7 Hours in Hillsborough

(By Charlotte Wray)

Five years ago, Hillsborough wasn’t on most people’s radar. It was, instead, a well-kept secret, shared among its six thousand residents—those who understood what made it special. That charm, quaint yet not frozen in time, is a little better known now, but it hasn’t gone anywhere. 

Hillsborough is a historic place. It was where North Carolina declined to ratify the Constitution in 1788 because it had no Bill of Rights. (The state did so, a year later in Fayetteville, after the Bill of Rights was added.) But Hillsborough also has an artistic flair, a vibrant culinary scene, and was declared “America’s Little Literary Town” by The Wall Street Journal, which, I suppose, is better than the alternative. 

If you’re here for a day, even a few hours, you’ll get a sense of why we love Hillsborough. Start early, say, 7:00 a.m.—the town is perfect on an autumn morning, even a Monday. Begin at Cup A Joe, where you see neighbors chatting before work and children munching on muffins before school; there’s also a comic book rack and Stranger Things trading cards in front of the register. This is quintessential Hillsborough: quirky, amusing, talkative, neighborly, small. Check out the homemade pastries: The jalapeño cheddar biscuits and black cherry pistachio biscotti are at the top of my list. 

When you’re sufficiently caffeinated, the best way to get to know Hillsborough is on foot. 

The Old Orange County Courthouse is the town’s epicenter. Atop it is a regal, eighteenth-century clock that, if it could tell tales, might reveal whether or not it was a gift from King George III, and whether the legend of its short swim in the Eno River is myth or reality. 

Continuing your walk up Churton Street takes you to the Burwell School Historic Site. Last year, the site of the nineteenth-century school for girls honored the two hundredth birthday of Elizabeth Hobbs Keckley, an enslaved woman who, once freed from the Burwell family, became Mary Todd Lincoln’s modiste and closest confidante, then wrote a tell-all about her time in the White House. 

A stone’s throw from the Hillsborough Visitors Center—which is also the relocated Alexander Dickson House, is Ayr Mount, a Federal-era plantation house built in 1815. It’s very grand and most beautiful around the holidays.

After a morning of historic meandering, a sandwich is necessary. Steve’s Garden Market has you covered for the perfect BLT, best eaten on a bench along the Riverwalk. There you can also see a replica of the seventeenth-century Occaneechi Village, once home to the tribe that originally lived on the banks of the Eno River. (The Occaneechi abandoned the Eno River Valley by 1712, after suffering from Iroquois war raids and European diseases.)  

As you might imagine, it’s difficult to see every historic hotspot in Hillsborough in a day, but you can take the town’s history with you. 

Duck into local bookshop Purple Crow Books to see both the history and talent Hillsborough possesses. An entire wall is dedicated to local authors, including nationally recognized and best-selling authors such as Lee Smith, Jill McCorkle, and Allan Gurganus. Take a trip to Italy through the eyes of part-time Hillsborough resident Frances Mayes, author of Under the Tuscan Sun, or pick up award-winning journalist Steven Petrow’s renowned guide on LGBTQ etiquette, Complete Gay & Lesbian Manners: The Definitive Guide to LGBT Life.

That’s just the beginning—and it’s only two o’clock. You still haven’t hit up The Wooden Nickel or had dinner at Panciuto or drinks at Yonder.  

In Hillsborough, greatness is tucked into the corners, absent pretentiousness. One can rub elbows with any of these authors at Cup A Joe or walk before in front of a building without knowing its significance. 

This is why people keep coming back: No matter how small the town, you never run out of new things—and people—to discover. 

Landmark: Colonial Inn

Where to Get a Cup of Coffee: Cup A Joe

Where to Visit with Friends: The Wooden Nickel

Where to Walk Your Dog: Occoneechee Mountain State Natural Area

Where to Spend the Night: The Inn at Teardrops



110 South Churton Street, 919-732-6261, panciuto.com

Chef Aaron Vandemark enjoys no shortage of well-deserved accolades. At Panciuto, the perennial James Beard semifinalist explores Italian cuisine with Southern ingredients from local farmers. The menu changes with the seasons and Vandermark’s whims—seriously, it changes all the time—but be sure to try the homemade pastas and the sublime vegetable board.

Note: We’ve highlighted our pick for the best of each category below. 



