Nestled on Versailles Road is a gorgeous expanse of racetrack, its grandstand rising from the greenery of the Bluegrass as cars speed toward the welcoming streets of Lexington, Ky. With its classic lines and hand-chiseled limestone, Keeneland Race Course is a beacon of what racing can be, a celebration of the horse as well as a home for the sport’s fans, its focus on the past, present, and future all at the same time.

This former family farm has evolved into a showplace for the sport of horse racing, a destination for fans from across the world. Since its opening day in 1936, Keeneland has become the home to an important Kentucky Derby prep, a state-of-the-art sales organization, and several of the calendar’s most important stakes races for multiple divisions, all thanks to the vision of a few breeders and owners who wanted to preserve the sport in its Bluegrass cradle.

The Kentucky Association Race Track

Lexington has long been home to horses and racing, dating to the early years of American independence. James Herrod founded one of the area’s first racetracks in 1780, and in 1826, area political and civic leaders Henry Clay, Dr. Elisha Warfield, Thomas F. Marshall, and Jesse Bledsoe collaborated to create the Kentucky Racing Association. Two years later, they opened a racetrack at what is now the east end of 5th Street at Race Street. Eventually growing to cover about 65 acres, the track featured a one-mile dirt oval, grandstand, clubhouse, and barns, and was a key part of Kentucky racing for a century.

Financial issues plagued the track in the late 19^th century, resulting in the track’s sale, and then again in the early 1930s as the Great Depression took its toll on the country. Dilapidated and failing, the Kentucky Association racetrack closed for good in 1933 and then was torn down in 1935. The track where famed jockey Isaac Murphy won his first race and where Man o’ War paraded before going to stud in 1921 would soon give way to a new racetrack in Lexington, a historic venue that would become a destination for racing fans all over the world.

John Oliver “Jack” Keene (1870-1943)

John Oliver “Jack” Keene (Keeneland Library Leach Collection)

John Oliver “Jack” Keene’s family estate near Lexington had been in his family since the late 18^th century, after Patrick Henry, governor of Virginia, gave his ancestor Francis Keen nearly eight thousand acres in what would become Kentucky. The family built their home, now known as Keene Place, in 1805, and started breeding and racing horses, a pursuit that trickled down through the generations to Jack.

A natural horseman, his career started at the Kentucky Association track before moving first to Chicago and then California, where he met owner Jimmy Fletcher. Soon he was taking his talents across the Pacific, to Japan and then Russia, as Fletcher expanded his racing interests internationally. Keene returned home to the United States and his Keeneland Stud, despairing at the state of the Kentucky Association racetrack. Not one to sit idly by, he started building a racetrack on his own land in 1916, with the intention of making it a private training and racing space, a model for other such facilities across the country. He laid out a 1 1/16-mile track and then built a barn that also would serve as a home, complete with living quarters, ballroom, dining room, and more. His time in Russia also inspired him to add an indoor training space next to the “barn.”

The exteriors were built using limestone cut in ‘two-to-one’ pattern reminiscent of buildings Keene had seen overseas, a style that has become a signature of Keeneland Race Course. He funded the construction of his vision through sales and racetrack earnings but never had enough money to finish his project. By 1935, he decided to sell Keeneland Stud and its 147 acres to a committee of horsemen who wanted to bring another racetrack to the Lexington area after the Kentucky Association facility closed. The group, headed by Hal Price Headley of Beaumont Farm, purchased Keeneland for $130,000 on Aug. 29, 1935.

Thus began the transformation of Keene’s pet project into one of America’s most beautiful racing locales, a place where the sport and its many facets thrive.

The Keeneland Association

Opening day at Keeneland in 1936. (Keeneland Library Collection)

When the Kentucky Association racetrack closed in 1933, the Lexington area was bereft of a racetrack for the first time in more than a century. The state also had Churchill Downs in Louisville, Dade Park in Henderson, and Latonia in Covington, but the breeders and owners who all called Lexington home wanted to continue racing in Central Kentucky.

Together, they formed the Keeneland Association “to create a model race track to perpetuate and improve the sport and to provide a course that is intended to serve as a symbol of the fine traditions of Thoroughbred racing.” They were set up as a nonprofit, money made through racing and later sales supporting purses and making this new racetrack a destination for many of the sport’s biggest names.

After purchasing Keeneland Stud, the Keeneland Association set a goal of October 1936 for its opening meeting at Keene’s former farm. Construction began on an outdoor saddling paddock and barns; an odds totalizator board went up in the infield as both the grandstand and clubhouse were outfitted with the latest parimutuel equipment for bettors, the first of their kinds in Kentucky. Opening day was set for Oct. 15, with a card of seven races cued up for the crowd of 8,000. Future Hall of Famer Myrtlewood won the six-furlong Keen Handicap on opening day as Jack Keene looked on, celebrating the transformation of his farm into a beautiful home for the sport. Two days later, Myrtlewood won the inaugural Ashland Stakes, now a Grade 1 fixture for the 3-year-old filly division.

