Driving into Pinehurst and Southern Pines is like entering a well-manicured time capsule. Scrub pines and roadside gas stations give way to horse farms, pristine golf courses, century-old houses, and quaint villages perfect for meandering on a Saturday afternoon. Of course, Pinehurst’s crown jewel is its nine-course golf resort, with the famed No. 2 at its center. But whether it’s the golf that draws you to the area or simply the desire for a weekend’s change of pace, these two neighboring towns have plenty of charm, good food, and history to offer both on and off the resort.
1. Tee Time
Many visitors make the trip to “the cradle of American golf” to hit the links at one of the Pinehurst Resort’s nine world-class golf courses. Opened in 1907, No. 2 is the most celebrated of the bunch, having hosted multiple U.S. Opens, the PGA Tour Championship, and the Ryder Cup. No. 2 is notable not only for the legends who have played it, but also for its recent restoration to original landscaping, which features natural bunker edges and indigenous North Carolina grasses. Pinehurst has also done a lot to pioneer and support women’s golf, and unlike some of the country’s other top courses, all Pinehurst golf courses are open to the public. The clubhouse doubles as a museum, showcasing golf highlights from the resort’s founding to present day. A new bar overlooking the 18th hole of No. 2 opens this summer—a perfect spot to sip a mint julep with a slice of history in plain sight.
2. Village shopping
Wander through the winding streets of Pinehurst Village to browse its many boutiques and galleries. Visit Cool Sweats for printed muumuus and modern dresses, Le Feme Chateau for Italian masks and custom-made handbags, and the Roast Office, a beautiful coffee shop in an old post office that doubles as a used bookstore. In Southern Pines, browse staff favorites at the Country Bookshop, take a cooking class or sample olive oils at The Flavor Exchange, or pop into Denker’s, a clothing boutique with an original 1920s soda fountain.
3. Beaches and trees
Guests of the Pinehurst Resort can visit the picturesque Lake Pinehurst, where activities like sunbathing on the beach or renting kayaks and paddleboards offer a refreshing alternative to resort activities. If you’re not staying at the resort but still want to connect with nature, take a serene stroll through the Village Arboretum.
4. Southern comfort
After a day on the golf course, at the spa, or in town, nothing’s better than relaxing on a veranda and letting the sweet scents of honeysuckle and magnolia wash over you. Settle into one of the Carolina Hotel’s ubiquitous white rocking chairs and while away the afternoon. Opt for a seat outside the hotel’s west wing for views of the pool and expansive lawn, rather than the parking lot out front.
1. Walking tour of Pinehurst’s 120-year history
In 1895, soda fountain mogul James Walker Tufts purchased the 6,000 acres of sandy, barren land that would become Pinehurst and its surroundings. He hired prominent landscape architect Fredrick Law Olmstead (who also designed New York City’s Central Park) to create a resort village reminiscent of a New England town. Pick up a walking tour map at the Given Memorial Library and stroll through the charming village and lush, peaceful side streets lined with original cottages. If you’re not staying at the Carolina Hotel, make sure not to miss its wonderfully preserved grandeur.
2. North Carolina’s literary legends
Tucked away in Southern Pines stands the Weymouth Center for the Arts & Humanities, an elegant mansion that counted literary heavyweights Thomas Wolfe, F. Scott Fitzgerald, and Sherwood Anderson among its many guests. Considered to be the site that launched the Southern literary renaissance, the Weymouth Center now houses the North Carolina Literary Hall of Fame. The grounds are open daily, and tours of the Boyd House are available on weekdays.
3. A golf shop from another time
Among the many shops in Pinehurst Village stands The Old Golf Shop, which is as much of a golf museum as it is a store of memorabilia. Whether or not you’re a golf buff, it’s worth ducking into this one-of-a-kind store and chatting with owner Bob Hansen, who has been collecting golf memorabilia from around the world for 50 years and is one of the world’s foremost collectors. From 100-year-old feather golf balls, to antique clubs and tees, to the oldest golf scorecard in existence (circa 1820), there’s plenty to see here. You’re guaranteed to leave with a fascinating tidbit of knowledge, if not a collectible item.
Eat and Drink
1. Four-star classics and down-home fare
Inside the intimate Holly Inn, Pinehurst’s oldest hotel, you’ll find two excellent restaurants. Head below the stairs to the four-star 1895 Grille, which flaunts its history with a gorgeous vaulted beam ceiling. Find upscale, locally sourced takes on Southern classics, like the jumbo shrimp with artichokes and crème-fraîche-and-chive grits. For more casual fare, head to The Tavern, which boasts an antique Scottish bar and top-notch fried chicken.
2. Sandwich stop
Have lunch at Sweet Basil Café, a charming local gem on Southern Pines’ main drag. Sweet Basil is only open a few hours a day, but the wait to get in is worth it for the Hot Vegetarian sandwich (which, layered with avocados, pesto, and basil mayo, is much more than it sounds) or the Smoked Turkey Melt.
3. Local beer and lively music
The Drum & Quill is a Pinehurst institution, serving beer and food for nearly as long as the town’s been around. A classic, wooden interior strung with Christmas lights provides a cozy pub atmosphere, and live music on Friday and Saturday nights lends itself to impromptu two-stepping. The bar has local beer on tap and is also a popular lunch spot. Try the Duck Hook Cream Ale from Southern Pines Brewing and the Grand Pimento sandwich.
4. Farm, chef, table
Chef Mark Elliott bases his cooking philosophy on his “farm, chef, table” mantra. At Elliotts on Linden, ingredients come from local, North Carolina farms, creameries, vineyards, and dairies. The quality of the ingredients shows in the quality of the food, like the butternut squash tart or the rabbit and pistachio sausage.
5. Prime dining
Pair perfectly-cooked steaks with hand-selected wines at Southern Prime. At the bar, locals gather for expertly made cocktails, like an Old Fashioned with house-made spiced bitters or the Sweet Bourbon Cobbler. Ask for a table in the Wine Room, surrounded on all sides by a floor-to-ceiling wine cellar.
1. Carolina Hotel
The centerpiece of the Pinehurst Resort, the luxurious 280-room Carolina Hotel, evokes the era in which it was built, more than a century ago. Shuttles take guests to golf courses and the Village, and the resort’s spa is right next door. Sip mint juleps at the Ryder Cup Lounge and indulge in the overflowing breakfast buffet.
2. Magnolia Inn
The small Magnolia Inn is situated in a historic home right in the middle of the Pinehurst Village. Rooms are cozy and quaint, and the wraparound porches provide just the right amount of Southern charm. Golf packages are also available.