Pittsboro: Southern Charm with a Twist

Enjoy scenic views along with shopping, gardens, restaurants and spas at Fearrington Village, just northeast of Pittsboro.

Pittsboro, the Chatham County seat due west of Raleigh, is an eclectic mix of quaint, old-fashioned stores and boutiques along with new businesses including yoga studios, outsider art and hidden gems.

Chatham County Courthouse

Downtown Pittsboro has plenty of charm starting with the Chatham County Courthouse and Historical Museum, open for guided and self-guided tours. On a stroll through the downtown, you’ll pass several eateries, apparel shops and Pittsboro Toys, a locally owned toy and book store offering unique gifts and classic toys.

The former textile town also boasts a funky side with Circle City Books & Music, a locally owned bookstore with a nice selection of used books, CDs and records. Or hang out at the Joyful Jewel, which sells art and crafts, as well as painting and other art classes.

Be sure to check out the eclectic French Connection, a globally sourced gift shop. The rooms are filled with one-of-a-kind crafts, baskets, jewelry and fabric from France and about 20 African countries.

Angelina’s Kitchen

Have a seat at the table

Pittsboro is full of farm-to-table restaurants. Angelina Koulizakis, owner of Angelina’s Kitchen, is credited with being the pioneer of the “farm-to-fork” concept in Chatham County. She prepares locally sourced food with a Greek twist, including Avgolemeno (Greek lemon chicken soup).

Savor the flavor at The Natural Chef Café, which serves international-inspired meals prepared by students enrolled in the Central Carolina Community College’s Culinary Arts Continuing Education program (cash only). Some of the most recent lunch menus were Portuguese, Irish and Peruvian inspired.

Or try sandwiches and Southern classics from the Root Cellar Pittsboro or Carolina Brewery & Grill. Enjoy lunch or a treat from the Phoenix Bakery.

Craft beverages and sleepovers

Pittsboro offers plenty of tours and tastings between Starrlight Mead, the honey winery; Fair Game Beverage Company, known for its bestselling Tobago Pepper Infused Vodka (the perfect ingredient for a Bloody Mary); and Chatham Cider Works, which makes small batches of hard cider from NC apples and pears.

Then prepare to stay overnight at one of the three bed and breakfast inns in town. Make yourself at home at the Rosemary House, located downtown. The traditional home features fun folk art and offers a hot breakfast in the morning.

French Connection

Also check out the Small Street B&B Café. The breakfast and lunch venue also houses three creative guest rooms and the Small Museum of Folk Art, a changing collection of more than 400 pieces of art.

Or rest and relax at the classic 458 West Bed and Breakfast. Enjoy a hearty Southern breakfast and watch the world go by on the large wraparound porch.

Fearrington Village

Spend a whole day northeast of town at the upscale retirement community Fearrington Village. Wander its boutiques and gardens, splurge on meals, or indulge in spa treatments. McIntyre Books hosts both local and national bestselling authors for readings.

Seasonal fare is offered at both the casual dining Belted Goat and the fine dining Fearrington House Restaurant. Or you can just sit and enjoy the whimsical gardens filled with flowers and whirligigs.

This resident tiger is one of ten species you can see at Carolina Tiger Rescue.

Small Town, Big Cats

Carolina Tiger Rescue, an organization dedicated to protecting wild cats, is less than 10 minutes from downtown. Consider making a reservation to admire more than 10 species, many rescued from dire straits. Learn more at carolinatigerrescue.org.