101 North Churton Street, 919-643-7722, antoniashillsborough.com

With a stamp of approval from Under the Tuscan Sun author Frances Mayes, this Italian eatery isn’t just authentic, it feels like eating at your nonna’s house. Antonia’s bustles in the evening, serving mounds of homemade pasta. Sit outside and take in the charm of historic Hillsborough over a plate of spaghetti all’Antonia.

El Restaurante Ixtapa

162 Exchange Park Lane, 919-644-6944, ixtapa.homestead.com/homepage.html

Two generations of the Munoz family chip in at this family-run shop, which features tacos with handmade tortillas. 

Hillsborough BBQ Company

236 South Nash Street, 919-732-4647, hillsboroughbbq.com

Perfectly smoked Southern ’cue cooked over a wood-fired pit and done right, served in a relaxed atmosphere with local brews and no attitude. While brisket and ribs may not be typical of an N.C. menu, they can easily steal the show. And don’t miss the catfish or, better yet, the pork nachos, because what could be wrong about anything smothered in cheese sauce?

The House at Gatewood

300 U.S. Highway 70, 919-241-4083, houseatgatewood.com

At the end of a long driveway, nestled in a tight vignette of oak and magnolia trees, this historic home invites family and friends into an intimate experience. Once the estate of Dr. Joseph Gatewood, it’s now a place to gather for elevated Southern barbecue fixins in what they call a chophouse and oyster bar. 

J&F Kitchen

155 Mayo Street, 919-245-8463

Be sure to get a made-from-scratch pizza at this hole-in-the-wall run by a husband-and-wife team. Our favorite is the Barbecue Chicken. 

James Pharmacy

111 North Churton Street, 919-932-0134, jphillsborough.com

This eclectic seafood joint can heal a craving for a cocktail or a dozen chilled oysters. Chow down on anything from the catch of the day to the “Big Ass Bucket of Mussels,” which have been steamed in gose beer butter broth.

Jay’s Chicken Shack

646 North Churton Street, 919-732-3591, jayschickenshack.com

Wings. Burgers. Chicken sandwiches. … Breakfast? This unassuming joint off of Highway 70 is full of surprises and, most important, flavor. There’s no better place in Orange County to satisfy that wing fix—and be sure to score some fresh biscuits. 

Pueblo Viejo Mexican Restaurant

370 South Churton Street, 919-732-3480

Fresh ingredients, classic Mexican recipes, and fast, friendly service equal a perfect spot for that late lunch that screams for a couple of quick margaritas. 

Radius Pizzeria & Pub

112 North Churton Street, 919-245-0601, radiuspizzeria.net

A fun, vibrant neighborhood hang with a funky vibe, Radius offers eclectic pizzas and a pick-your-pasta option. 

Saratoga Grill

108 South Churton Street, 919-732-2214, saratogagrill.com

Some places are affected by neither time nor tide, and you can count the Saratoga Grill among them. As businesses on Churton have come and gone, Saratoga stands, serving New England clam chowder and crab cakes. 

Steve’s Garden Market & Butchery

610 North Churton Street, 919-732-4712, stevesgardenmarket.com

For small-town natives, growth is oftentimes analogous to longer lines, construction, and traffic. But Steve’s Garden Market, a simple corner store, reconciles the new with the beloved. You can grab a pimento cheese sandwich at noon, but it’s also a one-stop-shop for any dinner. A date night is best: all the fixings for a charcuterie, local grass-fed beef steak, herbs and vegetables, and a selection of N.C. wines.

Tacos Los Altos 

126 West King Street, 919-241-4177, facebook.com/tacoslosaltos123

Once a food truck, this King Street brick-and-mortar started serving breakfast and lunch until 3:00 p.m. Sunday through Wednesday so the sibling owners could be with their families in the evening. They’ve got both Mexican and American breakfast options, everything from pancakes to enchiladas. Thursday through Saturday, they’re open until 8:00 p.m. for dinner.

The Village Diner

600 West King Street, 919-245-8915, facebook.com/villagedinernc

From its heyday in the mid-seventies to when new owner Joel Bohlin took ownership in 2017, this unassuming diner was a staple for blue-collar workers and politicians alike. Bohlin, who once managed Hillsborough BBQ, breathed new life into the place, bringing in a wood-fired pizza oven and giving it a facelift. Don’t worry; you can still cop biscuits and gravy for breakfast.

Vinny’s Italian Grill & Pizzeria

133 North Scottswood Boulevard, 919-732-9219, vinnyshillsborough.com

It’s easy to miss if you aren’t looking for it, but then you’d never know about Vinny’s buffalo chicken sub. 

