By Gene Galin
Pittsboro, NC – What began as an informal lunchtime conversation about restaurants, local personalities and old business deals quickly widened into a debate over Pittsboro’s future: whether our rapidly growing town can develop a distinctive identity built around public art, locally owned businesses, connected greenways and memorable public spaces — without allowing fragmented planning or generic development to define it instead.
Our July 12 installment of “3 Guys from Pittsboro Having Lunch,” at Doherty’s Irish Pub & Restaurant with Lyle Estill, was somewhat loose, humorous and sometimes sharply argumentative. Yet beneath this banter was a serious question facing Pittsboro as Chatham Park, new residential projects and the planned relocation of county offices transform the physical and economic landscape surrounding the historic courthouse.
“What is our strength as a town?” Estill asked during the conversation. “You’ve got to find the niche that you can inhabit, and then you have to exploit that niche.”
His answer was direct: Pittsboro should become known for art, food, entertainment, entrepreneurial experimentation and pedestrian connections — attractions powerful enough to persuade residents of Chapel Hill, Raleigh and communities east of Jordan Lake to make the trip.
That argument closely parallels language already appearing in Pittsboro’s official planning documents, which describe downtown as an aspiring “vibrant arts and cultural destination.” But Estill’s proposed scale, urgency and unconventional tactics illustrate the distance between endorsing a vision and implementing it.
Our conversation also exposed unresolved tensions: private property rights versus the town’s public image, downtown preservation versus housing and office development, public investment versus private entrepreneurship, and the role of advisory boards in decisions involving publicly owned land.
The result was not a polished development proposal. It was something more characteristic of Pittsboro — an unruly civic brainstorming session conducted over lunch.
A Lunchtime Conversation Becomes a Discussion About Identity
The discussion opened with the fate of local restaurants, including the former Postal Fish Company, which we remembered as a favorite destination for higher-end dining.
Lyle Estill wondered whether the arrival of Doherty’s had contributed to Postal Fish’s departure, although Greg Stafford rejected a simple cause-and-effect explanation and said the restaurant’s owner had become tired of operating it. The exchange soon expanded into a broader concern: whether Pittsboro currently offers enough distinctive dining experiences to attract people from outside the immediate community.
Estill recalled the Hilltop restaurant, once located at what is now Davenport’s Café Diem, as an establishment that drew customers from Chapel Hill and Raleigh. He described an earlier period when customers dressed for dinner and were served by formally attired waiters. In his view, Pittsboro once had restaurants that were destinations in themselves, rather than convenient places serving primarily local customers.
That distinction matters to downtown economic development. A restaurant serving people who already live or work nearby circulates money within the community. A restaurant that brings diners from outside Chatham County introduces additional spending that may spill into shops, galleries, entertainment venues and other businesses.
Pittsboro is already marketed as a day-trip destination with independent shops, bakeries, breweries and restaurants surrounding its historic core. Regional travel coverage has described downtown as a growing small-business district within easy driving distance of Chapel Hill, while the county’s tourism agency promotes Pittsboro and Siler City as destinations for food, art, recreation and special events.
Still, Estill argued that Pittsboro needs more than a collection of pleasant businesses. It needs attractions powerful enough to overcome the psychological and geographic barrier of Jordan Lake.
“What I’m trying to do is get customers and get reasons to come across the lake,” he said.
Estill’s Model: An Industrial Site Turned Community Destination
Estill’s perspective is shaped by The Plant, the former industrial property on Lorax Lane that he and his partners helped convert into an unconventional collection of food-and-beverage businesses, retail operations, event spaces, art installations, gardens and outdoor gathering areas.
The property was once associated with a flower-growing operation and later housed an aluminum manufacturing facility. It was acquired in 2005 by a group initially interested in biodiesel production. Over time, it evolved into a business campus featuring food, drinks, music, art, markets and recreational activities.
Estill is described by The Plant as a former technology entrepreneur, studio artist and author who now helps operate The Plant and Fair Game Beverage Company. His published work has frequently focused on biodiesel, sustainability, local economies and community-scale enterprise.
