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While you may spend all day long out at the countless distilleries around the heart of the city, you may spend all night getting your Urban Bourbon Trail passport stamped at various locations around the city. The Urban Bourbon Trail consists of historic hotel properties that once served Kentucky whiskey to the likes of Al Capone and F. Scott Fitzgerald and cosmopolitan "scenes" where urban trendsetters are making retro drinks, such as the old fashioned and Manhattan, according to the attraction's website. Visitors can pick up their passports from any of the participating stops along the way or at the visitors' center. Get six stamps and there is a prize waiting for you!