A definitive buddies’ guide to life (and death) at Pinehurst

What happens when six college pals go on the golf trip of a lifetime?

PINEHURST, N.C. — It’s not far from golf heaven to real heaven. On a good day at Pinehurst, the promised land is roughly the distance of a hard swing at a 56-degree wedge.

I know this reality because I have come into concerningly close proximity with it. For those of us hoping to avoid an untimely meeting with our creator? Keep a watchful eye around the tiny swathe of golf heaven fittingly called “The Cradle.”

Our would-be assailant wore a matching, head-to-toe ensemble that’d make Rickie Fowler blush. His one-piece, buttoned-down number featured powder blue flowers, a matching bucket hat and (most noticeably) the outward appearance of children’s pajamas.

If not for a sharp eye and well-timed yell from my playing partner Connor, I might not have seen our strangely dressed friend’s ball as it rocketed in my direction. A keen sidestep allowed me to dodge the shot comfortably. Drew and Chris, two of the other members of our sixsome at Pinehurst Resort, weren’t as lucky. Connor’s scream sent them straight to the deck, their fresh cocktails flying.


The golf ball smashed into an oversized drinking cart made from old oak called “The Pinecone.” The cart proved an ample backboard for the bladed chip, sending the ball rolling back to the cusp of the green.

Down at the tee box, the man looked apoplectic. Half the course had witnessed him nearly kill us. His friends on the tee box howled. If only he knew the fate that loomed six holes away…

The Pinecone, seconds before a brush with fate.

I. Here we go.

OUR JOURNEY to golf heaven began in early January, when I penned a short blurb for GOLF about a trip I hoped to take in 2021:

“Back when we were students at a certain frigid ACC school, my buddies and I established an affinity for road-tripping to the greener (read: warmer) pastures of North Carolina. The state (and its cities) are beautiful, cheap, and fun, particularly for a group of young bachelors. This year, we’re running it back and heading to the home of (American) golf, Pinehurst, for the buddies’ weekend of a lifetime.”

A few days later, I received an email from Pinehurst.

“Let’s make it happen.”

After a few weeks of back-and-forth, our trip was set. We’d see two cities, drive three cars, sample southern delicacies, drop in with friends from college and the professional world, and play six world-renowned golf courses: Tobacco Road, the Cradle and Pinehurst Nos. 2, 3, 4 and 8. We’d also pilfer through the area’s famed beer culture, devour bottles of wine and inhale a bottom-of-the-bar tequila shot (or 3 … or 7).

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There were six of us on the trip: Chris, Tyler, Drew, Tim, Connor (“Fred”) and myself. Once upon a time, the six of us spent most waking moments together as students at Syracuse University. But we hadn’t been together since the night before graduation more than two years prior.

 On the morning of our flight to Raleigh, Connor wore an awestruck smile. “I can’t believe this is actually happening,” he said.

Neither could I.

II. The Trophy

WE PLAYED for bragging rights, mostly. But there was also something bigger on the line: the first-ever Beta Sig Cup.

Weeks before we left on the trip, Connor and I hashed out our competition. As a sixsome of widely varying skill levels, finding a format to equitably divide the competition was … challenging. We settled upon a convoluted scheme involving points, handicap indices, and a varying series of games.  The goal was to make each event worth its overall value to the trip — a casual afternoon nine at The Cradle would take on less value than No. 3, which would also take on less value than No. 2.

But any washed-up frat star can create a golf tournament for his buddies. It takes a special kind of idiot to purchase a legitimate trophy for the purposes of crowning a champion.

Fortunately, I’m a sucker, and the internet market for golf trophies is well-stocked. After several hours, I settled upon a cast-iron beer stein, staving off the urge to purchase some of the more “interesting” hardware options, which ranged from delightfully phallic (who knew they made that in chrome?) to outright ridiculous ($700 for a sterling silver cup? Don’t mind if I don’t!).

A closer look at the hardware.

Our trophy was small enough to fit in my carry-on, sturdy enough to stay intact for years and, most importantly, capable of handling roughly 12 liquid ounces. I couldn’t wipe the smile off my face when I surprised our group with the trophy on our first night. We took turns sipping from it, passing it around to each member. Before long, the trash-talking began.

Only one of us would be capable of taking home “the cup” from our week at Pinehurst. Now it was time to figure out who.

III. Reunion!

WE WERE an unusual group to be attending a golf trip together, largely because we’d spent the formative years of our friendship in one of the most golf-barren areas on earth.

