When I made my first trip to Pinehurst, N.C. for the 2014 U.S. Open, a whole new realm was opened to me in the world of golf. At the same time, I was kicking myself for not making it down sooner—I had lived just an hour away for most of my life.
Since 2014, I have more than made up for missed time in the Sandhills—almost to the point that Pinehurst became a second home. I spent the summer months back from college peddling Putterboy-logoed merchandise in the main golf shop, and since graduation I’ve jumped at every chance to sneak down to my slice of sandy heaven.
While Pinehurst Resort is undoubtedly the main draw to the area for many, it’s the abundance of great golf in the Sandhills that makes it especially alluring. Courses like Mid Pines and Tobacco Road are responsible for turning many “quick weekend trips” into extended long weekend stays, as they are not to be missed when in the area.
So, as a former local, here’s my perfect “all-in” long weekend in Pinehurst.
Arrival:
Fly into RDU International. If staying at the resort, a Pinehurst shuttle will pick you up from the airport and take you straight into Pinehurst. If there’s daylight left when you arrive, grab your putter and head out to the Thistle Dhu putting course with a beverage of choice.
Day 1:
Golf:
Round 1: Pinehurst No. 4
Gil Hanse’s phenomenal new No. 4 course features rugged waste areas, bold contours, and heavily undulated greens. It also sits on what is arguably the best piece of land on property which helps make the view from the new 6th green one of my favorites in the area.
Round 2: The Cradle
Keeping with the Gil Hanse theme, the Cradle is an endlessly entertaining short course that you can loop as many times as you want for $50. Be sure to stop at the Pinecone—a drink cart mid-round—for a beverage (one Transfusion, please).
Non-Golf:
Villager Deli
In between rounds, stroll into the Village for a sandwich at the aptly named Villager Deli. A staple for many locals, this was my go-to lunch spot during my time as an employee.
Pinecrest Inn
Participate in a Pinehurst tradition and try your hand at chipping into the famous fireplace at the Pinecrest. Linger and have a cocktail or two while you watch others attempt the fireplace shot.
Day 2:
Golf:
Round 1: Pinehurst No. 3
Often referred to as a “mini No. 2” due to its turtle-backed greens, Course No. 3 serves as a warm up of sorts for the real thing. Though for my money it stands alone as a fun, relatively short course that won’t beat you up.
Round 2: Mid Pines
Recently renovated back to its former sandy glory by Kyle Franz, Mid Pines is one of the most fun courses in the area. It’s always in great shape and routed magnificently with a strong finish—the stretch of 14-18 is one of my favorites in golf.
Non-Golf:
Pinehurst Brewery
Occupying the village’s old steam plant, this is one of the newest additions to the resort. The beer is fantastic, as is the barbeque. Come hungry.
Day 3:
Golf:
Round 1: Pinehurst No. 2
This is the reason why most people come to Pinehurst. It’s no secret that it’s tough, but go into the round with the right mindset and you’re in for one of the most magnificent experiences in the game. Be sure to take your picture with the Payne Stewart statue behind the 18th green.
Round 2: Cradle
Yes, again. After likely getting beaten up by No. 2, play the Cradle again to remind you that golf is supposed to be fun.
Non-Golf:
Pinehurst Track Restaurant
Known for their blueberry pancakes and actually located on the Pinehurst Harness Track, the tiny Pinehurst Track Restaurant has long been a favorite breakfast spot for locals. Fill up here before walking No. 2 but be sure to bring cash, as they don’t take credit card.
Dugan’s Pub
After a pint at The Deuce, head into the Village for dinner at Dugan’s. A favorite of Pinehurst employees, you might run into one or two having a beer or singing karaoke after their shifts.
Day 4:
Golf:
Tobacco Road
One of my favorite courses anywhere, Tobacco Road can also be heavily polarizing. With wild contours and an abundance of quirky shots, this Mike Strantz masterpiece is a must play as you’re driving back up to RDU airport.
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What is your perfect Pinehurst long weekend? Let us know in the comments section below!
