Every friend group has a planner. Ours was John. For years, he organized golf trips for a group of four avid players, some with bonds reaching back to childhood. In early 2020, he began to orchestrate a long-discussed bucket-list trip: Six days in Pinehurst, N.C., a world-renowned golf destination that may have more good golf courses within a 15-mile radius, including the legendary Pinehurst No. 2, than anywhere in the world.
We were originally scheduled to go in May, and then again in early October, but the pandemic forced us to cancel both times. Finally, John rescheduled our trip for April 2021.
He died in late October.
After some soul-searching, we decided to honor his memory by going. And when the first of our two caddies introduced himself as John Ross on the first tee of Pinehurst No. 2 — our friend’s given name was Ross John — it seemed like it was meant to be.
We had chosen Pinehurst because of another Ross, famed golf course designer Donald Ross. Born in Scotland, Ross came to Pinehurst in 1900 at the behest of its founder, Bostonian soda fountain magnate James Walker Tufts. Donald Ross designed the first four courses at the Pinehurst Resort, including Pinehurst No. 2, arguably the best known of the approximately 400 courses he created.
Pinehurst No. 2 has hosted more golf championships than any other American course. What makes it so special are Ross’s trademark crowned, or turtleback, greens, which repel all but the best shots off the putting surface and into collection areas; this can leave diabolical recovery chips or putts to an uphill green that often return to where the previous shot started. I experienced this on the very first hole. On another, I putted completely across one green and down the other side.
Still, the course was a high point of our vacation. My goal was to play as many top courses in the Pinehurst area as we could, and we ended up playing 11 during our six-day stay. This part of central North Carolina is known as the Sandhills, a result of ancient sand dunes formed by the receding oceans from thousands of years before. The result is sandy soil ideal for golf courses, one reason there are more than 40 in the area.
My trip started with a six-hour drive from Takoma Park, Md, to the Raleigh-Durham airport to pick up my high school friend Greg, who was arriving on a 1:30 p.m. flight. My other high school buddy, Steve, was arriving at 9:30, so Greg and I decided to squeeze in an unplanned round at the deceptively challenging Hillandale Golf Course in Durham, N.C., to pass the time while waiting for Steve’s flight.
Afterward we drove an hour to the Springhill Suites by Marriott in Pinehurst, our home for the first three nights. (We started our Pinehurst package on day four, and stayed at condos near the resort, which offers five different lodging options.) The first official day of our trip had us playing the sister courses Pine Needles and Mid Pines, both designed by Ross in the 1920s and both in Golf Digest’s list of top 25 courses in North Carolina. We quickly got a sense for what we were in for the rest of the week — challenging and very fast greens, plenty of sandy waste areas, longleaf pines framing most holes and a feeling of being transported back to an earlier, simpler time. From hitting balls on the Pine Needles’ pristine driving range at 7 a.m. to finishing our 36th hole of the day on the 18th at Mid Pines with the beautiful backdrop of the century old, Georgian-style Inn at Mid Pines, it was a great way to begin.
Tired and hungry, we got our first taste of North Carolina cuisine at Smithfield’s Chicken ‘N Bar-B-Que, where we ordered barbecue sandwiches with coleslaw, baked beans and hush puppies with honey butter.
The next day’s first course, Dormie Club, was scheduled to turn private just days after we played it, and we felt like members for the day at the pristine and beautiful course. The same could not be said for our afternoon round. Tobacco Road in nearby Sanford, N.C., is a course you have to see, and experience, to believe. Designer Mike Strantz combined his two passions, art and golf, to create an extreme, visually striking and intense course that is the polar opposite of the minimalist Ross-designed courses we played for much of our trip.
Consider the first hole: Players have to hit between two 40-foot high man-made hills to reach the fairway. There are more sandy waste areas here than on any course I’ve ever seen, and with the wind blowing a steady 25 mph, we literally got a taste of them as well. (Speaking of which, be sure to order the barbecue sandwich in the clubhouse.) This is a course you’re going to feel strongly about one way or the other. I’m glad we tried it, but was happy to get on more familiar — and level — footing the next day.
From there it was on to the Pinehurst Resort. We started with Pinehurst No. 1, the first course built at Pinehurst and another Ross design, before playing No. 9, a Jack Nicklaus layout, in the afternoon. Both were good courses, but we were thinking ahead to playing Pinehurst No. 2 the next morning.