Syracuse, N.Y. is 35 miles as the crow flies from the nearest professional-caliber course, but it might as well be 35,000. Syracuse’s golf season is five months long ­— from May through September — and shorter in years when winter stretches long. The remaining months are filled mostly by snow. Every year, Syracusians take pride in competing for the only documented form of seasonal depression iconography: a trophy called “The Golden Snowball” given annually to the town in Upstate New York with the most inches of snowfall in a single calendar year. (Syracuse has won seven times since 2010.)

For six young men enrolled at Syracuse University with summer plans of internships and time at home, golf fell low on the list of priorities — somewhere between “class” and “sleep.” Instead, we became friends the way most Syracuse students become friends: a not-insignificant allotment of Labatt Blue Light.

The Canadian light beer proved the perfect social lubricant for our group, and soon became the launching-off point for our counter-cultural rebellions. Our chief enemies were fraternities, who we protested by anointing our friend group “Beta Sigma Sigma Gamma” (Greek for B-E-E-R — Socrates would be proud). We sold shirts with our lettering on campus, reveling in sideways looks from real frat bros and giggles from freshmen. Later, we had the letters etched into our golf trophy.

The glory days with Beta Sigma Sigma Gamma.

On the three (or fewer) days each year when we weren’t at our beloved campus radio station, at home, or buried under several feet of snow, “Beta Sig” would sneak out to Syracuse’s campus course, a delightful dog-track named Drumlins Country Club.

Through a deal with the University, students could play for free on the West Course, the property’s public offering. Truthfully, that was an upsell. Drumlins West existed in a perpetual state of disarray, with dirt tee boxes and design features that one could charitably describe as “nonsensical.” For example, the 18th, a par-3 where players hit tee shots from range mats over the side of a ravine, then scaled down it to the green below.

I’d like to think Mike Strantz would have enjoyed Drumlins West, or at the very least, would have gotten a kick out of our friend group drawing comparisons to our beloved college course as we stood on the 1st tee of his magnum opus, Tobacco Road.

Whereas Drumlins West is a likely product of architectural laziness, Strantz’s design at Tobacco is deliberately unhinged — its 1st hole is a 558-yard par-5 that bisects a rock quarry into a blind green. And that’s only the beginning of the absurdity. The course is 18 consecutive holes of sensory overload, overflowing with forced carries, blind tee shots and a borderline-unhealthy dose of deception.

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“If you don’t absolutely love Tobacco Road, you’re fired,” GOLF’s editor-in-chief told me with a laugh just before my tee time.

I kept my job, but then again, who wouldn’t? The place is impossible to hate. It’s golf’s biggest casino — slightly hokey, oddly self-aware, and purely entertainment. For every three sevens, there’s triple-seven hiding around the corner. It might be interpretationist golf, but who doesn’t love a good cover band?

IV. Smothered.

THERE IS at least one good thing that happens after 2:30 a.m., and it is called “Waffle House.” 

When the fine brothers of Beta Sigma Sigma Gamma stumbled into Waffle House on the morning of our arrival at Pinehurst Resort, we were firmly in the aforementioned sweet spot. It was 2:33 a.m., and we were on our way home from the local watering hole after a prolonged introduction with the region’s unofficial beer, Red Oak.

Twenty-five minutes later, we walked out with two shopping bags filled with waffles, loaded and smothered hashbrowns (surprisingly two different things), breakfast sandwiches, and eggs made every way. We tore into the food, sharing stories between bites from our rounds at Tobacco Road, our travels, and the previous two years of our lives. At one point, Tyler looked across the table.

“Can you believe we’re teeing off at Pinehurst in less than 12 hours?”

“Oh man,” I replied, remembering our scheduled 2:50 p.m. time on The Cradle. “I think it’s time for bed.”

We arrived at the Carolina Hotel 11 hours later with clubs, clothes, sleep deficits and ear-splitting headaches. We settled into our rooms just long enough to drop our bags and return to the car. It was time to play.

We giggled as we drove through the gates to the area labeled “Pinehurst Country Club” for the first time. A few seconds later, we grabbed our first glimpse at the property.

One member of our group gasped.

“Holy s—.”

Seven golf courses sat within eye’s reach, each more perfect than the last. Each perfectly maintained, each distinctly its own. Golfers whizzed by on carts, walked with trolleys, or slung clubs on their shoulders. Some listened to music, some held drinks in hand, but everyone — and I mean everyone — was smiling.