The Plant’s development was incremental rather than the product of a conventional master plan. Businesses, artwork, events and landscape features accumulated over time. That experience informs Estill’s insistence that memorable places are created by repeated additions rather than a single construction project.
“What I’m doing down at The Plant is no different from what everybody is doing everywhere,” he said, noting the popularity of outdoor food-and-beverage campuses, breweries and mixed entertainment venues. “What’s the difference between mine and the other five million of them? … The answer is art.”
The Plant now describes itself as a food-and-beverage campus centered on local business, events, art and music. Its grounds include an art walk, outdoor installations, performance areas and a sculpture celebration intended to encourage businesses to purchase pieces for a potential art corridor along U.S. 64.
The model offers one possible answer to a question confronting many small towns: How can a community create a recognizable destination without imitating a shopping center, entertainment district or master-planned development found elsewhere?
For Estill, the answer is not merely to build restaurants or install landscaping. It is to create an environment that visitors photograph, discuss and remember.
“Artify” Pittsboro
Estill’s proposal is what he called “Artify” — a coordinated public and private investment campaign that would place substantial, highly visible artworks throughout Pittsboro.
He proposed that several participants — potentially The Plant, Mosaic at Chatham Park, the town, Chatham County and private businesses — each contribute roughly $10,000 annually. Sustained over four years, he argued, the combined investment could create a critical mass of sculptures and installations that would turn Pittsboro into a regional arts destination.
“At the end of four years, this town would be a destination that people would be coming to see,” Estill said.
He contrasted major installations with smaller purchases such as decorative bike racks or benches. His argument was not that functional art lacks value, but that minor additions alone are unlikely to generate regional attention.
“You want to move the needle around here?” he asked. “It’s not going to be with a butterfly bike rack.”
Eric Andrews pushed back, noting that the town is already purchasing and installing art. The conversation referenced benches, sculptures, a robotic installation, murals and other pieces around downtown.
That disagreement was largely about scale, not direction. Pittsboro’s own documents identify public art and creative placemaking as central components of its downtown strategy.
A March 2026 draft presented to the Downtown Design Committee called for a public-art master plan, integration of art into public and private spaces, permanent facilities for displaying and incubating art, and stronger connections among downtown, schools, commercial areas and gathering places. The document described creative placemaking as the deliberate integration of art and culture into land use, transportation, housing, infrastructure and economic-development decisions.
The town’s downtown work plan likewise calls for murals, storefront art, an arts corridor between downtown and The Plant, public seating, wayfinding signs and collaboration with The Plant and Mosaic. It also recommends considering land-use policies that would support walkable commercial centers and preserve the scale of Hillsboro Street near the courthouse.
Those plans confirm that Estill’s central idea is not outside Pittsboro’s official vision. The unresolved issue is whether the town and its partners will devote enough funding, property, administrative attention and political capital to make the concept visible at a regional scale.
From Rabbit Sculptures to a Missing-Letter Sign
The conversation produced several specific ideas.
One of my ideas was a series of Chatham rabbit sculptures, similar to the themed bear statues associated with New Bern. Such installations could be commissioned from different artists, placed around town and incorporated into a walking route.
Another one of my ideas was an oversized “PiTTSBORO” sign designed with a missing letter “I” so visitors could stand in the opening and complete the word for photographs.
“That is a good idea,” Estill said when the concept was proposed.
Such signs have become common tools in tourism marketing because visitors distribute the resulting images through social media. The attraction is not simply the object itself but the behavior it encourages: stopping, posing, sharing and identifying publicly with a place.
The town’s planning documents already discuss gateway installations, improved entrance signs, public-art signage, locally produced sculpture and the use of art to establish a recognizable sense of arrival. The creative placemaking draft specifically emphasizes major and minor entry points along U.S. 15-501 and U.S. 64 Business.
We also discussed the temporary nature of some artwork. Estill pointed to a large butterfly mural at the Yoga Garden and said redevelopment could eventually remove the building on which it appears.
“As what we have artified also gets deleted, that’s why you have to keep pounding on it,” he said.
His observation highlights a practical challenge. Murals can be cheaper and faster to produce than major sculptures, but they are vulnerable when buildings are sold, redeveloped or demolished. A long-term public-art strategy must therefore address ownership, maintenance, relocation, insurance, conservation and what happens when the underlying property changes.
