Building a Legacy: A Conversation with Sikes Ragan, the Visionary Behind the Village of Cheshire

What happens when you combine an upbringing on a family tennis camp, architectural studies at Oxford, and a passion for community service? You get The Village of Cheshire—a "new urbanist" community in Black Mountain, North Carolina, that feels less like a standard subdivision and more like a carefully crafted Hallmark movie set.

We recently sat down with Sikes Ragan, the founder and driving force behind Cheshire, to discuss the past, present, and future of this unique "living, breathing" neighborhood.

A Vision Decades in the Making

For Sikes, The Village of Cheshire isn't just a development; it’s a family legacy. The namesake “Cheshire” lovingly memorializes Sikes’ grandmother, a powerful influence in his life. The land itself was home to his father’s tennis camp in the 1970s. While others pressured his father to sell the property, his father held out, believing his son would one day create something special there.

That "something" began to take shape just after graduating from Sewanee- The University of The South; in response to the question of what he wanted to do after college, Sikes crafted a late-night email detailing his vision:

"The Village of Cheshire is a neighborhood where you have the freedom to work and play within a five minute stroll. You may live in a residential home, a town home, or a studio apartment meshed into the neighborhood market place. Tennis and swimming along with scenic hikes in the Blue Ridge Mountains brings you to a self-realization of your potential strength as a human being. Education is a part of any great experience; you will find many opportunities for enrichment here at The Village of Cheshire. Health is the topic and food and exercise are the chapters. From dicing locally grown fresh vegetables with a master culinary chef to sharing nutritional puzzles, you will find laughter to be that genie you always wished you had. Taking an active role in seminars, exercise classes, or time to yourself is the key to taking advantage of your stay at The Village of Cheshire.  Your stay may be for a lifetime, a weekend or even an early morning water aerobic class. It is important that you feel at home. This special place is a home for many people as they walk to work with a child in one hand and a newspaper in the other. The local restaurant gives a place to grab a quick bite for lunch and a leisurely dinner with friends in the evening. If you don't return for the food, you will certainly return for the atmosphere. Whether it is a special time of year, a needed vacation or a place you call home, it is The Village of Cheshire that gives you a new sense of place. I invite you to come and stay awhile.”

This wasn’t just an idea- it was a prognostication. 

After graduating, Sikes studied architecture and urban planning at St. John’s College in Oxford. Inspired by the simple beauty of English Tudor style and by the Arts and Crafts movement, he returned with an even clearer mission.

This unwavering dedication to his original vision has become the driving force that shapes The Village of Cheshire today.

The "Sikes Process": Architecture and Artistry

Building a community that blends into the local North Carolina vernacular- rather than looking like "a landing from Mars"- requires an immense amount of coordination. Sikes emphasizes the importance of a strong team to manage the "squeaky wheel" of development.

• Master Planning: The village was laid out using a "Charrette process" in 1998 by the world-renowned firm Andres Duany, Elizabeth Plater-Zyberk & Company (notably known for their work planning the town of Seaside, Florida). The firm developed architectural design standards for The Village of Cheshire that derive from local vernacular, blending materials, roof pitches, and front porches from Montreat, North Asheville, Chimney Rock, etc.

• Architectural Design: Currently, Sikes works closely with Bill Harris of Allison Ramsey Architects, a firm that specializes in this New Urbanist neighborhood design. Because of this refined skill in New Urbanism, they are able to pull from other projects and work with momentum.

• Strategic Partnerships: An essential portion of Sikes’ process includes having a good design build contractor and team for the inevitable obstacles that arise in construction. 

“It takes so long to go from an architect to an engineer, back to an architect, to the planning department, back to permitting, then back to the architect to tweak any concerns that the builder inspector might have questions about. Matt Keene with Buchanan Construction has been instrumental in connecting the dots, crossing the T’s, and dotting the I’s to help facilitate and pull it all together on the commercial side and the residential side.”

What’s Next for The Village of Cheshire?

While the Jacobs Cottages- named after the legendary urbanist Jane Jacobs- are nearing completion, the most ambitious phase is still ahead. The focus has now shifted to the Town Center, which will feature:

• An authentic Main Street with ground-floor retail and loft living above.

• A boutique hotel featuring a beautiful event center for weddings and banquets, and a family-style "supper event area" for locals and visitors alike.

Beyond the physical buildings, the Cheshire Foundation (a 501(c)(3) non-profit) is growing. The foundation focuses on enriching lives through "placemaking" education, community concerts and events, public art, and maintaining walking trails and parks for the entire community at large to enjoy.

A Lasting Precedence

When Sikes started this journey, local newspapers called him the "25-year-old developer". Decades later, his motivation remains the same: setting a precedent for high-quality, thoughtful growth. It’s about “how we grow, where we grow, and why we grow," Sikes explains. 

By naming every street after literary figures- like Dunn, Longfellow, or Fay Jones Lane- he has ensured that every corner of the village tells a story.

The Village of Cheshire is projected to reach complete build-out in the next five to seven years, fulfilling a vision that began with a family legacy- and a single email sent at 1:00 AM in college creating a new sense of place.