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Apologies to Hunter S. Thompson, but there's nothing decadent about horse racing in 2013. Now that the sport of kings has been lowered to plebeian level, though, a day at the races holds a certain retro-patriotic charm if you can avoid asking yourself, "Do these magnificent creatures actually enjoy running in circles with human-shaped backpacks strapped to them?" An afternoon at Portland Meadows (1001 N Schmeer Road, 285-9144, portlandmeadows.com) is, simply put, one of the best day-drinking experiences in town. A rebranding campaign playing up the track's 67-year history with nostalgic, Rockwell-style artwork has effectively turned the Meadows into the biggest hipster-gentrified dive bar in town. On opening day, a horde of 20-somethings dressed for a Mad Men theme party gathered at an outdoor tent for a "craft beer festival," while inside the track, real-life Freddy Rumsens sat rumpled beneath the two-dozen television screens hanging above the bar, no doubt perturbed that it was suddenly taking the overwhelmed staff 20 minutes to crack open their Bud Lights. The old-fashioneds and mint juleps ($6 each) are sweetened beyond recognition, and the best you—as in, the novice who places bets purely based on the horse's name—can ever hope to do after five hours is break even. But there's an undeniable, near-primal thrill to standing on a bench, winning ticket in hand, and screaming, "Picture Me Rollin'!" That's the name of the horse, you see.
WWeek 2015