A weekend in Winston-Salem

I know what you're thinking. A weekend in Winston-Salem? What you may not know is that Winston is undergoing a massive transformation. In the past few years, it has grown to be a center for the arts and innovation. I have called Winston-Salem, North Carolina home for the past four years and have enjoyed seeing it blossom.

If you are in need of an affordable weekend getaway, there are so many great restaurants, breweries, wineries and places to stay in "The Dash" as it's referred to by locals. Our baseball team is even named The Winston-Salem Dash. With so many businesses and healthcare opportunities, you may even be coming for an interview or to experience the city. My husband and I have compiled our favorite spots for a weekend in Winston.

Day 1

Early Afternoon

Check into your hotel. If traveling with pets or wanting to stay in a walkable downtown location, we recommend the Kimpton Cardinal Hotel. See a review of our recent stay here. Winston is surprisingly very dog friendly if you want to bring your pup along.

If you'd prefer to stay outside of the downtown area closer to Wake Forest University, we recommend The Graylyn Estate.

Happy Hour

Grab a cocktail at Fair Witness, a funky new downtown bar with a great outdoor space. After sampling a fun cocktail, walk around Bailey Park. There are often events at Bailey Park that are free to the public from movie screenings, to yoga to live bands, so check out their event calendar here.

View of Bailey Park from Fair Witness


There are so many great restaurants in Winston. Some are new to the food scene and others are local staples. For a cozy Southern bistro, we recommend Mozelle's. If going when the evening weather is pleasant, ask for a table outside. They provide blankets if it's a little chilly! If going here, definitely make a reservation in advance. It's a small restaurant, so it's difficult to walk in on the weekends.

Day 2


Wake up and grab a coffee and biscuit from Krankie's. Many don't know you can order from their coffee bar and take it to go. It gets busy on the weekends, so this is a quick alternative to waiting for a table.

A cappuccino and biscuit from Krankie's

With your breakfast in hand, head to Hanging Rock State Park for a hike. It's a 45 minute drive and has several beautiful hikes. The most famous hike is Hanging Rock Trail, but we also love Cook's Wall and there are a couple of waterfalls you can hike to. See more info on the trails here.


Spend the afternoon at wineries or breweries if wine isn't your thing.

After Hanging Rock, consider heading to the Divine Llama Vineyards. This is a well-known vineyard in the area for wine tasting and hanging out with llamas. If llamas aren't your thing, we really like Medaloni Cellars and West Bend. They are really close to each other, so it's very convenient to hop between the two and they are only 15 minutes away from Winston. There are many wineries to choose from in the area. Most have cheese plates and other light snacks to choose from.

The llamas at Divine Llama

Outdoor patio at Medaloni Cellars

If breweries are more your style, we like Wise Man, Fiddlin' Fish and Joymonger's. These usually have food trucks and you can see options on their websites for your dates. There are also some unique shops near Joymonger's full of antiques if that interests you.

Barrels at Joymonger's

Shabbytiques antique store near Joymonger's


Take your pick for dinner! For low-key Mexican, we like The Porch. If the wait is long, we often sit at a small batch, quirky brewery in the same building called Hoots and order takeout. They don't mind you bringing food in. If you don't mind the wait, you can always order a beer or cocktail from Hoots until your table is ready.

If you are celebrating a special occasion, The Katharine is a great choice for ambiance. They have an amazing wine list and I love their French fries. It's located in the Kimpton hotel, so it's convenient if staying there.

After dinner, some of our favorite bars are Vintage Sofa Bar and Bar Pina is the only downtown rooftop bar. It has a fun, tropical theme.

Day 3

Wake up and head to Old Salem for brunch. The Tavern at Old Salem is a local favorite and features traditional Moravian dishes. Old Salem is a historic area of Winston that was originally settled by the Moravians. The area is a living history museum that is a really unique experience. It's located in downtown Winston, so it's also very convenient. They also accept reservations.

Walking in Old Salem

After brunch, consider a tour to learn more. Stop at the Winkler Bakery and buy a Moravian sugar cake to take home.

We hope you enjoy your stay in The Dash.

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© 2019 by Sanara Travels, LLC

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