A First Timers’ Guide to Pinehurst & Southern Pines | Our State (2024)

“Am I doing this right?” I asked my husband, Alex. I squared up to the golf ball at Hole 1, my putter held just so, gently adjusting my feet until they felt just right on the turf as I mimicked the golfers I’d seen on TV. He nodded seriously. Around us, Pinehurst Resort was buzzing. A gentle breeze was stirring, the sun was shining, and my icy-cold drink was sweating in its drink stand next to me. In the distance, I could hear roars from the crowd.

“There you go,” Alex said. “Now, just barely tap it.” I gently swung the putter like he’d shown me, hardly raising it off the ground. My ball got air and shot across the green like it was a rocket ship past several groups and maybe even through a pair of legs, rolling to a stop around Hole 5. Did I mention that this was not the iconic Pinehurst No. 2 but Thistle Dhu, Pinehurst’s 18-hole putting course? And that the roars from the crowd were from good-natured hecklers on the nearby par-3 course, The Cradle?

“I guess I don’t know my own strength,” I mumbled to nobody, since Alex was laughing so hard that he was choking on a sip of his beer and had to set it down. “That — that was —” Alex saw my face and straightened up to retrieve my ball, tugging the corners of his mouth down. “Well, let’s just try that again,” he said.

Luckily (for me), as we played through the rolling course, Alex — who fancies himself a golfer — had a much tougher time than he expected. At several holes, my shot was better than his. “This is very tricky,” he said more to himself than me. “Much trickier than I was expecting.” I stifled my own grin and took a sip of my drink. “It sure is fun trying, though,” I said, as he scoffed.

I knew then that the weekend ahead would be full of surprises in the best way. It was our very first trip to the Home of American Golf, which was a dream come true for Alex, but there were plenty of other items on our to-do list that we were excited for — from delicious restaurants to outdoor adventures — and I have to say we hit a hole in one with our itinerary. (Metaphorically, of course … As you can probably tell by this point, we’re pretty bad at golf.)

Here’s how to spend your own delightful spring weekend in Southern Pines, Pinehurst, and Aberdeen — no golf skills required.

Day 1:

Check into The Jefferson Inn: Half a block from the train station in historic downtown Southern Pines, this 14-room boutique hotel welcomes guests with a long front porch filled with white rocking chairs and hanging ferns. The former residence dates to the late 1800s, when a couple from New Hampshire built it as their winter getaway. Eventually, they attached a nearby dry goods store and started taking in guests. Today, newly renovated rooms offer guests modern-day luxuries in the heart of Southern Pines, including a cozy lobby “living room” with oversized leather chairs, suites with fluffy beds, and expansive bathrooms with claw-foot tubs. Resist the urge to immediately face-plant into the dreamy duvet, like Alex did.

Pop over to Pinehurst to explore the village: I know, I know — you just got here. But don’t worry, it’s just a 10-minute drive to Pinehurst from the Jefferson, and you’ll spend the whole day in Southern Pines tomorrow. In Pinehurst, park the car near Market Square and just start wandering. My biggest surprise as a first-time visitor: Just how charming and quaint it all was. The shops, the restaurants, the inns, and even the quiet, leafy side streets looked straight off a movie set. I think I told Alex that about six times, but to his credit, he agreed with me six times, and even got specific: “Straight out of a Hallmark movie.” (Proud wife moment for that reference.) Some favorite stops: Alex could have spent all afternoon browsing Old Sport & Gallery, which is part art gallery, part bookshop, and part antiques and memorabilia shop. Be sure to take a minute (or 20!) to chat with the fascinating and friendly owner, Tom Stewart. I loved Purple Thistle Kitchen & Co., which had lots of great gifts for foodies. We both loved the Village Wine Shop, which has bottles, of course, plus wine by the glass, beer, coffee, and a shady sidewalk patio.

Take a walking tour through village history: One of my very favorite things we did was simply stroll along the curving streets of the New England-style village — designed by Fredrick Law Olmsted, the designer of Central Park and the ground of Biltmore Estate — admiring all the historic homes and their beautiful gardens, many of which were built more than a century ago. The entire village — which sprang up around historic Pinehurst Resort, established in 1895 by James Walker Tufts — is designated a National Historic Landmark. Next time we visit, we’ll pick up a copy of the Village of Pinehurst: A Historic Walking Tour from the Tufts Archives and explore some of the carefully planned walking tours for a deep-dive.

Play a round — or sip a co*cktail and sit in an Adirondack: After exploring the village, we headed over to the grounds outside of the impressive, red-roofed Pinehurst Resort Clubhouse to play the Thistle Dhu putting course. Unlike Donald Ross’s Sandhills masterpiece, the world-renowned No. 2, which rambles just past the other side of the clubhouse, this family-friendly 18-hole putting green is free to play — all you need in a ball and a putter. Fun fact: When it was built in 1916, it became the first miniature-golf course in America. Also adjacent is The Cradle, a nine-hole, par-3 course. The best part (for me): Positioned on a small hill between the two courses sits the Cradle Crossing, an open-air bar where guests can grab a cold drink — try the Transfusion, a Pinehurst classic — and sit a spell in an Adirondack chair to watch the fun and revel in the atmosphere. Or take your drink with you — both The Cradle and Thistle Dhu have handy little drink stands at each hole. Oh, and don’t be surprised by bare feet: As we stood in line at the bar, I looked around in confusion at all the grown men and women who were walking around completely shoeless. Alex leaned in to ask the bartender why, and she informed us that bare feet were suggested at The Cradle — to keep the play informal and to protect the turf. Suffice it to say, it’s still a funny sight.

