Buddy Golf Trip

You’ve been friends since college. They stood up for you at your wedding.

You’ve been there for each other through all of life’s ups and downs. The stories you can tell about each other would fill a book. How long has it been since you’ve all gotten together for a break from your relentless schedules and responsibilities? Too long. Round up the guys and let us help you write the next chapter.

Day 1

Arrive, check in, and ease into Sandhills mode. If you’re itching to swing a club but don’t want a full round after travel, head straight to The Cradle — Pinehurst Resort’s wildly fun nine-hole short course that feels like a golf party disguised as a warm-up. Pair it with a drink, a little chirping, and just enough competition to set the tone for the trip.

Right next door, keep the laughs going at Thistle Dhu, the massive putting green inspired by the old-school “Himalayas” concept. It’s the perfect way to shake off the drive, settle a few quick bets, and get the group talking trash in the best possible way.

If the weather doesn’t cooperate, pivot to golf history instead. The USGA Experience and World Golf Hall of Fame at Golf House Pinehurst is an easy win — interactive, walkable, and packed with memorabilia. If your timing lines up, make a point to see “Style and Substance: The Life and Legacy of Payne Stewart” — a moving and unforgettable display tied to one of the most iconic finishes in U.S. Open history.

When it’s time to eat, grab a first-night pint at Pinehurst Brewing Company in the restored steam plant. Keep dinner simple and classic at Dugan’s Pub in the Village — hearty sandwiches, fish and chips, and the kind of place where a buddies’ trip feels instantly official.

Day 2

Settle in and get ready for world-class golf. If Pinehurst No. 2 is on your bucket list, you’ll be playing in the footsteps of grand champions. No matter how you play, you’re bound to walk off feeling like a legend.

Before you head out, blend in with the effortlessly stylish locals at Gentlemen’s Corner in the Village of Pinehurst. The fashion-forward staff will gladly get you dialed in — well-tailored, graceful, with just enough color to brighten your day.

After your round, lean into Pinehurst’s new era of golf history at the USGA Experience and World Golf Hall of Fame. If you didn’t catch it on Day 1, this is the perfect time to see the Payne Stewart exhibit.

Now it’s time to toast the day. Stop by the Pinehurst Brewing Company for a pint, then head to Pine Crest Inn for hearty, can’t-miss comfort food. Retire to the cozy on-site pub after dinner for a few well-earned pints by the fireplace — and raise a glass to good times with good friends.

Day 3

If you wake up early enough to get in two rounds, head to Southern Pines, home of Talamore Golf Resort, where you can build a full day around championship golf. Tee it up at Talamore or Mid South, then add a fresh twist by working in Legacy Golf Links in Aberdeen — now part of the Talamore family and playing a renewed role in the Sandhills golf lineup after major upgrades and renovations.

If you don’t grab a bite at the course, hit charming Chapman’s Food & Spirits for a hearty lunch with unexpected touches like bacon jam and “Lobsta Fries.”

For a quick, only-here golf detour, swing through Pinehurst for the Golf Pride Retail Lab — a surprisingly fun stop where the world’s leading grip brand showcases the only physical connection you have to the club. Or, if your group loves friendly competition without the scorecard stress, head to Wee Pines at Olmsted Village, where two newer mini-golf courses keep it light and memorable.

Round out the afternoon with local craft beer. Visit Southern Pines Growler Company for an impressive collection of beers from local brewers, across the country, and around the world. That evening, Red’s Corner is a popular outdoors gathering spot for locals and visitors alike with its Food Truck Park and 12-tap beer garden.

Day 4

You’ll want to make time for one more unforgettable round once you catch a glimpse of the picturesque Tobacco Road. It’s bold, scenic, and guaranteed to give you something to talk about on the ride home.

Another great option for Day 4 is circling back to Legacy Golf Links if you didn’t play it on Day 3 — or using it as the perfect “departure-day” course, close enough to keep the schedule sane while still delivering a full Sandhills experience.

Swing by veteran-owned Railhouse Brewery for one of their signature (and slightly irreverent) brews. A stop at the locally renowned Robert’s Golf Shop will let you stock up on clubs, accessories, and any last-minute trip essentials.

Wrap up with dinner at Southern Prime for a mouth-watering steak, Beefeaters for a feast from their meat- and seafood-heavy menu, or Dugan’s Pub in the Village for a hearty sandwich or their famous fish and chips.

Ready to book your trip? Check out our golf packages page!