Exploring Hillsborough, North Carolina

Hillsborough, NC is one of my favorite small towns in North Carolina. The historic downtown area is bustling with people enjoying patio dining at one of the many restaurants. Parking is free and, on your walk to the shops, you’ll pass several historic houses.

It’s a historic town with plenty of things to do, rich history, and more places to enjoy the outdoors than you would think.

Shops on a street with road to the right. The stores are 2 floor brick buildings and you can make out the name "The Wooden Nickel" on the black awning of the first store.

Beyond its quaint downtown streets lined with great restaurants, and more places to walk and hike than one would expect, it also has a big part in North Carolina’s rich history

Even though I keep thinking Hillsborough is too far, I find myself there frequently. It’s less than an hour from RTP, and right around the corner from Chapel Hill.

Getting to Hillsborough and Parking

You’ll likely enter the town from one of the major highways (I-40 or I-85). As you cross over the Eno River on a small bridge, the town changes from a street lined with fast food to a quaint, historic downtown full of brick buildings from the 18th and 19th centuries.

The free covered parking deck is immediately on your left as you cross over the bridge into town, right next to Weaver Street Market.  You can see it from the bridge and there’s a traffic light to make the left. 

There’s plenty of street parking too. Take a turn down any street and you’ll find lined parking spots. If you’re lucky, you may also get a spot in the lot behind The Wooden Nickel restaurant.

Things To Do In Hillsborough, NC

There’s plenty to do in downtown Hillsborough and just outside of town.

History buffs will love the historic homes downtown. Foodies will enjoy all the great food. Outdoor enthusiasts can find short and long trails, plus there are fun ways to connect areas for crazy long hikes.

Even if you give yourself an entire day, you’ll have to come back to enjoy everything Hillsborough has to offer.

Two story farmhouse with white planks and green shutters. There's a large porch across the front of the first floor. This is an old home moved to its current location to serve as the Hillsborough Visitor Center.

Visit Historic Downtown

Downtown Hillsborough is built as a grid with South Churton Street as its main street.  The historic downtown area is small, making it easy to visit in a day.

Hillsborough is home to several buildings on the historic register. You’ll see signs outside the houses just off South Churton Street. Almost all are private homes so please don’t trespass. It’s not uncommon to see the owners tending their lawns or sitting on their porches.

It’s also fun to look up the history of the homes and buildings you pass. The Old Orange County Courthouse was built somewhere around 1844. Believe it or not, it’s still in use today for county judicial business.

Orange County Courthouse red brick building with large white pillars at the front was built in the 1800s.

A fun fact is that the visitor center is actually an old farmhouse built around 1790 that was moved to its current location. This home played a key role in the end of the Civil War. It’s an important piece of American history. I won’t spoil it, but you can learn more if you visit.

If you enjoy unique architecture, head over to W. King Street and look for the Twin Chimneys house. It’s appropriately named for the massive pair of chimneys on each side of the house. 

The twin chimneys house, a two story, white building with porch in the front on both the first and second floor. Two large chimneys are on the left side of the house from the bottom stretching to above the roof.

Find Your New Favorite Restaurant in Hillsborough, NC

For anyone that can’t function without coffee, the local coffee shop, Cup-A-Joe, is here to help you out. Many locals like to enjoy their coffee from the small tables along the sidewalk.   

Of course there’s also the local pub, The Wooden Nickel, which goes beyond being just a popular bar to being a well sought after restaurant. It can be difficult to get a table here so come early. The owners are awesome. They really strive to help the local business community.

Antonia’s is on my list to try. I haven’t eaten there yet, but the food looks and smells amazing. You can ogle the dishes from the patrons enjoying their meals on the patio alongside the sidewalk.

There’s also Saratoga Grill, a staple of Hillsborough for over 25 years. Their mission is to serve great food at affordable prices. 

View of Panciuto and Saratoga Grill on Churton Street in Hillsborough, NC.

For a more casual vibe, you can hit up Radius Pizzeria and Pub.  There’s also Weaver Street Market, a coop grocery with a great food bar, where you can load up a plate and enjoy outdoor dining.  

Two new bakeries have also popped up. Hillsborough Bakeshop and Pasta Co. is in the space where Panciuto used to be. The owners of Panciuto decided to go in a different direction where they can still offer good food, provide their staff with a living wage, and have time for their family.

