Winston-Salem is not a college town in the mold of Charlottesville or Ann Arbor, but it is not a cultural wasteland either. Much of life at Wake Forest occurs on campus, but if you want to venture off campus, there are options. Downtown Winston-Salem is consistently getting better and offers some great restaurants and bars. However, there is a geographic disconnect between the city of Winston-Salem and the campus of Wake Forest. Luckily, the new shuttle system alleviates some of this.
If you accept Winston-Salem for what it is—a smaller Southern city—you will not be disappointed. There are great things to do everywhere. Sometimes you just have to look for them. If you cannot find what you are looking for in "the Dash" (as Winston-Salem is affectionately known), the mountains and the beach are only a few hours away by car. Additionally, Wake Forest is within a close drive of Raleigh-Durham, Chapel Hill, and Charlotte, which means you're never too far from North Carolina State, University of North Carolina, and Duke University. Most of your time will be spent on Wake Forest's campus, though, as that is the center of the Wake Forest community.