Wicked Wine Run's routes may all wind through lush vineyards, but the races are far from wine snob conventions. In fact, they actively discourage self-seriousness by encouraging wacky race costumes, from a full-body Smurf costume to a vintage suit from a great uncle's closet. After traversing a route cut through rolling hills and leafy trellises, racers return to the winery for a spirited after-party complete with live music and bites from area food trucks.