Cindy Perry: ‘The One Who People Call for the Good, the Bad and the Ugly’

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Looking back on Pittsboro Mayor Cindy Perry’s career and how it led her to Chatham, the place she loves most

Cindy Perry
Cindy Perry was recognized as one of Chatham Magazine‘s 2022 Women of Achievement.

By Dolly R. Sickles | Photography by John Michael Simpson

Like her heroine Eleanor Roosevelt, Cynthia CindySax Perry leads with her heart. 

“[Eleanor] was a compassionate person,” Cindy says, “and if you can be part of the government and still be compassionate, I think that’s an amazing thing to carry out.” 

Politics have long been part of Cindy’s pedigree, and this thriving septuagenarian continues to bring vital and visible representation to the Chatham County seat during her third term as mayor of Pittsboro. She is proving that her notion of “kindness, common sense and helping people are what’s important” while “everything else is just window dressing.” 


Cindy was born in New York, raised in California and arrived in North Carolina in 1965 to attend Guilford College in Greensboro. After graduation, she worked for about 20 years as a legal secretary in Greensboro, Chapel Hill and Greenville with the dream of law school always there. “But my grades weren’t too stellar, and I played too much bridge,” she says, laughing. 

She worked with accomplished lawyers, including former N.C. Rep. Joe Hackney, a Chatham native, and U.S. Rep. David Price. It was Joe who encouraged Cindy to go to law school, but she worried about the logistics of raising three children younger than 11. “Joe said, ‘Cindy, people do a lot with three children.’ I was in my mid-30s and had been out of school for 20 years, and I couldn’t imagine [it],” Cindy recalls. 

Fortune favors the bold, and much to the delight of her children, Cindy began her journey at Campbell Law School at age 39. “The idea that their mom would go back to school was so interesting,” she says. “If for no other reason, it taught [them] that you don’t ever stop learning.” 

It was a lesson that served them well in the small Chatham community of the 1980s. “Raising children here was phenomenal,” Cindy says.” We knew the teachers; we knew the parents; we knew the other kids.” 


Cindy practiced law for 25 years before retiring in 2014 and selling her Pittsboro practice. It didn’t take long to realize she missed the people she worked with in the community, so she ran for mayor. She was elected to her first two two-year terms, serving from 2015 to 2019. 

Cindy focused on issues such as pesticides and initiatives like regulating signs and banning postings on poles to keep the town tidier. Clean water and the climate came on her radar when she was invited as a panelist to the 2018 North American Climate Summit in Chicago, representing small-town America alongside other mayors from across the U.S., Canada and Mexico.

After leaving office in 2019, she focused on other ways to serve the community. She volunteered as board treasurer for the nonprofit Second Bloom of Chatham, which provides support and resources for victims of domestic violence and/or sexual assault. Eventually, politics called her back. 

“When I ran again [in 2021], I ran on water-quality issues, because what’s in our system is already here,” Cindy says. “My heart breaks for the children of this town, having to ingest that water.” 


Cindy’s vision of the future is to bring together the new community of Chatham Park and “legacy Pittsboro” and to integrate them as smoothly as when Fearrington Village was established in northeastern Chatham in the mid-70s. 

“I was here when Fearrington Village came along, and everybody was worried,” Cindy recalls. “But what would we do without this vibrant group of volunteers who go to the school system and read with elementary children and make cupcakes and volunteer in so many places? We didn’t perish then or now. It’s been a wonderful resource for this community.” 

Cindy feels the same way about Chatham Park. “These people are going to become members of this community and are going to contribute in their own way,” she says. “Right now, it’s an us and them [mentality], but I’m looking forward to it being a ‘we.’” 


Cindy and her husband of 23 years, Dan Perry, live downtown in a historical home that provides the perfect launch pad for her adventures walking around town with her rescued chocolate Lab, Cocoa

“People will tell you they see me walking miles from home,” Cindy says. “I can pop my head into the barber shop or in Virlie’s, and I see people I know. I think I’ve been in every shop in town. The bakery puts out dog treats. People beep at me. I love it. ” 

This is the Pittsboro that Cindy adores, the one that captures her heart. She’s a woman who puts her money where her mouth is and leads by example. She’s an ardent recycler and a selfless volunteer. And as mayor, Cindy enjoys being the public face of the town and helping to establish the agenda. 

“I’m the one who cuts the ribbons and the one who people call for the good, the bad and the ugly,” she says. “I like helping people who are befuddled either by bureaucracy or their own circumstance. It’s a very sweet town. This community has more compassion and more sensitivity than any place I’ve ever lived.” 

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