Kim’s Bake Shop is in the James Pharmacy building. Kim was the pastry chef at Wooden Nickel Pub and James Pharmacy, which was owned and then closed by the same people running Wooden Nickel. Kim and Wooden Nickel entered into a partnership so she could open her own bakery. When she’s closed, the pub uses it for extra seating since the two buildings connect.

Shopping in Downtown Hillsborough

Hillsborough has several art galleries where you can shop, and often meet the artists.

Skylight Gallery on the corner of W. King Street and S. Churton Street is home to the Hillsborough Artists Cooperative.

There’s also the Hillsborough Arts Council on S. Churton Street, across from Antonia’s restaurant. They have a store front, but you can also enjoy one of the many events they sponsor.

Turn down a small street off S. Churton and you’ll find Margaret Lane Gallery in a small, white house on a street with the same name. There are monthly curated shows and rotating exhibits.

If you’re up for a little shopping, check out Matthew’s chocolates.  He has his tried and true, but also likes to experiment.

Local artist, Thomas Stevens has a gallery downtown showcasing his work. Fun fact, he was also the Mayor of Hillsborough for 12 years.

Book lovers can visit Purple Crow Books on W. King Street.  They specialize in local authors and its not unheard of to find one of our local celebrities there.

There are also jewelry and clothing stores along the main streets, too many to name them all. They’re perfect for getting unique gifts you can’t easily find anywhere else.

Go For a Walk or Hike in Hillsborough, NC

Outdoor lovers, and those needing to work off all that delicious food, will enjoy all the walking and hiking opportunities in Hillsborough.

Occoneechee Mountain State Natural Area

Occoneechee Mountain State Natural Area is part of the North Carolina State Park system with ponds for fishing, the Eno River to fish or wade in, picnic areas and great trails.

Small blue lake surrounded by brown grass and trees that have lost their leaves on the far side. In the middle of the lake is the top of a circular, metal container.

It’s main attraction is Occoneechee Mountain, the highest point in Orange County. The mountain rises around 350 feet from the river to a total elevation of 867 feet. 

In the spring you’ll walk through wooded areas and past blooming rhododendrons. If you take the Overlook Trail, you’ll be rewarded with a great view of the area below. 

While not extremely difficult, this is quite a hike and requires boots or trail runners. 

Occoneechee Speedway

The speedway has so much history, it could be its own article. I’ll just hit the highlights here. It’s one of the last dirt speedways from NASCAR’s inaugural 1949 season. Actively used for racing from 1948 to 1968, it’s now a place for hikers and joggers.

You can walk or run around the 1-mile dirt oval that used to be the track. After the track closed, the center area was used by a local high school football team. If you peek through the center of the track, you can see the old goal posts.

The podium was rebuilt and stands tall with its Pepsi sign. Beyond that, are the concrete bleachers and an old concession stand.

Old Occoneechee flag stand with Pepsi advertisement is now surrounded by trees.

There are 2 old cars along the track you can take time exploring. They’re in various states of decline but have some great history.

Outside the track are additional trails that circle the entire area. One comes close to Ayr Mount below.

Ayr Mount

Ayr Mount is an old Federal style plantation that sits on 503 acres. Most of the land was left on its own and not farmed. 

While you can tour the home, the main attraction here is the Poet’s Walk, a one-mile trail circling the grounds that serves to inspire writers and artists. 

The walk will take you past the house, through sparsely wooded areas, and around a pond. In many places it circles large spans of inviting green lawn, just begging you to sit and stay a while.

The Poet’s Walk comes close to the trails that circle around the Occoneechee speedway. A few savvy insiders know how to link the trails by crossing the river so don’t be surprised if you see someone that appears to be walking out of the woods. 

Parking is free, but it can get crowded in the evenings so come early.

The River Walk

Many areas of North Carolina have a greenway and Hillsborough calls its greenway the River Walk.  It officially starts at the Occoneechee village replica and ends at Gold Park, but there’s an additional trail on private property that continues the walk down to the Occoneechee speedway. 

From Gold Park to the Occoneechee village replica is around 1.8 miles.  If you take the private trail and continue to the speedway, the entire trail is around 3 miles one-way. 

Wooden boardwalk with a metal rail for safety. One sign notes Gold Park is to the right and another notes River Park is to the left.

For the most part, the River Walk keeps you close to the Eno River. You’ll wind around and over it as it moves from your left to your right in a windy, relaxing setting. The trail is paved making it perfect for pushing a stroller, walking, and running. 

Used by locals for morning or evening walks, you’ll see people sitting on the benches watching their children play near the water, or just taking a break to enjoy the fading sun. 