Art, in Estill’s formulation, is not a finished project. It is a continuing public commitment.
Entrepreneurs, Public Money and the Free-Market Question
Eric agreed that beautification benefits Pittsboro but argued that the primary responsibility for attracting customers rests with entrepreneurs and individual business owners.
“At the end of the day, it is the entrepreneurs and the individual business owners to be creative and bring businesses that attract people here,” Eric said.
But is this something local businesses can do on their own?
Public agencies can build sidewalks, improve streets, revise zoning, provide grants and install artwork. They can create conditions in which businesses are easier to reach and more enjoyable to visit. But government cannot guarantee that a restaurant will serve memorable food, that a music venue will book appealing performers or that a retailer will offer products customers want.
Private businesses, meanwhile, often cannot independently finance the infrastructure, coordinated branding or public gathering spaces that make an entire district competitive.
Pittsboro’s planning documents reflect an attempt to combine those roles. The downtown work plan calls for business recruitment, coordination with private organizations, grant assistance, expanded events, business surveys, promotional campaigns and infrastructure planning.
Estill’s proposal is therefore best understood as a partnership model. A town contribution would not replace private investment. It would be one portion of a larger pool intended to produce an attraction no single small business could afford alone.
The debate is likely to intensify as Pittsboro considers how public land should be redeveloped. Art and public spaces may create broad community benefits, but they compete for funding with utilities, transportation, public safety, housing, staffing and other essential services.
The challenge is to determine which public investments will stimulate enough private activity to justify their cost.
Pittsboro and Chatham Park: Partners, Competitors or Both?
Our conversation returned to Chatham Park and Mosaic.
“I think we’re in competition with Chatham Park,” Eric said. “People don’t like talking about that, but there’s this tug-of-war.”
Estill offered a more interdependent interpretation.
“You are good for them, and they are good for me,” he said. “What we have to do is figure out how to maximize.”
Both descriptions contain elements of truth. Chatham Park provides new residents, customers, infrastructure and commercial investment. It also creates destinations that may compete with traditional downtown businesses for restaurants, entertainment, tenants and visitor attention.
Chatham Park is an approximately 8,500-acre master-planned community surrounding Pittsboro, with plans for as many as 22,000 residential units, millions of square feet of nonresidential development and large areas of open space. Its scale could dramatically increase Pittsboro’s population and alter travel patterns, retail demand and the town’s physical footprint.
Mosaic, a mixed-use commercial district associated with Chatham Park, has been promoted as an entertainment and lifestyle destination with shops, restaurants, services, offices and public events.
Downtown Pittsboro cannot compete by reproducing Mosaic on a smaller scale. Its advantage lies elsewhere: the courthouse circle, historic buildings, locally owned stores, irregular streets, established community institutions and the accumulated stories of a county seat founded in the 18th century.
The town’s official downtown vision recognizes that distinction. It calls for preserving the scale of development along Hillsboro Street, supporting active ground-floor uses, protecting historic neighborhoods and encouraging redevelopment that reinforces walkability.
The strategic question is not which district should win. It is whether the areas can function as complementary destinations connected by roads, trails, shuttles, events and common marketing.
A Major Decision Looms Over Publicly Owned Downtown Land
The sharpest planning disagreement involved the Downtown Pittsboro Public Properties project, a joint effort by the town and Chatham County to consider the future of publicly and stakeholder-owned land near the historic courthouse.
Estill criticized what he understood to be the emerging plan, describing it as focused on multifamily housing and a tall office building without adequate public parking. He argued instead for a more ambitious food, beverage and entertainment destination, potentially connected to nearby properties by a pedestrian bridge or “skywalk.”
The official project description is broader than Estill’s characterization.
According to the town, the project includes 22 properties grouped into seven sites encompassing approximately 28 acres. About 20 acres are owned by Chatham County; the remaining land is associated with the town, the Pittsboro Fire Department and Habitat for Humanity. Potential uses include housing, commercial space, civic facilities and public gathering areas.