Our Pinehurst No. 2 caddies John, who is 80 and has been caddying at Pinehurst since he was 13, and 25-year-old Derek, did much more than carry our bags (no carts are allowed on No. 2) and read our putts. John told us his first tip at Pinehurst, in 1954, was a nickel (Pinehurst Resort recommended we tip each caddie a minimum of $40, on top of a caddie fee of $65, which was money well spent), and Derek told us his biggest tip was $600. “That guy was a freaking unicorn,” he said with a smile.
Despite the storied challenge of the greens, No. 2 was very playable, and no one in our foursome lost as much as one ball. A cool feature to know is that Pinehurst gives anyone who gets a 2 on any hole on No. 2 a commemorative coin. We came close several times, but did not succeed.
We relived our No. 2 adventure immediately after with lunch at the Deuce, a casual, pub-style eatery whose outdoor seating overlooks the 18th green. After lunch, I spent time touring the Pinehurst Resort clubhouse, which resembles a golf museum, complete with a gift shop. The display that caught my attention featured charismatic Payne Stewart, winner of the 1999 U.S. Open played at No. 2.
Stewart, who died in a plane crash in October of that year, is a larger-than-life presence at Pinehurst thanks to the bronze statue of his dramatic fist-pump celebration on the 18th green that sits 50 yards from that spot.
Greg and I then went to play the Cradle, Pinehurst’s nine-hole short course just a few steps from the clubhouse. So named because Pinehurst is considered the home, or cradle, of American golf, the Cradle had a relaxed, laid-back vibe. Music was piped onto the course, and drinks were available at the vintage beverage cart located nearby, where taking a break to sit in Adirondack chairs was encouraged.
We reserved caddies again the next morning for playing Pinehurst No. 4. Caddie Greg Tew, whom I had requested in advance on a friend’s recommendation, was friendly, knowledgeable and unfailingly positive. It was our conversation on the 14th tee — a long par 3 with water in front and left of the green, with the pin on the left side — and what happened next that I will always remember.
When handing me my 5-iron, Greg said, “We’ve been talking about holes in one, but this is not the place for that.” He said to hit it well right of the hole, my best chance to avoid the water. I hit my best shot of the day, which started right but kept moving left. The ball ended up about 10 feet from the cup. Greg broke into a big laugh and gave me a fist bump as we walked to the green.
That afternoon we played Pinehurst No. 7 in the rain, the only bad weather we encountered. But we ended our trip on a brighter note with a Sunday-morning round at Pinehurst No. 8. Known as the Centennial for opening 100 years after Pinehurst’s founding in 1895, it deserves its billing as one of the Pinehurst’s best three tracks, with No. 2 and No. 4, and is the most underrated.
Our Pinehurst Resort package included breakfast and dinner at a variety of locations. We chose the historic Carolina Hotel, which opened in 1901 and exudes Southern charm, to start our days, and had dinner at a different restaurant each night. Among them were the Pinehurst Brewing Company, a converted steam plant with valves and pipes serving as table legs and light fixtures, and the Tavern at the Holly Inn, Pinehurst’s oldest hotel, whose antique bar was imported from Scotland. As my friend Steve said, “We birdied breakfast and dinner every day.”
It was the golf trip of a lifetime, just as John planned, and more than once we toasted the memory of our absent friend, knowing he would have enjoyed every minute of it.
Springhill Suites Pinehurst Southern Pines
10024 U.S. Highway 15/501, Pinehurst, N.C.
This hotel’s best feature is that it is centrally located for easy access to all of the Pinehurst-area courses. It also offers grab-and-go food offerings, including fresh fruit, yogurt, breakfast sandwiches, juice, water and coffee, which is perfect for breakfast before golf, snacks during your round and hydrating before bed. Rates from $120 per night and vary by time of year.
80 Carolina Vista Drive, Pinehurst, N.C.
Pinehurst Resort offers a variety of golf packages. The most popular is the Donald Ross package that includes a two-night stay and three rounds of golf on any of Pinehurst Resort’s nine courses, along with breakfast each morning. Note that there is a $195 surcharge to play Pinehurst No. 2, and caddie fees are not included. Through Sept. 8, rates from $1,038 per person. Rates are highest in the fall and spring, and lowest during the winter. Rates include cart fee, club storage, unlimited use of golf practice facilities, shuttle service to the resort, access to the fitness center, pools, bikes and afternoon tea. Rates subject to tax and resort service charge.
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