Legends of the Pines

Legends of the Pines

By Nicole Letts

There are more than a few legends who once walked the grounds of Pinehurst, North Carolina. As a town established in 1895, numerous storied guests and residents have roamed the streets. From world-famous golfers to sharpshooters, these famous men and women impacted history both in the area and well beyond it.

Annie Oakley

A storied markswoman, Annie Oakley had already wowed audiences across the country before landing at Pinehurst. She made a name for herself in Buffalo Bill’s Wild West Show and was hired alongside her husband, Frank Butler, at the Carolina Hotel. Oakley taught shooting lessons while Butler managed the Pinehurst Gun Club. Her tenure began in 1915, and during her time in Pinehurst, Oakley not only befriended some of the area’s social elite but also taught women how to handle and shoot guns. Her stint allowed her to show off her skills while enjoying a respite from her celebrity status.

Frederick Law Olmsted

When James Walker Tufts imagined a plan for his visionary health resort in the Sandhills, he dreamed of a place that was as beautiful as it was restful. He turned his sights toward other great developments, specifically those helmed by celebrated designers. Frederick Law Olmsted was hired. Olmsted had already been attached to successful projects like New York’s Central Park and Asheville’s Biltmore Estate, and his reputation preceded him. He, along with Warren H. Manning, developed a cityscape with a curvilinear and concentric street system. The results were ample greenspaces that emphasized the area’s beauty. Today, Pinehurst remains the only National Historic Landmark in America, whose landscape has contributions from both Frederick Law Olmsted, Sr. and Warren H. Manning.

Bobby Jones

Bobby Jones is often closely associated with golf in Atlanta, but did you know he had a history at Pinehurst, too? Jones not only played the course a few times, but he also inadvertently inspired the reconstruction of Pinehurst No. 2. Legend has it that Jones had unofficially hired Donald Ross to design a nearby notorious course, Augusta National. However, after befriending Alister MacKenzie during a stint in the Monterey Peninsula, Jones hired MacKenzie to design the new course instead. The snub left Ross ready to make his prized course the gem of American golf. He added the fourth and fifth holes, rebuilt and re-contoured all the greens, replaced the putting surfaces with Bermuda grass, and added new tees and bunkers. We can thank Jones for motivating Ross to develop Pinehurst into what it is today.

Payne Stewart

Perhaps the most well-known figure in Pinehurst’s history is Payne Stewart who famously won the 1999 U.S. Open at Pinehurst. The competition called “The Duel” came down to Stewart nailing a 15-foot par putt to beat Phil Mickelson. The victory is not only cemented in hearts and minds but in bronze, too. A statue depicting Stewart’s excitement is perched about 50 yards off the 18th green at Pinehurst No. 2. At any given time on any given day, passionate golfers and fans circle around the statue to snap their photos. Tragically, Stewart was killed in a plane crash just a few months after his win, but his memory and legacy live on.

Maureen Orcutt

While Maureen Orcutt might not be as well known in history as her male counterparts, her mark on Pinehurst certainly rivals them. Orcutt was a renowned amateur golfer who dominated the game at Pinehurst. In fact, she won the North and South Women’s Amateur at Pinehurst Resort back-to-back in 1931, 1932, and 1933. Thirty years later, she returned to Pinehurst and won the North and South Senior Woman’s Amateur three times in a row again in 1960, 1961, and 1962. Personally, she was only the second female sports reporter for The New York Times.


Nicole Letts is an Atlanta-based freelance journalist focused on the modern American South. Some of the country’s top magazines and digital publications have published her work, including AAA Explorer Alabama, Architectural Digest, BBC Travel, Fodor’s Travel, Garden & Gun, Good Grit, Southern Living and many more. She is also the author of the new book, Unique Eats and Eateries of Alabama. When she’s not writing, you can find stitching cheeky needlepoint canvases or perusing local antique shops for her online business, Grandmillennial Shop.



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