Portland after dark M AY 2 0 1 8 3 9 meaghan maurice Naughty Portland 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 Kostishevskaya Maine first banned the manufactur- ing 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 con- victed for selling liquor and sanctimo- niously vilified for running brothels. But for all of her court run-ins, Kitty was a woman with re- duced options but unquenchable entrepreneurial inspiration. Men envied her business savvy and gift for knowing where and when to earn mon- ey, which brought her all sorts of friends in high places. At the height of her financial arc, she pur- chased property from writer and visionary John Neal, the cousin of Gen. Neal Dow, Portland’s mayor and the Father of Prohibition. To Neal, Kit- ty 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