May 2018 | view this story as a .pdf

It’s hard to imagine the Portland we know today, teeming with bars and breweries, as a place where one once had to slink through a backdoor to get a little loose.

By Olivia Gunn

Maine first banned the manufacturing and sale of spirits in 1851, but in Portland, a town built on rum, taverns continued to operate undercover. Rum runners, bootleggers, and the like smuggled in booze, selling it on the sly. Don’t you just wonder what a bar crawl might have been like at the time! If you’re intrigued by shadowy lounges, basement pubs, and raucous dives, come with me. Does anything survive of these early places? Tonight, my wing man is none other than the ghost of Kitty Kentuck, who made a fortune investing in our darker passions.

Catherine Landrigan, a.k.a. Kitty, sailed into the Forest City in 1846. By 1851, she was convicted for selling liquor and sanctimoniously vilified for running brothels. But for all of her court run-ins, Kitty was a woman with reduced options but unquenchable entrepreneurial inspiration. Men envied her business savvy and gift for knowing where and when to earn money, which brought her all sorts of friends in high places. At the height of her financial arc, she purchased property from writer and visionary John Neal, the cousin of Gen. Neal Dow, Portland’s mayor and the Father of Prohibition. To Neal, Kitty was “a poor, but generous, kind-hearted Irish woman.” Poor like a fox! According to Dow, she kept “a notorious groggery” and troubled police, though he did admit (and in his circle this must have prompted gossip) that she was “once very handsome.” But to those visiting Portland in need of a drink and company, Kitty was…Well, perhaps the sailors say it best:

O, I goes down to Kitty Kentuck’s,

I gets my whack three times a day;

Where the ding-bat’s on the table,

Four and six the bummers pay.

Good Time Girl

We start out in the Old Port, where Kitty ran her “boarding house” at 22 Hancock Street, strategically situated to draw clients from the harbor. Searching for a 21st century pairing (even if Stormy Daniels isn’t on CNN on the bar TV as you enter)? Why not try the “cold beer and hot sausage” at Tomaso’s Canteen–a sure fit for a Kentuck kind of night. Tomaso’s sits in a cozy nook off Middle Street. While the spot no longer bears the reputation of its predecessor, Sangillo’s, it’s a refreshing rough-and-tumble alternative to the smooth neighborhood favorites nearby (Eventide, Hugo’s), which Kitty may have considered too tame. Squeezing into the bar at tiny Tomaso’s is a feat in itself during a weekend, let alone grabbing a seat. Luckily, two members of our motley crew have been drinking since early afternoon, and we’re able to saddle up to the bar between them. With “Black Velvet” blaring from the jukebox, we order a round of beers and two tequila shots for Kitty and me. Hang on, it’s time for a “Sweet Caroline” wave.

Downtown & Dirty

Continuing most indiscreetly, there’s no draw in Portland like Rosie’s free popcorn and $1.50 Miller Lite drafts. At this price, someone else is bound to feel charitable and pick up the tab, chest puffed high. I think of the Moon Girl, a fixture on the beer’s logo since 1907, toasting her “champagne,” and imagine she shares the spirit of Ms. Kentuck. Rosie’s pub makes the perfect pit-stop, and, running into more friends, “this round’s on me” rings through the air like a hallelujah. The after-work crowd has started to pack the floor, but we snag one of the dartboards along the back wall and go through the motions of a game. It’s hard to be confident when one friend, Stefan, dares us to call out numbers as he ticks them off one by one. His girlfriend strolls up with, “Call any number. I’ll do it with my eyes closed.” Atta girl!

We can’t possibly continue this crawl without checking into Lincoln’s, the speakeasy below Market Street. Though I’ve been to this bar more than enough times to know where the door is, it gets me every time. Lincoln’s makes for the perfect nightcap joint with its $5 drinks, meaning the bar is usually packed. It’s closing in on 10 p.m., more friends have gathered, and while it’s hard to hear even yourself, the crowd is in a great mood. Groups line the walls, lounging over sofas and corner tables. One posse is nestled in the back of the bar where entertainment typically sets up, its centerpiece a vintage velvet couch–a likely spot for the spirit of Kitty to hold court at the end of a night. As a romantic, I paint a picture of busty corsets, coat tails, and bawdy jokes told through wheezing laughter and sing-alongs.

You can learn more about Catherine Landrigan in Matthew J. Barker’s The Irish of Portland, Maine: A History of Forest City Hibernians. You’ll find she wasn’t handed an easy life. She lost all of the wealth she’d made for herself in the 1866 fire, leaving her destitute in a shanty, where she died at 56. But, as tragic as Kitty’s life ended, she was a self-made woman known to sailors and local politicians alike. I’d have loved just one round with the Queen of the Portland Night.