I wasn’t at a golf resort. I was in my own freakin’ nirvana.

By the time I reattached my jaw, it was time for our dinner reservation, a formal feast in the Carolina Dining Room. We gorged ourselves, completing our meal as only gentlemen could — with Key Lime Pie so large and delicious we nearly keeled over (order it and thank me later). We stumbled, or perhaps rolled, back to our respective rooms for the evening.

V. Playing Favorites

IF PINEHURST is the heartbeat of American golf, No. 2 is its carotid artery. The earth beneath No. 2 pulses with history, and in the early morning, the dew drips from the pines with the very lifeblood of the sport. On looks alone, it is enough to earn the distinction of being one of the few perfect routings on earth. Every blade of grass, every pine tree, every tee box and every delightfully evil turtleback green — it’s all perfect.

But somewhere around the 5th hole, it strikes you that your round has superseded its surroundings. In some small way, you begin to feel as if your name has been scrawled into the annals of golf history simply by being here. It’s an ephemeral, utterly intoxicating feeling; an emotion that leaves you floating through fairways and greens, simultaneously perplexed and awestruck.

It’s true, there aren’t any “signature holes” on No. 2. Rather, as one Pinehurst worker pointed out, there are 18 signature holes. How many courses can claim to leave you with a genuine sense of disappointment at the conclusion of the round? As far as I’m concerned, No. 1 on that list is No. 2 — even if my short game is unlikely to ever recover.

We left No. 2 with shattered confidence but spirits intact, making our way to No. 3 for the day’s second round. No. 3 is tiny, charming, and inviting — completely opposite to Ross’ work on No. 2. It’s the perfect spot for the emotional comedown that follows an all-time round. We spent most of our round as a sixsome, blasting music and trading laughs.

The sun had begun to dip below the sky when our round on No. 3 concluded. Mildly delirious and severely hungry, we dropped our bags at the clubhouse and headed into the village of Pinehurst for dinner.

If Pinehurst is the heartbeat of American golf, No. 2 is its carotid artery.

On the corner of a quiet street in the center of town sits the pub that is the area’s best-kept secret. Duggan’s is everything a post-round watering hole should be: dingy, dimly lit and delicious. In other words, it’s the perfect place for a good, old-fashioned golf debate.

“I’m just going to say it now,” Drew piped up from across the table. “No. 4 is the best course at Pinehurst. There’s just no way it could go any worse than No. 2.”

“I’m in on that take,” Tyler chimed in, fresh off a three-digit shellacking on No. 2.

“No way, man,” Connor chirped back.

It’s not clear whether Drew or Tyler paid off our starter the next morning on No. 4, but I wouldn’t put it past them. Particularly not after said starter matter-of-factly revealed No. 4 to be the “best course on property” at no one’s prompting. We chatted a bit more, and he whispered a secret.

“You ask a lot of folks around here their favorite course, folks who work here … they’ll say No. 4.”

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As it turns out, if you ask anyone about their favorite Pinehurst course, it’s likely you’ll get a fair amount of votes for No. 4. Gil Hanse’s 2015 renovation is a source of massive pride for Pinehurst, and for good reason. It’s excitable, walkable and playable, yet challenging enough to earn split duty for the 2019 U.S. Amateur.

No. 4 never stops being fun, from first tee box to 18th green — a point of emphasis for Hanse, who now owns the course’s design credit.

“I think what [co-designer Jim Wagner] and I tried to do is create great fun,” Hanse told me of his work on No. 4. “We wanted to make it memorable, and I think it is. I think people are enjoying the walk.”

As for whether it compares to No. 2? He gives a knowing chuckle.

“You know, No. 2 is The Mecca.”

If No. 4 is playful, its sister-course, No. 8, is peaceful. No. 8 is impossibly quiet, tucked away on its own piece of property that might as well be its own world. Bill, our shuttle driver, told us it was “the course that’d make us come back to Pinehurst.”

If he’d meant “in my nightmares,” perhaps he would’ve been right. My game did not travel with me on the short drive to No. 8, where Tom Fazio’s infuriatingly quick greens stupefied me into submission.

Still, it’s easy to see how people fall in love with No. 8. You feel as if you’re in your own world playing the course — completely removed from anyone or anything around you.