The process is divided into three phases: community visioning, preparation of site-redevelopment concepts, and development of a partnership and implementation strategy. The stated goal is to combine public input with market analysis before identifying a preferred plan.
On July 13, one day after our lunch, the Pittsboro Board of Commissioners had a resolution supporting the project’s pre-development analysis on its agenda. Town staff recommended adoption. At the time I was putting together this article, an official town recap confirming the board’s disposition of that item had not been located.
The distinction between a planning concept and an approved development is important. The project has not simply been reduced, in its public description, to one office tower and one housing complex. Nevertheless, Lyle’s criticism raises legitimate questions about the balance among housing, employment, parking, open space, commercial activity and public ownership.
The redevelopment opportunity is unusually consequential because county departments are expected to move from several downtown properties. Once those buildings and parking areas become available, the town and county will have a chance to reshape multiple sites within walking distance of the courthouse — an opportunity that may not recur for generations.
Advisory Boards and the Question of Public Influence
Participants expressed frustration that members of downtown advisory groups had not been sufficiently consulted about the public-properties plan before it reached elected officials.
“What’s the purpose of the advisory board?” I asked.
That question has broader relevance. Advisory boards do not ordinarily possess final authority. Their role is to study subjects, gather information and make recommendations to elected bodies. Their effectiveness depends on whether elected officials and staff involve them early enough for their advice to influence a project.
Pittsboro’s Downtown Advisory Board is intended to help create, promote and sustain downtown as an economically viable business, entertainment, social and cultural center. Its committees address promotion, design, organization and economic vitality.
The July 13 commissioners’ agenda also included a proposed policy governing town advisory bodies, illustrating that Pittsboro is reviewing how those groups operate and relate to elected officials.
Our lunch discussion suggested that process can be as controversial as design. Residents may accept that commissioners have the final vote while still expecting advisory groups to review major concepts before decisions are advanced.
A strong public process does not guarantee agreement. It does, however, clarify which alternatives were considered, which concerns were raised and why a particular option was chosen.
Greenways as Economic and Civic Infrastructure
Lyle’s second major proposal was a connected greenway system stretching from Central Carolina Community College through town and toward recreation areas near Jordan Lake.
At present, he said, Pittsboro has disconnected trail segments rather than a network. He called for links to the fairgrounds, the planned park beside The Plant and other destinations.
“There are two kinds of towns in this world,” Estill said. “Cool towns — they’re the ones that have greenways — and uncool towns.”
His wording may have been intentionally provocative, but the underlying proposal is consistent with adopted town policy.
Pittsboro’s 2020 Bicycle and Pedestrian Plan identifies potential greenway connections, including a link between the Central Carolina Community College trail system and Town Lake Park. The town has also endorsed a comprehensive bicycle and pedestrian network and future greenway projects extending beyond the completed Robeson Creek segment.
The town’s parks plan recognizes social, economic, health and environmental benefits from parks and trails. Pittsboro currently lists 11 parks and recreation properties, while long-range plans envision broader connections among neighborhoods, commercial districts, schools and natural areas.
A connected trail system could also support Estill’s larger economic argument. Visitors could move among downtown, The Plant, parks and emerging developments without making every trip by automobile. Residents could reach businesses and events while gaining recreational space and alternative transportation.
The value of a greenway is not limited to the trail surface. Its success depends on where it leads, whether road crossings are safe, whether destinations provide bicycle parking and whether surrounding businesses orient entrances toward trail users.
In that sense, greenways and public art serve a similar function. Both can connect otherwise isolated places and turn travel through town into an experience.
Confederate Symbols and Pittsboro’s Unresolved Divisions
The most sensitive portion of our conversation concerned Confederate battle flags displayed on private property near an entrance to Pittsboro.
Estill argued that the flags communicate an image to visitors and complicate efforts to market the town as welcoming and distinctive. Eric acknowledged the reputational concern while emphasizing private-property and free-speech rights.
The discussion then revisited the bitter conflict surrounding the Confederate monument formerly located at the historic courthouse.
In 2019, Chatham County’s decision to remove that monument led to months of demonstrations, counterdemonstrations, arrests and litigation. The monument was taken down in November 2019 after a court dispute over ownership and the county’s authority to revoke permission for it to stand on courthouse grounds.
