I thought James Taylor was from Chapel Hill. They even have a bridge named after him in CH.
But back on topic ... yes, if you can find a house near the historic part of Hillsborough, you could easily walk to the handful of restaurants on Churton Street. They even have a blues club if you're into that sort of thing. Weaver Street Market is opening a location there, so a grocery store will soon be in walking distance for people living in that area, too.