Eat dinner at Elliotts on Linden: After a day in the sun, sip a co*cktail and indulge in local farm-to-table fare on the beautiful patio of this elegant dinner spot. Alex and I split the North Carolina shrimp with ale and cheddar stoneground grits to start, which was amazing, and then I savored the lemony, garlicky, truffle-dusted scallops and a side of truffle macaroni and Gruyere cheese while Alex indulged in a spicy cheeseburger special that was cooked to perfection. And crunchy-fry lovers rejoice: The triple-cooked fries with garlic aioli are a delight.

Enjoy after-dinner drinks and live music at Drum & Quill: After dinner, we ventured back over to the village for a little entertainment. There are plenty of good spots for drinks, but we liked the sidewalk patio at Drum & Quill Public House. (If you like your music louder, sink into one of the cozy red-leather booths inside.) Arnold Palmer was still in high school when owner Kevin Drum’s dad, newspaperman Bob Drum, discovered the soon-to-be-legendary golfer and began penning his praises. When it came time for Kevin to name his Pinehurst pub, he combined his dad’s last name with a writerly symbol. We stuck with drinks, but the food looked incredible, too. I might just have to return for the fried tomato sandwich with melty pimento cheese. We also struck up a conversation with several locals who darn-near convinced us to move — or at least visit for what sounds like an amazing Halloween.

Day 2:

Eat breakfast at Betsy’s Crepes: Just a couple blocks from The Jefferson Inn, you’ll find one of Southern Pine’s favorite breakfast joints, which has perfected the ultra-thin-pancake-like French pastry. To avoid a wait, go early. The menu includes dozens of sweet and savory crepes, from classic to creative, plus breakfast sandwiches, waffles, and more. I was paralyzed by my typical breakfast conundrum — sweet or savory?! — so I ordered the huevos rancheros crepe, and Alex and I split a “Sweet & Simple,” a sweet, buttery crepe dusted with powdered and cinnamon sugars. Everything was incredible.

Find the oldest pine in Weymouth Woods: Just a few minutes’ drive from downtown Southern Pines, you’ll find the Weymouth Center for the Arts & Humanities. Park here to explore the stunning public grounds and gardens surrounding the Boyd House, a historic Georgian mansion on the property and the former home of American poet and novelist James Boyd. But also plan to venture further on the property to explore the Boyd Tract, part of the 930-acre Weymouth Woods Sandhills Nature Preserve. The Boyd Tract contains about 100 acres of old-growth forest, and layers of pine needles make the whole adventure feel hushed. Follow the sandy Round Timber Trail, a gentle 1.5-mile loop that will take you past the oldest-known longleaf pine in the world. (Alex may or may not have picked up the biggest pinecone either of us had ever seen and taken it home with us.) You might also spot equine friends — many trails in Weymouth are horseback-rider-friendly.

Fuel up at The Bell Tree Tavern: After walking off your crepes and working up an appetite, head back to downtown Southern Pines for lunch on the expansive back patio at this old-school pub. Alex and I were feeling snacky, so we ordered fried pickles, chicken tenders, and Mozzarella sticks to share — and they were all incredible, especially when dipped into the house-made ranch. But the burgers looked amazing, too.

Stroll, shop, and sip in downtown Southern Pines: In the afternoon, pop into local shops like R. Riveter for handmade leather bags, Mockingbird on Broad for home goods and gifts, The Heritage Flag Company for incredible wood American flags made from reclaimed whiskey and wine barrels, and The Country Bookshop for a new read; the bookstore has been a staple in town since it opened in 1953. For an afternoon brewery tour, check out Hatchet Brewing Company, then head two blocks down to Southern Pines Growler, before finally ending up at Southern Pines Brewing Company on Pennsylvania, just two blocks further, where you can sip your local brew — Alex loved the Duck Huck blonde ale — on the breezy outdoor patio beneath a towering magnolia tree. Just be sure to ask for a “passport” at your first brewery; all three spots are stops on the Sandhills Pour Tour, during which a seven-stop passport guides you to Moore County’s beer and cider spots — and a fully-stamped passport wins fun prizes.

Eat dinner at Chef Warren’s Bistro: Specials and seasonal entrées prepared with French techniques are delicious, but the staples — steak and fries, lobster Rangoon, and pecan pie — have attracted diners since this local restaurant opened in 1998. That pie? It comes warm, with homemade vanilla ice cream and caramel sauce, and it really is worth a visit in and of itself.

Savor an after-dinner delight on the front porch of The Jefferson Inn: If the pecan pie isn’t enough, stroll over to The Ice Cream Parlor Restaurant — on the same block as the Jefferson — for an old-fashioned ice cream sundae. Then take it back to the front porch to enjoy it in a rocking chair as the sun sets.

Day 3:

Start your day at Mason’s Restaurant & Grocery in Aberdeen: After sleeping in and checking out at 11 a.m., make the 10-minute drive over to Aberdeen for brunch at this local favorite. I resisted round two of huevos rancheros in order to try the Birdies Hot Mess, a three-egg scramble with onions, bell peppers, smoked ham, potatoes, and cheddar and sausage gravy. Yes, please. Oh, and plenty of coffee, of course.

End your journey in Seagrove: Before you leave the Sandhills, head to Seagrove. The town is located in the geographic center of the state, but for many people, it’s the center of the pottery universe. It may be small, but it boasts the largest concentration of working potters in the United States. Here, artists like Sid Luck — a fifth-generation potter — built a community of studios and shops from the ground up. Take a self-guided tour of artists’ studios; there are more than 50 galleries and pottery shops to explore. (Tip: If it’s Sunday, aim to arrive after 1 p.m., since many shops open late.) As we drove the beautiful winding backroads of Moore County, our newfound love of the Sandhills was cemented — and the makings of a return trip began to take shape. Maybe I’ll even work on my swing.