with a mist of vermouth and shaken to the point of ice shards, but the bartenders are friendly and professional and totally amenable to requests like more vermouth and stirring your drink. They remember your name and often your drink of choice, they have decent beer on tap, they just started stocking Fernet, and they have a free snack plate with that delicious yellow pub cheese that no one will see you wolfing down (because it's so dark). They're busy on Martini Mondays with a lot of industry folks cashing in on drink specials, but they open early every day (11AM) and are often the quietest place in town for an early evening rendezvous or secret retreat.

3. For the Best Sazerac in Town from a Bartender that People Everywhere seem to Know: The Grill Room (and the Original John Myers).

I was in New York a couple of weeks ago, and I found myself chatting with the Tales of the Cocktail American Bartender of the Year 2012. I mentioned Portland, Maine, and he said, "Oh. John Myers!" John Myers (the original) works at The Grill Room Tuesday through Saturday. He hangs with Gary Regan, he shows up in lots of Tales photos, he was once drawn by Dale DeGroff's wife... He seems to be training the other bartenders there well, but if you want a great drink, and if you like your Sazerac twist tossed over the bartender's shoulder, order from the bartender that looks like a magician. (The other John Myers is a swell guy as well, but we'll get to him later).

4. For a Mini-Pitcher of Beer, a Whiskey Back, and a Personal Pizza while Surrounded by Sports and Locals: Pizza Villa.

Ultimate sports dive. Cheap pizza, cheap beer, full bar, cash only, mini-patio, lots of TVs, no attitude, and a low bro-quotient. If you want loads of bros and yards of beers, go to any other sports bar in town. If you want to watch the game with a few friends and walk out with your dignity and some cash left over, go to Pizza Villa.

5. For Good Cocktails and Great Snacks from Friendly Folks with Friends in Tow: Local 188.

Local has been a classic for years and years, but especially since moving to their larger location on Congress Street almost a decade ago. The bar is huge, their wine list is huge, their cocktails are tasty, and they have delicious tapas style eats that are affordable and arrive quick. This is the perfect place to meet for parties of 2 to 12, which will be made pretty obvious by about 7 or so almost any night, when the place starts getting really full. I love ordering a Woodfords Manhattan here. Their sister property, Sonny's, also has great cocktails (try the Wilkinson).

Local 188

Next installment: Newcomers...

AuthorSean Wilkinson