HILLSBOROUGH, N.C., 2025 – After months of restoration following Tropical Depression Chantal, Hillsborough’s beloved trails and greenways are open once again, ready to welcome visitors. This small town along the Eno River is full of history, charm, and creativity, and its mix of shopping, dining, live music, and outdoor exploration makes for a small-town getaway with big charm.
Begin your adventure on the Riverwalk, a paved greenway that winds along the Eno and leads you straight into the heart of historic Hillsborough. From the trail, it is only steps to downtown’s boutiques, galleries, and restaurants, making it easy to pair outdoor activity with cultural exploration.
Shoppers will find plenty of treasures in locally owned stores. Carlisle & Linny Vintage Jewelry dazzles with one-of-a-kind pieces, while Uniquitiques offers antiques and quirky finds. Art enthusiasts can explore Spiral Studios or browse the shelves of Purple Crow Bookshop, a local favorite filled with must-reads. For fashion and home design, 108 Churton, Vesta, and Dwell Hillsborough showcase a chic mix of apparel and décor. Even plant lovers have their spot at The Flower Patch or Six of Cups, where greenery and gifts line the shelves.
When it is time to eat, Hillsborough delivers flavors as varied as the trails along the river. Savor barbecue at Hillsborough BBQ Company, grab a slice at Pizza Cornicione, or cool down with frozen custard at Whit’s. For an evening out, stop by Eno River Brewing for craft beer and a riverside seat, then head to Nash Street Tavern, where live music fills the air. Many nights in Hillsborough end with live music, whether it’s a bluegrass jam, jazz set, or local singer-songwriter performance.
A Town Steeped in History
Hillsborough wears its history proudly, and many sites are within a short walk or drive of downtown. The Occaneechi Replica Village, just off the Riverwalk, gives a fascinating glimpse into life along the Eno hundreds of years ago. For a mix of history and natural beauty, visit Ayr Mount, a Federal-era home built in 1815. Admission is charged for house tours, but the surrounding Poet’s Walk trail is free. This mile-long loop through meadows and shaded woods offers sweeping views of the Eno and stands as one of Hillsborough’s most peaceful spots.
Another can’t-miss stop is the Occoneechee Speedway Trail, the only surviving dirt track from NASCAR’s 1949 inaugural season. Today it is a preserved historic site, where visitors can walk the oval, explore the remains of the grandstand, and imagine the roar of engines that once echoed here.
Trails and Outdoor Adventures
While the town offers plenty to see, Hillsborough’s trails are the thread that ties it all together. The Riverwalk itself is ADA-accessible, family-friendly, and easy to reach from downtown parking. Along its path, you’ll pass River Park, a wide-open green space perfect for picnics, and Gold Park, a 20-acre favorite with trails, playgrounds, and an accessible musical play area for kids.
For those looking to stretch their legs farther, Hillsborough is a gateway to larger outdoor escapes. The Occoneechee Mountain State Natural Area offers a rewarding climb to the highest point in Orange County at 867 feet, with seasonal views that are breathtaking year-round. For a more relaxed outing, the Seven Mile Creek Natural Area provides wooded paths ideal for birdwatching and quiet reflection.
Festivals, Flavor, and a Weekend to Remember
Hillsborough is more than a day trip, it is a destination worth a weekend. Stay overnight at the beautifully restored Colonial Inn, where history meets modern comfort, or settle into one of the town’s cozy bed-and-breakfasts. Festivals and seasonal events fill the calendar, from the River Park Concert to the Outlandish Hillsborough Scottish Festival, along with art walks, music celebrations, and history-focused gatherings.
Despite the challenges brought by Tropical Depression Chantal, the town has rallied to restore its beloved outdoor spaces. Today, both the greenways and the businesses they connect are thriving again. Whether you come for boutique shopping, historic sites, a lively night of music, or a riverside walk, Hillsborough offers big adventures around every bend.