Whit’s Frozen Custard 

240 South Nash Street, 919-245-8123, whitscustard.com

Whit’s defines itself by two things: fresh custard and three flavors: vanilla, chocolate, and Whit’s special weekly flavor. Blend these flavors with any of the toppings to make a “Whitser,” a decadent experience, atop a waffle cone. 

The Wooden Nickel Pub

113 North Churton Street, 919-643-2223, thewnp.com

That this restaurant is always bursting at the seams is indicative of only one thing: food and drinks done right, with one of the best burgers in the Triangle and a wide selection of draft and bottled beers.


Botanist & Barrel Winery and Tasting Room 

105 Persimmon Hill Lane, Cedar Grove, 919-644-7777, botanistandbarrel.com

What started with fermentation experiments turned into a full-fledged cidery tucked into rolling farmland on the outskirts of Hillsborough. The tasting room is located at the farm from which the cidery gets its fruit. Grab a Collusion Tequila Barrel Aged Cider or the cider dubbed Apple on the Hops.

Cup A Joe

112 West King Street, 919-732-2008

One of the greatest improvements to Hillsborough in a century happened when Cup A Joe moved to larger digs. But even after it traded cramped quarters for a larger space, there still never seems to be an open table. Credit this to the experienced baristas and the chill vibe. 

Hillsborough Wine Company

118 South Churton Street, 919-732-4343, chapelhillwinecompany.com

Drop into this quaint little shop for hand-selected boutique wines. Don’t know any of the labels or vintages? No problem. The employees have that covered. If their extensive knowledge isn’t enough, treat your taste buds to a one-, two-, or four-ounce pour from the wine-tasting machine.

Hot Tin Roof

115 West Margaret Lane, 919-296-9113, hottinroofbar.com

Looking for the perfect honkytonk to swill your longnecks and take in some live music? Look no further. 

Yonder: Southern Cocktails and Brew

114 West King Street, 919-283-2368, facebook.com/yonderbarnc

Boozy slushies and a bevy of brews—what’s not to love? Located in “colonial AF downtown”—as Yonder describes it—this brand-new hometown haunt has you more than covered on drinks and entertainment. There’s something going on every night, from board games to live music to stand-up comedy to pub-quiz nights.


Carlisle & Linny Vintage Jewelry

112 South Churton Street, 917-400-9800, facebook.com/carlisleandlinny

If you thought brooches were out of style, think again. Curated by owner Lindsley Bowen, this vintage jewelry shop is all the best parts of a thrift shop, offering a variety of one-of-a-kind and classic throwback jewelry, sunglasses, cufflinks, brooches, and accessories—and if you’re lucky, a glimpse of shop dog Tucker.

Eno River Farmers Market

144 East Margaret Lane, enoriverfarmersmarket.com

Boasting the same (approximate) location for over 264 years, this farmers market was one of the original structures laid out by colonial city planners. It operates year-round on Saturdays and features products from the region’s top farmers and culinary craftspeople. 

Matthew’s Chocolates

104 North Churton Street, 919-732-0900, facebook.com/matthewschocolates

In a town filled with culture and artists, you have to wonder if there’s anything more elegant than Matthew Shepherd’s chocolate creations. Be sure to stop in during the winter holidays to stock up on homemade marshmallows and hot chocolate.  

My Secret Closet

107 John Earl Street, 919-732-1254, mysecretcloset.com/hillsborough

You never know what you’re going to find at this consignment superstore. From home furnishings to home décor, My Secret Closet is a treasure trove for bargain hunters.

Purple Crow Books

109 West King Street, 919-732-1711, purplecrowbooks.com

Owner Sharon Wheeler must have the cushiest job in all of Orange County. If she needs inspiration for her recommendations, she only has to look down the street. With authors like Lee Smith, Hal Crowther, Jeffrey Deaver, Jill McCorkle, and Allan Gurganus as neighbors, who better to deliver the skinny on what’s great to read? 


125 East King Street, 919-644-8000, uniquitiques.com

The whole place is draped in vintage, from the homey décor to the curated style of contemporary women’s clothing for sale. You’ll find it all here: cowboy boots, costume jewelry, and Southern-made t-shirts. 

