40 p o r t l a n d monthly magazine Portland after dark 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 cen- tury 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 Ken- tuck kind of night. Tomaso’s sits in a cozy nook off Middle Street. While the spot no longer bears the reputation of its predeces- sor, Sangillo’s, it’s a refreshing rough-and- tumble alternative to the smooth neighbor- hood 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 or- der 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 Bramhall sits just steps from the home of the Father of Prohibition himself and Kitty frenemy Neal Dow.Just before you reach Dow’s former residence,you’ll pass the location (the balcony,where employees could wave to passersby,is a tell) of the once- infamous Parisienne Sauna,a salacious “massage parlor” up until the 1980s.Whiskey to the left of him,sex to the right “At Lincoln’s,I paint a picture of busty corsets, coat tails,and bawdy jokes told through wheezing laughter and sing-alongs.” The Dance Hall Augustus King once ran a dance hall and brothel on Munjoy Hill, the location of the crudely named “Whorehouse Riot of 1849” that left several wounded and one man dead. According to Trudy Irene Scee’s Dancing in Paradise, Burning in Hell: Women in Maine’s Historical Working Class Dance In- dustry, the riot started after a July 4th argument between King and a group of sailors. Following several brouhahas that summer, including one imbroglio involving a cannon fired into King’s home, an angry mob gathered on King’s property and set fire to his dance hall.