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Hillsborough: 5 Fun Things to Do, Food, History (and Why We Love IT!)

Last Updated on May 4, 2020

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Hillsborough in Orange County is among our favorite communities to visit in the Research Triangle. Its historic importance in the form of markers and buildings becomes clear to visitors and residents, but the town is also working to preserve and prop up reminders that people used this area long before Europeans arrived.

There are plenty of opportunities to learn more about the area’s background, along with a whole variety of things to do in this awesome small town. Our look inside Hillsborough will show you why this place features on our NC bucket list and why it belongs on yours, too!

Hillsborough also featured in our guide to Day Trips from Raleigh, Durham, and Chapel Hill. This post is part of our series on Orange County and all the awesome places to visit in Central North Carolina.

Hillsborough NC Background

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Hillsborough has long been known as a central location for trading. The Great Indian Trading Path crossed over the Eno River here for centuries before European arrival.

The Occaneechi and Eno were the last known Native Americans who lived in the area. Today, a replica of an Occaneechi farming village that was excavated by UNC in the 1980s can now be seen along the Riverwalk.

It was founded as Childsburgh in 1754 by William Churton and during the Revolutionary War, Hillsborough remained a significant trade spot. The town also briefly served as North Carolina’s state capital when New Bern, our first permanent capital, was held by the British.

Hillsborough is still the center of government in the area, as it’s the Orange County seat.


Hillsborough sits in Orange County and is accessible via I-85 near Durham and I-40 near Chapel Hill. US 70 and NC 86 also run through here as part of the Colonial Heritage Byway, one of our favorite scenic road trips. Those options make traveling to Hillsborough perfect for folks who prefer backroads or the more direct interstate.

Things to Do in Hillsborough NC

The Riverwalk

Things to Do in Hillsborough NC Riverwalk Image

The Riverwalk in Hillsborough is easily one of our favorite things to do, especially during cool mornings. The paved walkway snakes the Eno, lined with informational placards that detail the waterway’s importance and the life that thrives here.

It’s a little under two miles long and runs from Gold Park on Dimmocks Mill Rd downtown. The path is even part of the Mountains-to-Sea trail that runs across North Carolina.

While the Riverwalk is paved and accessible, it’s not continuously flat, so keep that in mind. We recommend parking either at Gold Park and enjoying the playground first or entering from downtown after picking up a coffee from Weaver Street Market.

We included the Riverwalk and a few more Hillsborough paths in our guide to hiking near Raleigh, Durham, and Chapel Hill!

Occoneechee Mountain State Natural Area

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Occoneechee Mountain State Natural Area might be a rather small state park-managed site at about 190 acres. But it’s a fantastic change of pace from the comparably flat terrain of Central North Carolina. The park’s ponds and proximity to the Eno River offer visitors a place to fish, too.

The actual mountain’s peak is said to be the highest point between Hillsborough and the coast. From there, you’ll find views down below and plenty of mountain laurels and rhododendrons along the way. When the trees are bare in the winter and early spring, you can even get a glimpse at downtown Hillsborough from above.

Walk the Trails at the Occoneechee Speedway

Hillsborough NC Occoneechee Speedway Image

Not just North Carolina history, but racing heritage lay tucked away along the Eno River.

Hillsborough’s Occoneechee Speedway was NASCAR’s first Superspeedway and considered one of the most dangerous tracks, too. The dirt track drew crowds of over 15,000, with legends like Fireball Roberts, Richard Petty, and NASCAR’s first female driver, Louise Smith speeding down it.

Today, the speedway has been turned into hiking trails and remnants remain from its former life. Walking the paths is a wonderful outdoor thing to do in Hillsborough.

Take a Poet’s Walk at Ayr Mount

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Ayr Mount was considered one of Central North Carolina’s finest homes when construction completed in 1812. However, this is not the typical grand house you would expect from a plantation home.

William Kirkland built it and named the home after his birthplace of Ayr, Scotland. Take a guided tour of the house between March and December and you’ll find the inside quite luxurious.

Another way to enjoy the beauty of the property is to stroll the mile-long loop, known as the Poet’s Walk. You’ll pass through the woods, along the Eno River, and through the Kirkland family cemetery. This path makes it easy for one to get lost in the beautiful surrounding scenery.

Last Friday Art Walks

Hillsborough NC Street Sign Image

With more than seven independent art galleries and an active arts council, browsing for local art is definitely a fun weekend thing to do in Hillsborough! You can go even further by partaking in their Last Friday Art Walks.

During this monthly event, keep an eye out for special artist exhibitions. Start at the Hillsborough Arts Council store for a guide to all the town’s galleries.

Restaurants in Hillsborough

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Hillsborough might be a small town but its collection of restaurants have a little something for all palates. We typically start on Churton St with Wooden Nickel, a place with a laid back pub vibe that emphasizes local brews and eats. Next door, you’ll find delightfully fresh seafood at James Pharmacy.

While there are plenty of great restaurants in Hillsborough, a meal at Saratoga Grill is a must. Open since 1995, the restaurant is a casual vibe but with an elevated menu best known for their seafood dishes.

And for an upscale date night in Hillsborough, Panciuto tops them all. Six-time James Beard-nominated chef, Aaron Vandemark doesn’t just throw out “local” as a buzz word. His menu comes from neighboring farms, friends, and artisans.

Across the street from all that is Radius Pizzeria. There, you can devour handmade pizza with ingredients sourced within 250 miles.

On the other side of the Riverwalk, you can grab a rack of ribs and all the fixings at Hillsborough BBQ Company. Outside of historic downtown Hillsborough, you can find perfectly crisp chicken and biscuits at family-owned Jay’s Chicken Shack.

And finally, no trip to Hillsborough would be complete without a stop at Matthew’s Chocolates. Choose from decadent and delicious rows of truffles and chocolate confections. You can enjoy a treat to take home or eat right away here!

Our Thoughts and Yours, Too

There have been very few places in North Carolina that hit us like Hillsborough did from the first time we visited. We fell in love with this small town and have kept coming back to create happy memories. If you live in Durham or Chapel Hill and haven’t spent much time here, please add Hillsborough to your list of places to go next.

If you have been to Hillsborough, we’d love to know all about your favorite things to do here. Let us know in the comments section or send us an email. And if you haven’t been lucky enough to visit this place, we want to know which of the things we mentioned that you’d like to do first.

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