With a downtown historic district listed on the National Register of Historic Places and more than 100 buildings that date back to the 18th and 19th centuries, Hillsborough has rightly been called a museum without walls.
Hillsborough is among the oldest communities in North Carolina — it was founded in 1754 — and the small town retains much of its historic charm, but shops, restaurants, attractions, and lots of green space give it plenty of modern appeal.
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Wander by the river
The idea to develop a trail hugging the banks of the Eno River was introduced in 2001, but it took more than a decade of planning and construction to bring that vision to life. The Eno Riverwalk was worth the wait. The 1.8-mile paved trail runs alongside the Eno River from Gold Park through downtown Hillsborough, and is part of the statewide Mountains-to-Sea Trail (and one of the few sections of the trail that pass through an urban environment). The Riverwalk is a popular spot for walking, running, and biking, and, thanks to the path it carves through downtown, it’s a great place to get a quick dose of nature.
Tip: The easiest points to access the Eno Riverwalk are the Eno River parking deck downtown (228 Churton Street) and Gold Park (415 Dimmocks Mill Road).
Grab a drink and some grub
The menu at the Wooden Nickel Pub features traditional pub fare along with a few creative takes on the classics: The bahn mi burger, made with pickled Asian vegetables, cilantro, umami mayo, and sriracha, is one of nine burgers on the menu and will become an instant favorite. The pub also stocks several North Carolina craft beers, and servers are pros at pairing brews and burgers.
Tip: The chicken wings are a crowd favorite. Choose from 10 different sauces like sweet Thai chili, Fricken’ Nickel hot sauce, and the Brewery of the Month sauce, made from local craft beer.
Wooden Nickel Pub
Appreciate the arts
Art lovers should be sure to stop at Eno Gallery and Hillsborough Gallery of Arts. The galleries, which are both located in the downtown historic district, carry contemporary fine art and feature the work of local artists. Admire glassworks, ceramics, sculptures, and wood pieces, along with watercolor and encaustic paintings. Featured exhibitions rotate monthly.
Tip: The artist-owned and -operated Hillsborough Gallery of Arts unveils its new featured show on the last Friday of every month.
100 South Churton Street
Hillsborough Gallery of Arts
Race through history (by foot)
The original Occoneechee Speedway Trail through what is now the James M. Johnston Nature Preserve was meant for driving, not walking: In the 1940s, NASCAR expanded an old horse racing track into a one-mile dirt track. During its inaugural race season, the oval track, known as the Occoneechee/Orange Speedway, was the place to be on a Sunday afternoon. Countless cars sped around the track between 1948 and 1968. Today, the 44-acre site is on the National Register of Historic Places ,and walkers have replaced race cars on a four-mile trail that follows the old NASCAR track and runs along the banks of the Eno River.
Tip: The original grandstands remain on-site; sit a spell and imagine 15,000 screaming fans cheering on their favorite driver — or just listen to the sounds of nature.
James M. Johnson Nature Preserve
Open a new chapter
Hillsborough has been called “one of the most literary communities in the state,” and nowhere is the passion for reading more evident than at Purple Crow Books. Sharon Wheeler opened the bookstore in 2009 and has hosted notable national and regional authors, including Hillsborough resident Frances Mayes, author of the best-selling book Under the Tuscan Sun. The small shop is chock full of great reads.
Tip: The bookstore specializes in local authors. Check out the local authors section for copies of signed books from notables like Jill McCorkle, David Payne, and Annie Dillard.
Purple Crow Books
Take a hike
Occoneechee Mountain is the highest point in Orange County, and the Occoneechee Mountain Loop Trail is the path to the summit. The two-mile trail traverses some steep terrain, but the views from the top are worth the climb. Looking for more of a stroll? The Brown Elfin Knob Trail follows a short path and passes through stunning rhododendron and mountain laurel thickets that provide riotous spring color. Elsewhere in the 190-acre state park, there are ponds for fishing and wading and large open areas for picnicking. Stop at the park office for plant and animal checklists to see how many species you can identify during your visit.
Tip: Rangers lead regular interpretive programs such as pollinator walks and “canoeing with a ranger” excursions. Check the website for upcoming events.
Occoneechee Mountain State Natural Area
Step back in time
Constructed in 1815 and listed on the National Register of Historic Places, Ayr Mount was the first major brick home to be built in the area and remains one of the best examples of Federal-era residential construction in the region. Merchant William Kirkland named the plantation house for his birthplace of Ayr, Scotland, and several of his personal artifacts are on display in the home. And while the home might be the crown jewel, the grounds are worth a visit, too. Stroll along Poet’s Walk, a one-mile trail on the grounds of Ayr Mount Historic Site, and explore an old Indian trading path and the Kirkland family cemetery.
Tip: Guided tours ($12 per person) are available between March 15 and December 15. Interpreters offer interesting insights into the history and significance of the plantation home.
Eat elevated farm-to-table fare
At Panciuto, “an Italian restaurant working with Southern ingredients,” chef and owner Aaron Vandemark, a six-time James Beard Foundation semifinalist for Best Chef in the Southeast, serves delicious farm-to-table fare. Try creative dishes like bucatini served with grilled dogfish, a tomato-cotenne-breadcrumb sauce, arugula, and anchovies; and sorghum-glazed pork shank served with a polenta pancake, scallions, and spinach.
Tip: Panciuto is open for dinner Wednesday through Saturday. Make reservations to guarantee a table at this local hotspot.
Stop and smell the roses
The gardens on the 61-acre private estate of Montrose date back to 1842. After purchasing the estate in 1977, Nancy and Craufurd Goodwin became the caretakers of the historic Montrose Garden, tending to tens of thousands of trees, shrubs, and flowers in all the colors of the rainbow. The grounds feature rock gardens, alpine gardens, woodland plantings, and vast expanses of sun-loving annuals and perennials. A local artist designed and built all of the fences, trellises, and arbors that add architectural interest to the gardens.
Tip: Tours of the garden are offered at 10 a.m. on Tuesdays, Thursdays, and Saturdays from May through September by appointment. No reservations are needed to attend the annual Garden Open Day in the fall.
Speak to the spirits
Hillsborough is haunted, and local ghost Enoch Pugh (who died at the gallows in 1771) wants to share stories of the spirits and hauntings around town. The Original Ghost Tour includes more than a dozen stops around downtown. At each one, a costumed guide shares real (and well-researched) stories about the dark side of Hillsborough, including local lore and the executions and mysteries surrounding various historic sites. The tour starts at 7 p.m. and lasts two-and-a-half hours.
Tip: Shorter tours, including a one-mile “Haints Misbehaving” ghost tour, and daytime historic tours (no ghosts) are also offered and earn rave reviews for their creativity and historical accuracy.
Haunted Hillsborough Ghost Walks