Volume Hillsborough

226 South Churton Street, 919-643-2303, volumehillsborough.com

It’s hard enough to find a decent record store, but can you imagine trying to score some decent vinyl while sipping on some good local suds? If so, you must have stopped by Volume Hillsborough. Belly up to the bar, order a pint, then finger your way through the vast selection of music. 

Weaver Street Market

228 South Churton Street, 919-245-5050, weaverstreetmarket.coop

Nowhere near as expensive and with a much better selection of local goods, Weaver Street is Orange County’s answer to Whole Foods. This organic grocery and co-op also provides delectable baked goods and specialty items, as well as a one-stop-shop for local brews.


Ayr Mount

376 St. Marys Road, 919-732-6886

This Federal-style plantation house, built around 1815 by William Kirkland, is now a publicly accessible historic site sitting on 265 acres, owned and operated by the Classical American Homes Preservation Trust. Aside from the well-preserved interior, the real stars of the show are the extensive scenic trails that wind across the grounds and the beautiful array of Carolina flora. 

Blackwood Farm Park

4215 N.C. Highway 86, Chapel Hill, 919-969-8959

Located on 152 acres of land between Hillsborough and Chapel Hill, this gorgeous property offers a hiking, fishing, and picnicking paradise. Be transported back in time with original structures like a historic farmhouse, barn, and smokehouse. It’s only open on the weekends, but the best opportunity to check it out may be the annual Orange County Localfest, which pops up at the end of September. 

Hillsborough Gallery of Arts

121 North Churton Street, 919-732-5001, hillsboroughgallery.com

Owned and operated by local artists, this gallery will make fans of modern and contemporary fine art feel right at home. Be sure to check in every Last Friday, when a featured exhibit highlights three of the gallery’s artists. 

Hillsborough Riverwalk

Nash and Kollock Streets, 919-732-1270, hillsboroughnc.gov

Walk off some of the satisfying Churton Street fare on the paved urban greenway stretching nearly two miles along the Eno. Walkers, joggers, and cyclists alike enjoy natural views of the lazy river and its wildlife. Vistas alongside Gold Park and River Park offer plenty for your ’Gram, but be sure to catch the star attraction: “A Sight to Behold,” the original Stickwork sculpture by Patrick Dougherty. 

Historic Occoneechee Speedway

320 Elizabeth Brady Road, historicspeedwaygroup.org

In the nineteenth century, Julian Carr raced horses here. In 1949, it became one of the first two NASCAR tracks in existence. After closing in 1968, it lay fallow until this century, when walking trails were built. There are still old and busted race cars on the grounds. 

Occoneechee Mountain Natural Area

625 Virginia Cates Road, 919-383-1686, ncparks.gov/occoneechee-mountain-state-natural-area

Hike among the rhododendron and mountain laurel. The three-mile trail follows riverside thickets and rocky bluffs as it ascends to the highest point in Orange County. 

Occaneechi Village Replica Site

East Margaret Lane, along the Riverwalk

Three hundred-plus years ago, before Hillsborough was Hillsborough, it was the ancestral land of the Occaneechi Band of the Saponi Nation. Along came Europeans, and, well, between raids by Iroquois and disease, the Occaneechi abandoned the Eno for the protection of the Virginia colony by 1712. (Most merged with other tribes and lost their tribal distinctiveness by the mid-eighteenth century, though in 2001, North Carolina recognized a small group in Orange and Alamance Counties who claimed descent from the Occaneechi.) To honor the seventeenth-century Occaneechi village, tribe members and local volunteers have rebuilt a palisade and hand-crafted huts along the banks of the river, a site you can see on a stroll on the Riverwalk. 

Old Town Cemetery

North Churton and West Tryon Streets

Located just outside St. Matthew’s Church, the cemetery was established in 1757. Its 184 marked graves (and several more unmarked) include some of the town’s most notable early residents, among them a governor, a U.S. senator, a Confederate senator, and a signer of the Declaration of Independence. 

Orange County Historical Museum

201 North Churton Street, 919-732-2201, orangenchistory.org

All you need to know about Orange County can be found in the former Confederate Memorial Building. Here, artifacts of rural life, featuring colonial weights and measures, memorabilia from different Carolina eras, and portraits of prominent Orange County figures are on display.

Orange County Sportsplex

101 Meadowlands Drive, 919-644-0339, trianglesportsplex.com

If you can imagine it, it happens here, and all indoors: swimming, ice skating, league play, sports classes, lessons, you name it. The access to the Olympic-size swimming pool alone is worth the monthly membership fee.

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