Well it's certainly not Chicago, but there are some good things happening in downtown Winston-Salem. When I first moved here about 17 years ago, they basically rolled up the sidewalks at 6:00 p.m., and downtown was largely deserted at night. Since then there have been a number of changes and improvements, often baby steps but sometimes larger (like the new downtown ballpark). More and more people are choosing to live downtown, and there are now a number of bars and restaurants that help make downtown an evening destination.
Regarding culture and arts, Winston-Salem is the unofficial "City of the Arts" in NC. The arts are very important, and very visible here. Highlights include the UNC School of the Arts, the 6th St. arts district, SECCA (Southeastern Center for Contemporary Arts), the Reynolda House Museum of American Art, and a number of festivals including the River Run Film Festival, the National Black Theater Festival, the Greek Festival, NC Wine Festival, and others.
Check out Smitty's Notes for current happenings:
Winston Salem, NC Events Guide - Arts, Dining, Entertainment and Community Calendar in Winston Salem, Piedmont Triad, NC