When I lived there I met most of my friends through a church I attended. It's a very active singles group but yes it is limited. They aren't going to meet you for drinks at a bar although they do go hiking... Overall too conservative for my taste but they were at least a nice group of people.
Calvary Baptist Church
Verge748
First Presbyterian Church, Winston-Salem, NC, Younger Adults
I live in Raleigh now and meetup groups are pretty popular here so maybe check to see if there are any in Winston. If there isn't you could always try starting one, The Dash (
DASH DOWNTOWN! | The DASH ) might even be willing to partner in something like it since it kind of goes along with what they already do.
Reynolda After Hours is another good thing if you like the arts.
Winston Salem Sports & Social Club, Inc. - not sure if this group is still active.