Free outdoor concerts take place every Thursday, Friday, and Saturday night from May through September. Movies from the North Carolina School of the Arts (NCSA) School of Filmmaking are shown in the 1,300-seat Stevens Center to some of the largest audiences of any independent film theater in the country. Rock the Block, a street festival initially created to celebrate the "new" Fourth Street, has now become an annual event attracting tens-of-thousands. Other popular people-magnets include the Fiesta Hispanic Festival, the RiverRun International Film Festival, and the internationally acclaimed National Black Theatre Festival. Adding to this prime time menu of entertainment will be the region's first downtown multiplex cinema and IMAX Theater.

In addition to being an entertainment hub, downtown Winston-Salem is the urban dining destination of the Triad. The Restaurant Row program is attracting diners throughout the region. With funding from HUD, the city has been providing direct loans for new downtown dinner restaurants. The allure of the dining destination reflects the fact that there are no national franchises present. What is here is strictly local and largely unique to Winston-Salem and the region.