Things to Do in Pittsboro

By Vacationidea | Disclosure: I use affiliate links

Town of Pittsboro, NC

If you’re craving small-town charm with a creative twist, I’d love to point you toward Pittsboro. I found it tucked in the heart of North Carolina, and I think you'll really enjoy how it blends historic streets, vibrant art, and genuine Southern hospitality. When I explored the local galleries and wandered into a countryside winery, I felt completely at ease. You’ll get that perfect balance of nature, culture, and small-town peace here.

Best Time to Visit

I always plan my Pittsboro trips in the spring or fall—and I recommend you do the same. You’ll catch blooming dogwoods in March or colorful foliage in October, and I’ve stumbled into a couple of fun festivals just by wandering around. It’s not too hot, not too cold—just right for hiking or strolling downtown without breaking a sweat.

How to Get There

If you’re driving: I usually take US-64 or US-15/501, depending on where I'm coming from. It’s just 40 minutes from Raleigh and even closer to Chapel Hill. I’ve never had trouble navigating the scenic roads around here.
By Air: When I fly in, I land at Raleigh-Durham International (RDU)—about 45 minutes out. If you rent a car there, the drive feels quick and easy, especially if you time it outside rush hour.
By Bus: I wouldn’t count on a direct train, but if you’re coming from Chapel Hill or Durham, there are some regional buses. I’ve used them in a pinch and they’ve gotten me close enough.

Where to Stay

Rosemary House Bed & Breakfast – I’ve stayed here before, and if you like cozy vibes with a historic touch, this one's a gem. You’ll be just a short walk from everything downtown—and the breakfast? Absolutely worth waking up early for.
Fearrington House Inn – If you’re in the mood to splurge a little, I’d steer you here. I’ve spent a weekend surrounded by gardens, farm animals, and incredible food. You’ll feel pampered without it being stuffy.
Chapel Hill Hotels – Sometimes I stay in Chapel Hill for more options. It’s about a 25-minute drive, and you’ll find all the familiar names if you’re after something straightforward and convenient.