The 7th hole, a dogleg left par-4 over a cavern of sand, is when golfers first begin to see No. 8 for what it truly is — a little bit of everything.  It doesn’t grab you in the same way Nos. 2, 4 and The Cradle snatch your attention and later, your lust. But a trip to Pinehurst just isn’t complete without it.

Winner, winner!

Shortly after our round on No. 8 ended, we anointed Tim the winner of the first-annual Beta Sig Cup — handing off the hardware for his safe-keeping. The rest of us were forced to return only with our bags, a Brinks truck worth of Pinehurst gear and the warmth of our memories.

It was difficult to think of a better week. Hell, it was difficult to think of a better moment in our friendship. Well, except for the previous afternoon…

VI. Death (and other things)

TWENTY minutes after our brush with death, our sixsome finished our round at The Cradle.

The tiny nine-hole course became a beloved fixture of the golf world almost immediately upon its opening in 2017, and it’s easy to see why. Players are encouraged to walk barefoot, bringing only a handful of clubs and a single golf ball (anything more would be onerous). Music plays from every corner of the property, which also features the Pinecone, a bar-on-wheels tended by a transfusion-mixing superhero named Sheila. (Soon, the Pinecone will enter retirement, replaced by a full-time halfway house.) It’s impossible to leave The Cradle in a worse mood than you entered — even, it turns out, after a strangely dressed man’s bladed chip nearly brings your trip to an early end.

As we walked back in the direction of Pinehurst’s palatial clubhouse, a group of older men seated in Adirondack chairs overlooking the ninth (and final) green stopped us.

“Did you guys see Pajama Boy up there?”

“Excuse me?” I replied.

“This man, he was dressed in Pajamas or something, and he skulled a wedge that damn-near killed a group of guys.”

“We were that group of guys.”

Chris looked back at the course and flashed a smile.

“Guys, let’s grab a seat. I think I’ve got an idea.”

It took 30 minutes for Pajama Boy and his friends to make their way to the 9th hole, enough time for our party to recruit a few fellow bad actors. As Pajama Boy moved closer to us, Chris looked over at the small gallery we’d assembled.

“Alright, there he is. Everybody knows the plan, right?”

We nodded in his direction.

A few seconds later, Pajama Boy’s first playing partner stepped up to the tee box and placed his ball down. The 20 of us in Adirondack chairs showered him in thunderous applause.

Then came the group’s second player. The gallery followed suit, dousing the friend in a raucous cheer.

Then the third. More applause.

At long last, Pajama Boy stepped up to the tee box. He tipped his cap in our direction before reaching down to place his ball on the ground, preparing for another pleasant ovation to cap his round.

Instead, someone screamed.

“Oh s—! Not again!!!”

Down at the green, the gallery scattered, springing out of our chairs and barrel-rolling behind them as if to barricade ourselves from another wayward tee shot. We looked like we’d just crawled out of no man’s land, peering over the chairs gleefully. A handful of septuagenarians even joined in on the fun, giggling as they lumbered behind their seats.

As it turned out, our retaliatory prank had caused quite a commotion. A gathering of close to 100 on the patio behind us fell silent. Some golfers stared from hundreds of yards away. Others reflexively shielded themselves, too, not realizing it was all in jest.

Up at the tee box, Pajama Boy’s friends were beside themselves. They roared with laughter, doubled over as their poorly dressed friend turned a shade of magenta I’d never seen.

Miraculously, Pajama Boy summoned the wherewithal to strike his tee shot safely into a greenside bunker, and we returned to our seats. When his round ended, he came over and shook each of our hands.

“That was awesome, boys,” he said, his complexion still several shades rosier than it had been minutes before.

As Pajama Boy walked off into the distance, his friends stopped us.

“Seriously, thank you for that,” one of them said.

“We’re never going to forget that,” another friend chimed in. “And rest assured, we won’t ever let him forget it, either.”

Yes, it’s possible to die in golf heaven. But my god, whatever you do, don’t die of embarrassment.

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James Colgan

Golf.com Editor

James Colgan is an assistant editor at GOLF, contributing stories for the website and magazine. He writes the Hot Mic, GOLF’s weekly media column, and utilizes his broadcast experience across the brand’s social media and video platforms. A 2019 graduate of Syracuse University, James — and evidently, his golf game — is still defrosting from four years in the snow. Prior to joining GOLF, James was a caddie scholarship recipient (and astute looper) on Long Island, where he is from. He can be reached at james.colgan@golf.com.