Exploring Hillsborough, North Carolina

I found myself in nearby Hillsborough, NC for almost 2 weeks and was worried it would be boring. It’s one of those local cities that you say “eh, there’s nothing there”. And it’s a little too far to just “go see”.

In short, it somehow got on the “boring little town” list.

Well, I was wrong. 

Beyond its quaint downtown streets lined with great restaurants, and more places to walk and hike than one would expect, it also has a rich history. 

On top of that, it offers free on-street parking and a free parking deck. This won me over as I am a huge fan of free parking.

Is it Hillsborough or Hillsboro?

Before we dive in, 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.

Things To Do In Downtown Hillsborough

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

You’ll likely enter the town from one of the major highways. As you cross over the Eno River on a small bridge, the town changes from a small highway 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 your 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.  

Tour the Historic Buildings

Hillsborough is home to several buildings on the historic register, many of which you can visit using online maps. While they do offer guided tours of the city, it’s fairly easy to get around on your own.

Click here to get an online map and information for a self-guided walking tour.

Take a moment to look up the history of some of the buildings you’re viewing. The Old Orange County Courthouse was built somewhere around 1844. Believe it or not, it’s still in use today for county judicial business.

The visitor’s center is actually an old farmhouse built around 1790 that was moved to its current location.

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. 

Restaurants and Shops

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.  

One of the best Italian restaurants in North Carolina, Panciuto, is located right on Churton Street. My New York Italian parents, who rarely eat at Italian restaurants (because let’s face it, no one makes Grandma’s sauce), think it’s amazing which is high praise.

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.  

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

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

There are also jewelry and clothing stores along the main streets. 

The Outdoor Life

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

Occoneechee Mountain State Natural Area

The natural area is a North Carolina State Park with ponds for fishing, the Eno River to fish or wade in, picnic areas, and great trails.

Its 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. 

If you’re an avid hiker, or a local backpacker looking to do some training, this is your spot. Occoneechee Mountain Loop Trail is the main trail, with Chestnut, Brown Elfin Knob, and Overlook trails branching off for additional mileage. 

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. 

There’s also the old quarry which is fun to check out. 

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.

The 1-mile, dirt oval is still there and you can walk around it to get in as many miles as you like. If you peek through the center of the track, there are the old goal posts from a local high school that used the area for their football games.

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

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.

The Mountains to Sea Trail, an 1175 mile trail that crosses North Carolina, leads through the area, noted by the white circle blaze. It’s most prominent as you move from the parking lot to the track.

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 awhile.

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 here, it’s called the River Walk. It officially starts at the Occoneechee village replica and ends at Gold Park, but there’s a trail on private property that continues the walk down to the Occoneechee speedway. 

From Gold park to 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. 

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. 

Beautiful bridges help you crisscross the river at the many crossings. At one point, a small, covered bridge takes you under a set of working train tracks. 

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 not exactly in downtown, 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 park 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.

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. 

Want to get away for the night? Campsites requiring about a mile of hiking to reach are available. You’ll need to reserve them ahead of time. Piper Creek Campgrounds are an easier hike on a flat trail. The Fanny’s Ford sites are great, but you’ll need to climb down a hill using steps (and then up on the way back).

Events 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.

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.

Hillsborough – Give it a Try

I always push people to check out their local towns and see what’s around. Travel doesn’t have to be some large trip you save for and take a week of vacation time. 

Often there are great things right around the corner that you can visit and enjoy on a weekend. Taking the time to see something new, relax and hit the week feeling recharged.

Sometimes I need to be reminded to follow my own advice. This time, I’m glad I took the time to get to know Hillsborough. I know there’s more this small town has to offer. 

Articles You May Like

Click to Share

5 Responses

  • I grew up in Hillsborough, there weren’t any parking decks. It was Orange Speedway not Occaneechi Speedway. There werent any Restaurants downtown. No hiking trails. On Highway 70 was Jacks Snack Shack. And when Tastee Freeze came everyone was happy. Latter The Daniel Boone was built.
    The only thing we had was Bobby Crawfords Skating Rink, he had two of them. We rode our bikes all over town, played in the Eno River. If you lived out in the country you played in the yard or woods. The town drunks hung out by the old Depot in West Hillsborough across from Ira Peeds grocery store. He had delivery service. Thats the Hillsborough my cousins, friends grew up in.

    • It’s odd to see how much it’s changed over the years. I grew up in a small town in NY that’s now apparently pretty big. When we got a KFC it was a HUGE deal. That was the only fast food restaurant for years and it seemed so “big city”. One thing I like about Hillsborough is that some of the neighborhoods still have a lot of land. The houses sit on an acre or two which is something you rarely see anymore in NC.

      Thanks for sharing!

    • That’s the Hillsborough I remember as a child too. I would only add the delightful aromas & well dressed patrons that emerged from the locally owned Colonial Inn.

  • Wow, great article Alison! I was born and raised in Hillsborough, now live in Hillsborough with my husband, and I also work with the Alliance for Historic Hillsborough, and I think you did a fabulous, accurate job of summarizing a lot of the highlights of the town. Thanks for taking the time to do so!

    • Oh wow, Amanda. Thank you so much for taking the time to write a comment. I’m so glad you liked the post. I was pet sitting out there and thinking there was nothing to do until I got over myself and realized I wasn’t giving Hillsborough enough credit. It truly is an amazing town and I’m glad I learned more about the history.

Leave a Reply

Your email address will not be published. Required fields are marked *