Located right off I-85 in Orange County, Hillsborough, one of the oldest towns in North Carolina, is the perfect spot for a little day trip getaway from eastern North Carolina. There are great local shops to browse and support, delicious restaurants, history to experience, and outdoor trails. Here is a round-up of what to do and where to stay in Hillsborough, NC! Hillsborough is a lovely, eclectic, quaint town with a whole lot of charm.
Hillsborough is so dang cute, y’all. Its historic downtown is fun for brunching, strolling the side streets, and browsing the local boutiques. Check out the Riverwalk in Hillsborough, which offers gorgeous views of the Eno River. After spending time downtown, head to Ayr Mount to explore the grounds and sit a spell on the property.
This article was originally written in March 2018 and has since been updated and recirculated for 2025.
Hillsborough Travel Guide: What to Do and Where to Stay
Hillsborough Travel Guide: Things to Do
Browse the Shops in Historic Downtown
One of my favorite ways to explore a town is to check out the local shops and the ones of downtown Hillsborough reflect the charm of the town perfectly! Carlisle & Linny Vintage Jewelry has the best vintage costume jewelry and 108 Churton boasts a great selection of home decor and clothing. A stop at Purple Crow Books is also a must! This bookstore specializes in local authors and offers signed copies of their works. Be sure to give the shop dogs a pet, too! For home decor, browse dwell for a thoughtfully curated selection.
Enjoy the Arts & Culture
Hillsborough is quite the haven for artists, featuring several art galleries. For 2021, they have the Last Friday Art Walk, which highlights local businesses. While there are limited capacities allowed in the venues, it is a great way to explore various types of artwork including fine art, folk art, and contemporary art. The Colonial Inn also has local artists’ work featured throughout their property.
Some venues feature live music, shows, and open mic nights, such as Volume Records & Beer, Yonder Southern Cocktails, and the Nash Street Tavern.
Learn More about the Area through the Historic Sites
The town was founded in 1754, and they have done a fantastic job of maintaining elements of the original architecture throughout town. Since my first few visits to town, there is now a mural to Billy Strayhorn, one of the most influential American jazz musicians. Strayhorn was a member of Duke Ellington’s band. His connection to Hillsborough was through his grandparents and his grandmother’s garden was one of his inspirations in his music.
The Burwell School Historic Site preserves and interprets the history of 19th century Hillsborough, including Elizabeth Hobbs Keckly, who was enslaved on the property. She later bought her freedom and was a dressmaker for Mary Todd Lincoln.
Other notable sites include the Historic Occoneechee Speedway Trail, Margaret Lane Cemetery, Occaneechi Village Replica Site, Orange County Historical Museum, and Ayr Mount. As these sites continue their work of interpreting and preserving history, I look forward to learning more about the people who made those properties possible.
Explore the Outdoors
Hillsborough is located right along the Eno River and close to Occoneechee Mountain State Park. While there are hiking, biking, and walking areas, the Riverwalk features about two miles of waterfront trails. You may also want to consider hiking Occoneechee Mountain, which is about 5 minutes outside of downtown. The Poet’s Walk is another great place to experience the Eno River.
If you are interested in picking your own flowers or your own strawberries, blackberries, and blueberries, check out the Eno River Farm.
Hillsborough Travel Guide: Where to Eat
Antonia’s
Antonia’s is an authentic Italian restaurant and uses locally sourced ingredients. I have heard nothing but great things about this restaurant and I am especially smitten with the fact that it has daily specials that are actually updated on their website and social media channels.
Antonia’s is at 101 N Churton St, Hillsborough, NC 27278.
Cup a Joe
This local hangout serves amazing coffee drinks, teas, and baked goods. I highly recommend the lavender honey latte and their pan au chocolate.
Cup-a-Joe is at 112 W King St, Hillsborough, NC 27278.
Hillsborough Bakeshop & Pasta Co.
Credit: Hillsborough Bakeshop Facebook
This restaurant serves up breakfast and lunch Wednesday-Saturday with a menu that changes frequently. It is also open for dinner on Fridays and Saturdays with the last seating at 7:30 featuring homemade pastas.
Hillsborough Bakeshop is at 110 S Churton St, Hillsborough, NC 27278.
The Nomad at the Osbunn
Nomad is an incredible concept in the Osbunn building, the former town theatre. This unique restaurant features a truly one-of-a-kind dining experience. Nomad takes you on a culinary journey like no other, offering a diverse range of traditional ethnic dishes and expertly crafted cocktails, each with its own unique twist. Make a reservation!
The Nomad at the Osbunn is at 122 W King St, Hillsborough, NC 27278.
Spencer’s Tavern at the Colonial Inn
The tavern is located in The Colonial Inn and is a gorgeous, quaint spot with an excellent selection of drinks and a delicious food menu. It is beautifully restored and a cozy, inviting spot. The kitchen offers daily specials and their pimento cheese comes highly recommended! Do try their burger with their homemade bacon jam.
The Colonial Inn also serves Sunday brunch, which was a longstanding tradition at the Colonial Inn. You will need to make reservations in advance and I’ve heard the fried chicken is a must.
Spencer’s Tavern is in The Colonial Inn at 153 W King St, Hillsborough, NC 27278.
The Wooden Nickel Pub
The Wooden Nickel has been the neighborhood pub of Hillsborough since 2003, featuring some of the best wings and loaded cheese tots! The menu changes frequently and the pub has the finest craft and draft beer selection available. There is also a great outdoor seated area perfect for people watching.
The Wooden Nickel is at 113 N Churton St, Hillsborough, NC 27278.
Hillsborough Travel Guide: Where to Stay
The Colonial Inn
The Colonial Inn was such a great location in downtown historic Hillsborough. It is within walking distance of the best restaurants and shops in downtown. This recently renovated gem in Hillsborough opened its doors in November 2020. It’s a perfect mix of original pieces and modern touches.
There is a great attention to detail with the staff at the Inn. Before checking in, we received communication from the hotel to see what our preferred room temperature is so it would be set at that, plus our mattress preference, and if we wanted extra pillows and blankets. It was quite lovely to have that level of attention even before arriving. Enjoy breakfast service where premium coffee, homemade cinnamon rolls and coffee cake are available in the commons area.
The Colonial Inn at 153 W King St, Hillsborough, NC 27278.
Photos by Glory Roze Photography
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I lived in Hillsborough for four years and think you have done a great job recapping what there is to do.
Thanks so much, Lee!
Next time, you should head over to Nash Street at the other end of the Eno River walkway. Mystery Brewing and Hillsborough BBQ are amazing, and there’s a great view from the Mount Occoneechee Natural Area that you can drive to or walk to from a path by the bridge.
Thanks so much for those recommendations! I’ll definitely check those out on our next trip.