Many of the people I know seem to think there isn’t a whole lot to do in Winston Salem. But every time I’ve been, usually for a short weekend trip, I feel like I don’t have enough time. Something about this adorable artsy town reminds me so much of my hometown that I always leave wishing I had stayed longer. If you happen to be passing through and only have 24 hours in town, here is one of my favorite ways to spend an art-filled day in Winston-Salem!
A day in Winston-Salem
If you let it, I think Winston Salem can surprise you. As a city, it is full of history and it embraces the arts, much like my hometown of Sarasota, Florida. With a reputation for innovation, the city really has found a way to be an artsy destination filled with a rich history and a culture all its own. With its proximity to North Carolina’s wine region, Yadkin Valley, if you find yourself in town for a day, here is how I recommend you spend it.

Morning
Start your day with breakfast at Mary’s Gourmet Diner. You’ll get a great introduction to the Winston Salem arts vibes too since it is decorated with local artists’ work and a hang out for those in the scene. They have an ever-changing specials menu that ranges from Unicorn French Toast to Texas Pete benedicts you can try but the breakfast nachos are where it is at.
Mary’s will also give you a taste for local with many of their ingredients being as farm to table as you can get. They really pride themselves on serving up dishes that embrace their sustainability practices and benefit the community.
After you’ve filled up at Mary’s Gourmet Diner., head to the downtown art district by taking a left out of Mary’s to stroll Trade Street. Along the streets that make up Winston Salmen’s arts district, you’ll find galleries, shops, and murals. In the avant garde art galleries and eclectic shops, you’ll find some unique pieces that make great souvenirs or gifts.
Afternoon
When you’re ready for lunch, head to Reynolda Village. The Reynolda Historic District was once part of the country estate developed by Richard Joshua Reynolds and his wife, Katharine Smith Reynolds. Reynold’s made his money in the tobacco industry. The estate was modeled after traditional English villages and included dairy barns, a cattle shed, school, post office, smokehouse, blacksmith shop, carriage house, as well as cottages to house the family’s chauffeur and other estate employees.
Today, the Reynolda district serves as an educational, cultural, and community complex for the local community, keeping with the Reynolds’ original mission and plan. Buildings that once served as dairy barns, cattle sheds or blacksmith shops now house shops and restaurants.
Grab a burger at Village Tavern one of the most popular restaurants in the city that is located in the original dairyman’s cottage. After lunch, you can head over to the Reynolda House Museum of American Art and enjoy the estate’s gardens.

The Reynolda House Museum of American Art is the 1917 home the Reynolds live in and houses a very large collection of American Art. The collection includes pieces by Georgia O’Keefe among other famous artists. And at 2:45 pm you’ll want to be in the Reception Hall to hear the home’s original Aeolian organ fill the halls with music.

After spending some time at Reynolda, you can head over to Old Salem and spend some time at the Old Salem Museums and Gardens. This historic district is a living museum with cobblestone streets and potters workshops showcasing the beautiful pottery the area is known for. If you have time, or just need a snack to hold you off until dinner, try the fresh bread at Winkler Bakery. I am a big fan of their sugar cake!

Evening
For dinner, I recommend going to The Katharine Brasserie for a glass of wine or cocktail and fresh seafood. Named after R.J. Reynold’s wife, the restaurant is situated in the former Tabacco Company headquarters which brings your day in Winston Salem full circle.

There is so much more to see in Winston Salem and if you want to do a longer stay, I recommend at least 3 days to really experience the city to the fullest. But, I get it. Life happens and sometimes you only have time for a quick 24 hours visit so I hope this helps you fall in love with one of my favorite North Carolina areas.