Where most people see paintings and other fine arts and crafts through the windows of the Hillsborough Gallery of Arts, Alexa Chavious-Jennings sees the creaky-floored, penny-candy-stocked shop of her childhood.
“I’m sure it had an actual name, but my mom always called it the five-and-dime,” she says. “My fondest memories were going there.”
Artists and authors feel at home in this historic town, whose main street looks much the same as it did in 1914 (pictured), when the old town water pump still stood at its center. Photography courtesy of History of the Town of Hillsborough, 1754-1966 (1966) by Allen Alexander Lloyd and Pauline O. Lloyd
Chavious-Jennings could count on making the trip to North Churton Street several times a month. The youngest of nine, she knew to keep her nice footwear tucked away — those were for church, and this called for playing shoes. It was a 15-minute walk at a steady pace, but they’d often stop along McAdams Road, an offshoot of North Churton, to visit with any aunts, uncles, and grandparents who were out on their porches.
Though the street has changed through the decades, so much remains the same. Today, at 56 years old, Chavious-Jennings and her husband, Mike Jennings, still live in the cinderblock home where she grew up, and when she passes by the gallery, she can’t help but think of those visits to the five-and-dime. With family roots that go back to antebellum Hillsborough, her lineage is woven into the town’s history.
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Hillsborough has tried on several names since it was founded in 1754: Corbin Town, Childsburgh, and finally, in 1766, Hillsborough, in honor of Wills Hill, the British secretary of state for the colonies.
Soon after, the town became the center of the Regulator Movement. Farmers protested corrupt officials and unfair taxes — an early sign of the colonists’ Revolutionary fight for fair government.
Courtney Smith photograph by Alex Boerner
Courtney Smith has spent countless hours digging through records from this time, uncovering a slew of historical anecdotes and mapping businesses from past to present. It’s no small feat considering that Hillsborough’s historic district, on the National Register of Historic Places, features more than 100 buildings from the 18th and 19th centuries.
“I’m up there going down rabbit holes,” she says, nodding to her office on North Churton Street. Smith is the exhibits and programs coordinator at the Orange County Historical Museum, but her work extends far beyond that title. After moving to Hillsborough in 2020, she realized there was a gap in information about bygone businesses on Churton Street. Her commitment to research has led to an award-winning website, churtonstreet.org, that features detailed maps of businesses from 1754 to the present.
“I remember my parents taking me to the National Portrait Gallery,” Smith says. “I’d look at these portraits of people from colonial days and wonder what they would be like if they were walking around now — and I still do that.”
In her office, Smith often sits by a lunette window surrounded by archival boxes, reading old newspaper advertisements for businesses with directions like, “Start at the stone and walk toward the tree 40 paces.”
Despite the head-scratching such artifacts can cause, Smith is drawn to uncovering, bit by bit, how the buildings that enliven the heart of this historic town — the ones that live brilliantly in the memories of locals like Chavious-Jennings — came to be.
Related: Click here to find out what to see and do on North Churton Street in Hillsborough.
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