It’s a wonderful way to relax while also enjoying some unique sights. 

Since it goes right past Weaver Street Market, you can also stop and grab something to eat or a drink.

Eno River State Park

While technically in Durham, Eno River State Park is fairly close to Hillsborough. If you drive straight down highway 70, you’ll pass right by the Pleasant Green intersection. Make a quick left and the Pleasant Green access is less than half a mile on your left.

Continuing down the road, you’ll come to the large intersection with Cole Mill Rd. A quick left here will take you to the main entrance of the park, home to Cox Mountain Trail with the famed suspension bridge.

The suspension bridge at Eno River is long and narrow and can be scary. It's a wooden bridge wide enough for one person with wire ropes on either side.

Eno River is a popular park for hiking and playing in the water during the summer.

There are miles of trails accessible from three main entrances. Online, you can also find trail access with parking outside the park. 

Festivals in Hillsborough

Hog Day

The big event Hillsborough is known for is the Hog Day BBQ Festival usually held in September.

North Carolina is known for its BBQ and you’re in for a treat as this festival features the best NC pulled pork available. There’s also live music, vendors with handcrafted gifts, and lots of fun for the kids. 

It’s usually held in River Park which is the large lawn on the other side of Churton Street, across from Weaver Street Market.

Art in the Heart of Hillsborough

Every April, there is an Arts and Crafts show downtown on the lawn behind the Visitors Center. Everyone is welcome. They have vendors, music, food, drinks, and plenty of art.

Solstice Celebration Lantern Walk

This is a beautiful event held in December. Attendees create their own paper lanterns and the group walks along the Eno River to celebrate the solstice.

A Little History About Hillsborough

To truly enjoy Hillsborough, it helps to know a bit about its history.

Hillsborough is actually one of the oldest towns in North Carolina, founded in 1754. It played many small, but important roles in the Revolutionary and Civil wars. 

It’s not a fluke that it sits along the Eno River. The city was built along the Great Indian Trading Path where it crossed the Eno River. Indian tribes, such as the Occaneechi and Eno lived in the area and were noted by European visitors in 1701. 

In the 1980s, an archaeological team from a local university excavated a historic Occaneechi village. A replica of the village was built close to the original site and is still standing.

Replica of the Occoneechi Village. Three large grass huts in a semi circle. They are inside a fenced area.

Hillsborough was where the first North Carolina ratifying convention was held to determine whether to ratify the Constitution recommended to the states. They chose to neither ratify nor reject it in the hope of pushing the incorporation of a Bill of Rights.

When it was finally signed, William Hopper became one of the state representatives that signed the Constitution. He was from Hillsborough and was buried here.

Is it Hillsborough or Hillsboro?

Let’s address the elephant in the room. How the heck do you spell the town’s name? It turns out there’s a bit of interesting history on this one.

The original name of the town was Hillsborough, but it was shortened to Hillsboro during the 19th century. 

Residents voted to change it back to the original spelling in the late 1960s.

So it is technically Hillsborough, but I’ve seen the shorter version from time to time. Google says it’s Hillsborough and they always have the final word.

Just because it’s fun, here’s some additional history on the naming of Hillsborough.

When it was founded in 1754, the town was called Orange in honor of William III of the House of Orange. But since it was located in the center of Orange County, this created a lot of confusion.

To alleviate confusion, the name was changed to Corbin Town (or Corbinton) in honor of Francis Corbin. But this didn’t last long, and by 1759 it was changed again to Childsburg to honor Dr. Thomas Child.

The final name of Hillsborough was assigned in 1766 to honor Will Hills, the earl of Hillsborough. 

That’s four names and one spelling change for this little town.

White sign in front of a house noting this is a historic building that was home to the Cole Hotel. Behind it in the distance is another sign for another historic home. There are many of these throughout the downtown area.

Wrap Up: Hillsborough, NC

Since I’m frequently out and about exploring North Carolina, I try to push people to check out their local towns and see what’s around. It’s surprising how many fun and unique opportunities are less than an hour away. Hillsborough, NC is a great example of this.

From some of the best restaurants in the area to shopping for that perfect gift to wandering through neighborhoods with historic homes, there really is something for everyone.

For a small town, it’s a bustling place. Even on weekdays, you’ll find plenty of people enjoying sidewalk dining on the small restaurant patios. The vibe is low key fun. You’ll see people with their dogs, couples enjoying a night out, and a group of friends having a round of beers at the Wooden Nickel.

If you only have a day and are looking for a new place to visit, Hillsborough is it.

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