Related: Click here to read about historic North Churton Street in Hillsborough.
Antonia’s
This restaurant serving handmade pasta and cocktails was once home to the first state treasury before it moved to Fayetteville in 1789 and then Raleigh in 1795. Then, it aided in transferring another kind of asset: hooch. In the basement, there’s still a Prohibition-era tunnel the width of a five-gallon bucket rumored to branch out to each corner of the street above.
(919) 643-7722
antoniashillsborough.com
Kim’s Bake Shop
A circa-1940s James Pharmacy sign welcomes guests to a shop stocked with an ever-changing selection of doughnuts, cookies, and more. The mint-colored tile floor is original to the pharmacy, along with the backbar mirror promoting Dr Pepper behind rows of mugs and coffee presses.
(919) 265-4988
downtownpies.com
Wooden Nickel Pub
Next door, this local favorite — which sources much of its meat from its own farm — serves up burgers, wings, and unexpected specials, like pot roast grilled cheese. The walls are collaged with photos of employees and patrons, and the standing bar is carved with the names of regulars from over the years.
(919) 932-0134
thewnp.com
Orange County Historical Museum
Over nearly two centuries, this lot held a burial ground, two churches, a schoolhouse, and the town library — the stone building we see today, where experts have shared artifact-based storytelling since the early 1980s.
(919) 732-2201
orangehistorync.org

Old Town Cemetery photograph by Alex Boerner
Old Town Cemetery
Intricate headstones mark notable local figures and families at one of the state’s oldest municipal cemeteries. Founded in 1757, the burial ground is where esteemed brickmason John Berry and William Hooper, a signer of the Declaration of Independence, lie in rest.

Burwell School Historic Site photograph by Alex Boerner
Burwell School Historic Site
Docent Carol McCanna guides visitors around this 1821 site, where the Burwell family started a school for girls. Diaries recount schoolhouse routines, furniture showcases the work of free Black cabinetmaker Thomas Day, and a storyboard shares the experiences of Elizabeth Keckley, an enslaved young woman who worked for the Burwells and later bought her freedom.
(919) 732-7451
burwellschool.org
Hillsborough Arts Council
HAC has been a cornerstone for creatives for decades, organizing events like the Art Walk and makers’ markets. Its gallery and gift shop features pieces from more than 60 local artists.
(919) 643-2500
hillsboroughartscouncil.org
Matthew’s Chocolates
Before going in to choose a truffle, look for a faint carving reading “Hillsboro Branch” and a bank deposit box. These are the last vestiges of a bank before the General Assembly reinstated the “ugh” at the end of the town’s name in 1965.
(984) 245-9571
C3 Hillsborough
A subtle sign of this coworking space’s past life is around back: An outline in the brick shows where an elevator used to transport goods at The Bazaar, one of the state’s largest department stores in the late 1900s.
c3hillsborough.com
Around the Corner
Yonder: Southern Cocktails and Brew
Enjoy literary events and live music in a cozy lounge.
114 West King Street
(919) 283-2368
yonderbarnc.com
The Colonial Inn
Stay the night at this 1838 inn featuring an original staircase and reclaimed wood.
153 West King Street
(984) 789-4455
colonialinn-nc.com

photograph by Alex Boerner
Carlisle & Linny Vintage Jewelry
Browse a curated collection of jewelry from the 1800s through the 1970s.
112 South Churton Street
(917) 400-9800