So, I found myself with a bit of free time and Winston-Salem popped into my head. Heard a few folks mention it, you know, as a place with some charm, so I figured, why not? Didn’t do a whole lot of planning, to be honest. Sometimes I think over-planning just ruins the surprise. Just packed a small bag and off I went.

First Impressions and Old Salem
Alright, landed in Winston-Salem, and the first big thing on my mental checklist, and pretty much everyone else’s it seems, was Old Salem. So, I headed over there. Walking around Old Salem was like stepping back in time, for real. The old buildings, the folks in period costumes, it’s all very immersive. I spent a good few hours just wandering the streets, popping into the little shops and houses they have open. Some of the craft demonstrations were pretty neat to watch.
My main takeaway from Old Salem? It’s definitely something to see, especially if you’re into history. It felt pretty authentic. I bought some of their ginger cookies, of course. You kind of have to.
- Spent a lot of time just soaking in the atmosphere.
- The bakery was a highlight, naturally.
- Chatted with a few of the interpreters, they really know their stuff.
Next Up: Reynolda
After Old Salem, I thought I’d check out Reynolda. Heard about the Reynolda House and the gardens. Started with the gardens. Man, those gardens are something else. So peaceful. I just strolled around, found a bench, and chilled for a bit. It was a nice change of pace after the historical hustle of Old Salem.
Then I went into the Reynolda House Museum of American Art. Now, I’m not a huge art connoisseur, but I can appreciate nice things. The house itself is impressive, grand, you know? And the art was interesting. It’s a different vibe from Old Salem, more about that early 20th-century wealth and culture. Liked seeing the original furnishings and all that. They even had a bowling alley in the basement, which was a bit of a surprise.
Downtown and the Arts District Vibe
Later on, I made my way to the downtown area, specifically the Arts District. Heard it was a cool spot. And yeah, it had a good feel to it. Lots of galleries, little unique shops. I wasn’t really in the market to buy art, but it was fun to look around. Walked past a bunch of murals, which always brightens up a city space, I think.

Found a little spot for dinner, one of those local places, not a chain. The food was decent, and the atmosphere was pretty laid back. Seemed like a lot of locals were out and about, which is always a good sign. I think I grabbed a beer at a local brewery too. They seem to have a few of those popping up everywhere these days, and Winston-Salem is no exception.
So, Was It Fun?
Yeah, I’d say Winston-Salem was a good trip. “Fun” is a subjective word, right? For me, it was a good mix. Old Salem was interesting, Reynolda was beautiful, and the downtown area had a nice, creative energy. It’s not a massive, overwhelming city, which I appreciated. You can actually walk around and see things without feeling rushed off your feet.
I didn’t hit every single attraction, I never do. I like to leave some things for a “maybe next time.” But what I did see, I enjoyed. It’s one of those places that has its own distinct character, and I’m glad I took the time to go check it out. If you’re looking for a place with a bit of history, some nice scenery, and a relaxed artsy vibe, then yeah, you’ll probably find some fun things to do in Winston-Salem. I sure did, just by wandering around and seeing where the day took me.