The Keeneland paddock in 1950. (Keeneland Library Meadors Collection)

The following spring, Keeneland celebrated its first spring meeting and would continue to run its Spring meet even through World War II. Because of its location, the racetrack was not allowed to race during wartime so the Keeneland Association leased Churchill Downs and held spring meets there from 1943-1945. Racing returned to Keeneland in spring 1946 along with another technological innovation, the photo-finish camera. In 1997, the track would add a public address system, breaking with 60 years of tradition as it became the last racetrack in the country to broadcast race calls.

The first four years of Keeneland’s history introduced two other famed parts of its mission. The first was horse sales: the track hosted its first auction in the paddock in April 1938. The following year, William Arnold Hanger donated his 2,300-volume library of rare books on Thoroughbreds, the seed for the Keeneland Library. Soon, other luminaries gifted their own collections of both books and ephemera as the newly founded resource found its home in the track’s grandstand until 2002, when a dedicated building opened on “The Hill” near the sales ground and racetrack. The Keeneland Library currently stands as the world’s premier repository for materials related to the sport, housing vast collections of photographs, books, and more, all available to the public at no cost and playing host to events like its Lecture Series and special exhibits like the Heart of the Turf, which celebrates the lives and contributions of African Americans to the sport.

In August 1943, Keeneland hosted its first yearling sale as Fasig-Tipton set up a tent in the paddock to sell 312 horses, including a colt by Sir Gallahad III out of the mare One Hour purchased by Fred W. Hooper. That colt, Hoop Jr., would win the 1945 Kentucky Derby. The Breeders’ Sales Company leased facilities at Keeneland for its first summer yearling sale, later known as the July Selected yearling sale, in 1944. Two decades later, Keeneland Race Course, the Breeders’ Sales Company, and the Keeneland Association all merged into a single corporation with three divisions: auction, racing, and publicity/public relations.

The sales division of Keeneland now hosts five sales yearly, starting with its January horses of all ages sale through the November breeding stock sale in November. The list of horses, including Hall of Famers, who have gone through the sales ring at Keeneland reads like a veritable list of the sport’s greats: Kentucky Derby winners like Jet Pilot, Dark Star, Venetian Way, Alysheba, Real Quiet, and Animal Kingdom; champions like Wajima, The Minstrel, Nureyev, Risen Star, Curlin, and Zenyatta; Epsom Derby winner Golden Fleece; and many more. In all, winners of 24 Kentucky Derbys, 27 Preaknesses, and 23 editions of the Belmont Stakes have sold there as have winners of the Prix du Jockey Club and the Irish and English Derbys.

From Jack Keene’s vision has emerged a venue for the sport’s best and brightest, whether they are passing through the sales ring or sailing past the finish line in one of the track’s many stakes.

A Destination for Greatness

Arts and Letters winning the 1969 Blue Grass Stakes. (Keeneland Library Wyatt Collection)

Designated a historic landmark in 1986, Keeneland has evolved from Keene’s multi-use clubhouse to a modern racing and sales facility. Spanning a thousand acres, the track has played host to an actual monarch in Queen Elizabeth II, who visited in 1984, and equine ones, including Zenyatta, who said goodbye to her racing career with a last hurrah on a bitterly cold night in at the sales pavilion in 2010. The limestone façade and iron gate posts from the original Kentucky Association racetrack mark this space as an idyllic spot to watch a day at the races. That combination has made Keeneland a destination for many a racing fan as have great stakes like the Blue Grass Stakes, one of the premier Kentucky Derby prep races; the Breeders’ Futurity and Alcibiades Stakes, both important tests for 2-year-olds; and Grade 1 stakes for older horses like the Madison and the Maker’s Mark Mile.

Nearly 90 years of renovations and upgrades have turned the original Keeneland into an expansive facility. The track’s reputation as a sublime racing experience has brought it into the Breeders’ Cup fold as the track hosted the World Championships for the first time in 2015 and twice more since then in 2020 and 2022. The largest ever one day’s attendance at the track, 50,155 on Breeders’ Cup Saturday, Oct. 31, 2015, when American Pharoah put the cherry on top of his Triple Crown season with a win in the Breeders’ Cup Classic. No doubt the Breeders’ Cup will once again come to Keeneland in the future.

Born of the vision of one breeder/owner and his contemporaries, Keeneland Race Course stands as a living testament to the rich heritage and enduring spirit of racing in Kentucky. From its founding in 1936 to its status as one of the sport’s most revered venues, this track has seamlessly blended tradition with innovation, preserving the pageantry of racing while embracing modern advancements. Its yearly Spring and Fall meets, world-renowned sales, and commitment to equine welfare ensure its continued influence on the sport as a whole. Keeneland stands a symbol of excellence, where history and the future stride together, captivating fans and horsemen alike for generations to come.

Ray Waldron, Major Louis A. Beard and Hal Price Headley at Keeneland in 1940. (Keeneland Library Collection)