From North America’s easternmost edge to the city’s iconic promontory, Cape to Cabot is a race of superlatives. It’s 20 grueling kilometers over thigh-burning, knee-jarring hills and inevitably wet asphalt (‘cause let’s face it—it’s October). It bills itself as the “toughest race in eastern North America,” and there’s no question C2C is only for the most stout-hearted runners. 400 racers will compete not just for glory, but for the right to say they completed this insane course without collapsing into a heap in Shea Heights. The race goes October 16. Visit capetocabot.com for race and registration info.