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7 Wonderful Women-Owned Businesses in Winston-Salem that are Killing It!

Published by Christina Riley. Last Updated on March 9, 2024.

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There was once a time when women-owned businesses in Winston-Salem were overshadowed by the smoke-filled (and men-dominated) boardrooms of the city’s tobacco giants. Or so it would seem.

Because for many of Winston-Salem‘s years of existence, there have been plenty of women making changes in the community, whether in business or education. Today, we recognize them as the “Winston Waymakers,” from the Moravians to today.

These women are still changing the city and moving it through to a future so that women-owned businesses in Winston-Salem will have an equal place at the table. Here are a few stories of current and previous waymakers, starting at a time when Winston and Salem were two separate places.

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Women-Owned Businesses in Winston-Salem NC and Their Backstories

Note: We know that there are many Winston-Salem women-owned businesses that are killing it. We did not intentionally leave anyone out, but found these women’s stories interesting and compelling to share! If you would like to nominate a business to be featured for an interview, please email us.

Single Sisters of Salem

Old Salem NC Image

Did you know that the oldest educational institution for girls and women in the United States is in Winston-Salem? The Single Sisters House of Salem College was built in 1785 and served as a school for the women who settled Salem after making the 500-mile trek from Bethlehem, Pennsylvania.

In the center of Old Salem, unmarried Moravian women taught each other. This progressive educational allowance is noted as one of the reasons Moravians were such successful entrepreneurs.

Because this was the first institution to value equal opportunity and female education, it inspired many generations of Winston-Salem women.

Reynolda House

Female Owned Businesses in Winston Salem NC Reynolda Image

While RJ Reynolds was the face of tobacco in Winston-Salem, the Mount Airy-born Katharine Smith Reynolds was more than just the lady by his side. RJ and Katharine’s marriage was a very progressive one.

That’s because Katharine had more power and decision-making abilities than any typical woman during the early 1900s.

Today, you can learn about Katharine by touring the Reynolda House Museum of American Art, one of the most popular things to do in Winston-Salem. While today’s museum may be affiliated with Wake Forest University, the building and decor were completely designed by Katharine.

She worked with landscape designers and architects to make it technologically advanced for the time.

However, Katharine’s biggest legacy goes well beyond this historic home. Katharine saw improvements that needed to be made in her husband’s factories and became a champion for women’s suffrage and better work environments.

She fought for hot lunches and water fountains as well as providing a nursery for mothers working in the factory.

Read More: The Katharine Brasserie and Bar in Downtown Winston-Salem (One of the City’s Best Eateries!)

Mary’s Gourmet Diner

In 2020, Mary’s Gourmet Diner closed its doors. And while we would usually edit our article to reflect that, we think that Mary’s had such a profound impact on women-owned businesses in Winston-Salem that we decided to keep it on this list.

When she first opened the diner that bears her name, Mary’s was one of the first Winston-Salem restaurants to source locally. Today, her legacy goes far beyond fresh sustainable meals.

Mary’s story of loss, finding herself through sobriety, and success is one that is both heart-wrenching and inspiring. Beyond her business, she believes that sharing her story of failures, lessons, and successes is important for everyone to learn from.

In 2016, she created a free support group for local female entrepreneurs called Mary’s Mavens. And within a couple of months, more than 500 women were showing up to empower each other.

Note: Many of the other female business owners in this article mention Mary and this group as the cornerstone of their success.

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Humble Bee Shoppe

Brittany McGee Humble Bee Winston-Salem NC Photo Credit Kristin Welch of The House of Ivy
Photo credit to Kristin Welch / The House of Ivy.

Brittany McGee of Humble Bee Shoppe is among the many who are grateful to Mary’s Maven creating a space for women to build each other up. As a UNC Greensboro student, Brittany used baking as a way to relieve her stress but didn’t see herself becoming a bakery owner anytime soon.

In 2016, Brittany gained courage after listening to Lawren of a/perture (see below) speak at a meeting. Afterward, McGee decided to overcome her fears and create her own destiny.