Greg, Eric and Lyle argued that activists on both sides sometimes came from outside Chatham County, intensifying the dispute and creating the perception that outsiders were instructing local residents how to understand their own community.
Greg said an attempted private negotiation might once have persuaded individuals associated with the flags to remove them if county officials apologized for comments interpreted as encouraging interference with private property. According to his account, the apology did not occur and the effort failed.
“If it involves shaming the people who did it, it ain’t going to happen,” Greg said.
Estill agreed that progress would require people to “put away your daggers and your old gripes.”
The exchange did not resolve how Pittsboro should respond to divisive private displays. Government cannot treat private political expression in the same manner as a monument located on public grounds. Community members, businesses and property owners can, however, engage in persuasion, counter-speech, negotiation and voluntary action.
The larger issue is whether the town can build a shared identity strong enough that no single symbol — government-sponsored or privately displayed — becomes Pittsboro’s defining image.
Wallace Kaufman and the Value of Uncomfortable Questions
An extended detour in our conversation focused on author and environmental thinker Wallace Kaufman, whom we remembered from an earlier county land-use board.
Eric recalled Kaufman challenging the seemingly uncomplicated goal of preserving rural character by asking what agriculture actually does to natural landscapes. Farms, Kaufman reportedly observed, remove existing vegetation, introduce nonnative species and alter soil and water patterns.
The point was not that farming should disappear. It was that familiar slogans can conceal complicated trade-offs.
Kaufman studied English at Duke University and later wrote books including “Coming Out of the Woods,” an account of building a home in the North Carolina forest and reassessing romantic assumptions about living in nature. He also wrote critically about environmental thought and worked on conservation issues.
We all praised his willingness to question conventional positions and suggested inviting him into a future “3 Guys from Pittsboro” conversation remotely.
This interlude was relevant to the broader discussion. Pittsboro’s choices cannot be reduced to easy oppositions: growth versus preservation, art versus infrastructure, housing versus commerce, private business versus public investment or heritage versus inclusion.
Each decision contains costs, benefits and unintended consequences. The value of people such as Kaufman is their ability to challenge the language surrounding a problem before officials rush toward an answer.
A Civic Agenda Hidden Inside the Lunch Conversation
Our lunch conversation wandered through restaurants, old cartoons, business negotiations, sculpture commissions, a giant chess set, a possible ferris wheel, Confederate symbols, greenways and downtown real estate.
Taken individually, some ideas sounded whimsical. Together, they formed a recognizable civic agenda:
Pittsboro should protect and expand locally owned restaurants and businesses. It should invest in public art at a scale large enough to attract visitors. It should connect downtown, The Plant, parks and emerging developments with greenways. It should treat publicly owned land as a rare community asset rather than simply another development opportunity. It should distinguish itself from Chatham Park while benefiting from the population and investment Chatham Park brings. And it should address historical and political divisions through conversation and negotiation rather than renewed public warfare.
None of us offered engineering studies, financial models or final designs. Nor did we agree on every role government should play.
We certainly weren’t going to be able to tackle the various issues facing Pittsboro. Our contribution over lunch was to ask whether Pittsboro intends merely to accommodate growth or use growth to build something extraordinary.
“We can sort of continue on in mediocrity,” Lyle said, “or we could go do something spectacular.”
The Next Step Belongs to the Public
Pittsboro’s official plans already contain many of the principles we discussed at Doherty’s: creative placemaking, public art, walkability, new restaurants, historic preservation, business recruitment, greenways and coordination with The Plant and Mosaic.
The harder work is deciding where those principles will be applied, how much money will be committed, which properties will remain public, how development will be scaled and whose advice will shape the final decisions.
The most important takeaway from this “3 Guys from Pittsboro” lunch may not be any particular sculpture, trail or redevelopment concept. It is that Pittsboro’s identity is still being negotiated — and that decisions made during the next several years could determine whether the historic town becomes a distinctive regional destination or an older downtown surrounded by development designed elsewhere.
Our conversation at Doherty’s was informal. The stakes were not.