I live in High Point but was born and raised in Winston-Salem. I can give you some info based on my experience living there. I find myself in Winston two or three times a week, so I'm still somewhat in the loop, although not nearly as much as when I lived, worked and played there. (FWIW, I have a personal policy against even driving through Charlotte, much less going anywhere in or near the city. The traffic is maddening.)
Advantages of living in Winston include relatively light traffic for a fairly big city (Hanes Mall Blvd and Stratford road excluded) and its fairly close proximity to surrounding areas you may want to visit for shopping, entertainment, etc. Get on I40, which runs right through Winston, and it's a straight shot to Greensboro and only a 30-45 minute drive depending on where in Greensboro you're going. If you live in Winston, you may find that you drive to Greensboro fairly regularly. Besides the GSO airport, which most of us fly out of when we travel, there's decent shopping in Greensboro not to mention shows/concerts at the Greensboro coliseum. Also, lots of folks in Winston work in Greensboro. I did for years and didn't mind the commute at all. There are clubs and bars in Greensboro, but we had enough in Winston back then that there wasn't any point in making the drive. (With I40 and US52 both running through Winston, Greensboro isn't the only city that's just a few minutes down the road. It's situated perfectly for traveling around the state and back fairly easily.)
Speaking of clubs/bars, the Burke Street bars are a fun place to hang out on the weekends with friends. On Burke St near downtown Winston are several bar/clubs right in a row and if you didn't live in Winston you might not know about them. Nice mix of people but not packed full or blaring obnoxiously loud music. Young professionals, folks from the downtown hipster music crowd and college students all enjoyed that scene and there was never any trouble or drama that I recall. (Keep in mind, my memories are from years ago, but I'd be surprised if much has changed.)
We also got into going to baseball games to watch the Warthogs play (Winston's Triple-A team at the time). We'd go to night games, then head down the street to one of several sports bars where the teams would also gather. We got to know a lot of them and they were fun to party with. Watching baseball wasn't something I ever thought I'd get into, but a couple of girlfriends and I really came to enjoy the games during summertime and became fans of the team.
Unless things have changed in the past few years, Winston went through a major downtown revitalization project a while back. At the time, the mayor was trying to get everyone to start calling it "uptown" but that never caught on. But events were held on Thursday nights on sometimes on the weekends featuring jazz music or something like that. They were free to attend and were geared toward families but it was still cool to go hang out every once in a while.
Other events/places you might be interested in are:
The NC Wine Festival is held every year at Tanglewood Park in Clemmons, NC, just west of Winston but still in Forsyth County. If a wine festival doesn't sound like your thing, I'm with you. However the one at Tanglewood every year includes live entertainment, merchant exhibits from all over NC displaying everything from tie-dye shirts to perfume to jewelry, lots of food and of course, wineries from all over the state serving and selling their products. If this is your kind of thing, pay extra for VIP tickets. Otherwise, prepare for a parking nightmare, bring camping chairs, and dress for a hot day. Depending on where you sit, there may be annoying loud music that makes light conversation difficult. My dad and brothers went last year and it got a little rowdy for a wine festival. I don't plan to go any time soon, but they enjoyed it.
For outdoor activities, you could head north on 52 to
Pilot Mountain State Park. Pilot Mountain's not exactly a tourist attraction but that makes it even nicer to visit. It's beautiful and well-maintained and is a great place for hiking, fishing, biking and camping. Here's a link if you're interested.
http://www.ncparks.gov/Visit/parks/pimo/main.php
Most people visit
Biltmore Estate in Ashville, NC at least once. Some visit just about every year, usually around Christmas. It was nice but I didn't care to make it a regular thing. But if you live in NC, it's worth at least the one trip.
For vacations within driving distance, you could go to a NC beach. But my advice is to drive the extra hour to Myrtle Beach or North Myrtle Beach in South Carolina.
Hope this helps! And if not, I had fun writing it and looking back on memories of good times when I lived there. I'll be happy to answer any questions you may have about specific areas, schools or neighborhoods.
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