Brittany says she’s proud to be a woman business owner and Waymaker because, as she puts it, “I am living out a dream, working hard every day, and proving to myself that I can do the things I set out to achieve.”

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Elasya B’s Candy Tree

Women Owned Businesses in Winston Salem NC Elasya Bs Candy Tree Image

Meet one of our youngest Waymakers, Elasya B. After you read more about her, you’ll likely assume her journey is an example to be followed by women of all ages.

This business owner sold her first homemade candy apple when she was nine years old. Requests for more kept coming in. And that’s when her parents asked Elasya what she wanted to do with all the money that she was earning.

Unlike most kids her age, Elasya wanted to keep investing back into the business. So in 2012, without a business loan, she and her family opened Elasya B’s Candy Tree.

Her downtown store is filled with homemade cupcakes, cotton candy, and incredibly decadent dipped pretzels. In talking with her father at the store, it is clear that supporting her dreams helped Elasya become an entrepreneur.

Personally, my biggest takeaway from one of the youngest women-owned businesses in Winston-Salem is to keep investing in yourself and your dreams. Why? Because your passion can and will change our world.

Sweet Potatoes Restaurant

Women Owned Businesses in Winston Salem NC Sweet Potatoes Restaurant Image

Stephanie Tyson and Vivián Joiner opened their iconic Sweet Potatoes restaurant nearly 20 years ago. And after eating there, I learned that the incredible food isn’t the only thing that makes this restaurant an institution.

From the moment you walk into Sweet Potatoes in downtown Winston-Salem, you feel the warmth that only a woman-owned business can provide. Even though they’ve overcome quite a few obstacles and challenges, these women don’t believe that they are trailblazers.

Instead, they are doing what they believe women are destined to do. Vivián says the future for female ownership is bright.

“The only limits are the ones we allow to be placed in our path.”

She also shared the belief that women are destined to achieve. The strength that women bring to the table is that, as she explained, “women see what should be done and find a way to do it.”


Lawre Desai Winston Salem
Photo Credit: Alyson Rorem, Jasper & Fern.

The woman-owned theatre a/perture is more than just a place with great flicks. By utilizing one of the most accessible art forms—film—this spot on Fourth Street is bringing the community together to see films that likely aren’t found anywhere else in the area.

That was a major goal of Winston-Salem born Lawren Desai’s when she opened a/perture. She wanted to share independent films as a unique collaboration between artists and the community.

Lawren is deeply ingrained in the community, as she serves on the Arts Council board, the Arts-in-Education grant panel, and as an advocate for childhood literacy.

When I talked with her, Lawren noted that women are more aware and can call others out or ask questions if they feel like they are being stymied by their gender. She also offers advice to other women daring to open their own businesses:

“If you don’t 100 percent believe in what you are doing, no one else will. Be willing to take risks and change directions, because nothing is ever guaranteed and you have to remain flexible.”

Final Thoughts

Something struck me while chatting with these women- the idea of shifting the definition of women and their roles. When you think back a generation or two, society had long presented women as demure, subservient, and best kept in the background.

But today, women like these strong and empowering Waymakers are redefining roles. Honestly, I don’t think women are changing, because we’ve always been strong.

It’s that society is finally figuring it out. As a result of more women owning their own businesses and kicking ass, there’s room for more balance.

To close things out, I wanted to share some advice Humble Bee Shoppe Owner Brittany McGee offered for all women out there who are scared to even try before starting:

  • Please be kind and softer to yourself. 
  • Please show yourself the love you so desperately wish you could give someone else. 
  • And finally, please believe that you are actually capable of great things. Also, you can indeed execute them if you do the work you were meant to do.

Thank you so much to the women both in this article and beyond who are creating spaces to empower and uplift each other.

There are so many women-owned businesses in Winston-Salem and these are just a few of the incredible stories. To find more women-owned businesses in Winston-Salem, check out this directory from Fearless Winston Salem.

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