Twin Oaks Tavern Winery - An Inspiring Woman Owner Story

Yubo Zhang
Nov 16
3 min read

Updated: Nov 16

This weekend, Mrs. Qin Chen and I had an absolutely amazing conversation with the owner of Twin Oaks Tavern Winery, Michelle Spear. Nestled in the breathtaking Blue Ridge Mountains, this winery is truly a hidden gem! Michelle shared that, amidst all the craziness happening in our country, especially being so close to Washington DC, the winery offers a warm and inviting home-like atmosphere that lets visitors escape the chaos and rediscover the tranquility and beauty of nature. This reminded me of stories I heard when I visited Big Sur in California and museums in Colorado, about how arts and literature thrived during times of big recession or extreme political polarization. Mrs. Spear has adorned the walls with paintings by local artists as a way to support struggling artists. There will also be live music open mic after January 2026. In my view, twin oaks tavern is beyond just a winery but a hub for reconnection. Reconnections among general people over relaxing conversations, reconnection with our soul through arts and music, and reconnection with our mother nature. Mrs. Qin Chen beautifully captured the essence of the winery in a portrait that perfectly aligns with and resonates with HowSheLeads' mission and vision.

"Life beats down and crushes the soul and art reminds you that you have one." - Stella Adler

1. A Story of Female Legacy: Passing the Torch from Donna Evers to Michelle Spear

Twin Oaks Tavern Winery sits along the Blue Ridge Mountains in Virginia. Originally built in 1904 as a mountain inn, it was later transformed into a winery and operated for 26 years by its previous female owner, Donna Evers. In 2025, this legacy was passed to another woman—Michelle Spear. In industries traditionally dominated by men—agriculture, winemaking, land stewardship—this ‘woman-to-woman’ transition is rare and powerful. What Michelle inherited was not merely a business, but a lineage of trust, craftsmanship, and a gentle responsibility toward the land.

2. Sustainability and Land Philosophy: Protecting the Terroir Through Ecological Stewardship

One of Twin Oaks’ defining characteristics is its commitment to sustainability—rain-fed vines, bee partnerships, and biodiversity preservation. For Michelle, the land is not a resource but a living organism; running the winery is not extraction but stewardship.

3. Design & Atmosphere: Turning the Winery into an ‘Emotional Home’

With a background in design, Michelle personally redesigned and refreshed the winery after taking ownership. The space reflects her own qualities—quiet, warm, textured, and deeply comforting. This is her distinctive form of leadership: leading through space and atmosphere rather than authority.

4. A Women-Centered, Family-Driven Team Culture

Michelle’s winery does not operate under a corporate structure. Instead, she has built a multi-generational, women-centered team: her daughter co-runs the winery, her daughter’s female friends work there, and her husband supports during busy weekends. This structure is warm, organic, and deeply aligned with values of women’s leadership.

5. Leadership Through Genuine Care: Service as Connection, Not Transaction

You observed a powerful moment of leadership: even though you ordered only an inexpensive cup of coffee, Michelle and her daughter offered warm, thoughtful service. She treats every visitor with equal sincerity. When she saw a group of older friends enjoying their afternoon, she expressed genuine pride and joy. This is a form of women’s leadership rooted in care, not transaction.

6. Empowering the Next Generation: Creating Platforms for Young Girls

Unlike most wineries, Twin Oaks’ live music features young girls—ages 11 to 14—performing piano, guitar, and vocals. Guests love it, and these young performers build confidence through the experience. This is one of the purest expressions of women’s leadership: creating opportunities for the next generation to be seen and heard.

7. The Winery as an Emotional Community Rather Than a Business

The interactions happening in the winery—retired friends gathering, the family working together, young girls performing, visitors relaxing—create a space filled with emotional warmth. Michelle isn’t running a winery; she is cultivating a place people want to return to. This is women’s leadership at its deepest level: leading through relationships, not hierarchy.