In 1929, Chicago saw Valentine’s Day turn bloody as Al Capone and thugs gunned down seven mob rivals. That event is the gruesome inspiration behind the St. Valentine’s Day Massacre Cruiser Ride, devised by TT Roadhouse owner Rick Skoog and Ska Brewing. “We decided to do a Valentine’s Day Massacre ride and get people to dress up like massacre victims,” he says. “That didn’t so much work, but the ride stuck.” Last year, a handful of riders -- out of 110 total -- got into costume. But Skoog says they're not really pushing the dress-up thing.
The free ride begins at TT, meanders to Papago Brewing, Rogue Bar, Well Bar, and then back to TT. Basically a “booze cruise,” the longest pedaling stretch is 1.2 miles—just far enough to biff it and embrace the theme.