One May day in 1875, 10,000 cheering horse racing fans at Kentucky’s Louisville Jockey Club, now Churchill Downs, marveled as African American jockey Oliver Lewis brought his chestnut colt Aristides neck-and-neck with Volcano on the homestretch, the pair surging ahead of the pack of lightning-fast thoroughbreds.

The horses thundered in tandem at such breakneck speed, it almost seemed they could take flight like the mythical Pegasus, but in the last few seconds, Aristides broke away and bolted to victory in the inaugural Kentucky Derby.

That was the first of many history-making moments that have transpired in the last 150 years at this venerated racetrack that is home to what’s known as the “most exciting two minutes in sports.” As the oldest continuously held sporting event in the United States celebrates its sesquicentennial, there’s no better time to take a deep dive into Derby history and catch a glimpse of how the race is looking to the future.

The grand spectacle that is the Kentucky Derby is more than the country’s most prestigious horse race. Its magic emanates from the pageantry that plays out in the shadow of the track’s regal twin spires. Everything from the crowd singing “My Old Kentucky Home” to the red-coated bugler playing “Call to the Post” to the champion horse being blanketed with red roses are part of the enduring legacy of the Kentucky Derby.

Credit: Handout

Credit: Handout

Churchill Downs, a National Historic Landmark, has many long-standing traditions, but it’s not frozen in time. The biggest change in decades will be unveiled at the 150th Run for the Roses on May 4.

A $200 million redesign of the saddling paddock where the feisty 3-year-old thoroughbreds are held before the race has been underway for more than a year. This treasured area of the track will more than double in size, expanding from 5,000 to 12,000 square feet. The stalls will be moved beneath the twin spires for what will surely become an iconic view.

The expansion creates 3,600 premium seats and adds space for 3,250 standing-room-only ticket holders.

Edward Bowen, 81, a retired thoroughbred racing journalist and historian who covered 52 consecutive Kentucky Derbies from 1964 to 2015, has a special appreciation for how the expansion will enhance Derby Day festivities.

“Having watched the Derby on black-and-white TV screens since childhood, I had a sense of drama connected to the saddling area of the 1950s,” Bowen said. “When I began having the opportunity to see the race in person, I realized how few people at the track had the opportunity to actually see into the saddling enclosure.”

The saddling paddock is sort of like a locker room for horses, because it is where the equestrians get their game face on before the biggest race of their career. Now, it will be one of the first things fans see when they pass through the gate.

On days when there’s no live racing at Churchill Downs, visitors can take a 90-minute Superstars and Spires Tour for a behind-the-scenes peek at private areas such as the exclusive Millionaires Row where celebrities and dignitaries in extravagant hats sip mint juleps with an enviable view of the finish line.

On the second floor of the clubhouse are the eye-catching Peb murals, named for Pierre “Peb” Bellocq, the cartoonist who created them. A 36-foot mural features humorous caricatures of every Derby-winning jockey from 1875 to 2004, including the late Bill Shoemaker, the 4-foot-11-inch force of nature who won the Derby four times and is widely heralded as one of the greatest jockeys of the 20th century.

Credit: Wesley K.H. Teo

Bowen witnessed first-hand many of the Derby’s most historic moments, including the time legendary thoroughbred Secretariat became the first to run the 1.25-mile race in under two minutes. It was the first victory in Secretariat’s Triple Crown sweep. The Triple Crown is a series of horse races that includes the Kentucky Derby, the Preakness Stakes and the Belmont Stakes, in that order, and is the ultimate prize in horse racing.

To learn more about Secretariat, visit the Kentucky Derby Museum adjacent to Churchill Downs. “Secretariat: America’s Horse,” the newest permanent exhibit, chronicles the racing career of the powerful colt nicknamed “Big Red” because of the color of his coat.

Each of the three Triple Crown races Secretariat won are shown on a 10-foot screen, allowing fans, some of whom weren’t around during his lifetime, to cheer on the fastest racehorse in history — thrilling even though they know the outcome. At the Belmont Stakes in New York, Secretariat was so far ahead, it was as though the trailing pack was trying to outrun a freight train. As announcer Chic Anderson put it, he moved “like a tremendous machine,” winning by a phenomenal 31 lengths, the highlight of his record-breaking career.

Secretariat’s trailblazing owner Penny Chenery is also honored. She became known as the “First Lady of Racing” in a male-dominated sport.

To understand the early years of the Derby, stroll through the “Black Heritage in Racing” exhibit that chronicles the legacy of Kentucky’s Black equestrians who dominated the sport in the latter half of the 19th century. They worked as jockeys, breeders, trainers and grooms, and were considered some of the best horsemen in the world. The rise of Jim Crow laws that enforced racial segregation in the Post-Reconstruction South forced them off the track, and for decades, their contributions to the sport were forgotten.

Artifacts include the purse that held celebrity jockey Isaac Burns Murphy’s 1891 Derby winnings. Murphy, the son of a former slave, was the first jockey to win the Derby three times. If he were around today, he would probably be celebrated as a superstar athlete with millions of TikTok followers.

Whether you attend the race or plan your visit when the ponies aren’t running, a Louisville getaway will inspire reverence for the Bluegrass State’s thoroughbred racing industry and the generations of equestrians who shaped its most famous event.

IF YOU GO

Where to Stay

The Myriad Hotel. A new boutique hotel in a converted disco ball factory. $1,000 per night Derby weekend. Minimum three-night stay. Ultimate Kentucky Derby Dream Package includes three rooms for a three-night stay, a six-person box to the Kentucky Derby and The Oaks race the previous day, and dinner at Paseo. $35,000. 900 Baxter Ave., Louisville, Kentucky. 502-632-7931, www.myriadhotel.com

Hotel Distil. Boutique hotel in a former distillery. $3,500-$8,000 per night Derby weekend. Minimum three-night stay. 101 W. Main St., Louisville, Kentucky. 502-785-0185, www.hoteldistil.com

Where to Eat

Buck’s Restaurant. Upscale restaurant serving steaks, seafood and more. Entrees $28-$130. 425 W. Ormsby, Louisville, Kentucky. 502-637-5284, www.buckslou.com

Decade. New restaurant serving elevated Southern cuisine. Entrees $28-$51. 1076 E. Washington St., Louisville, Kentucky. 502-749-0110, www.decaderestaurant.com

Activities

Kentucky Derby. May 4. $115 and up, infield. $650 and up, reserved seats, sold as a two-day package for the Derby and Kentucky Oaks. Churchill Downs, 700 Central Ave., Louisville, Kentucky. www.churchilldowns.com

Kentucky Derby Museum. $25. $20, Superstars and Spires Tour. 704 Central Ave., Louisville, Kentucky. 502-637-1111, www.derbymuseum.org

The Kentucky Derby Festival. A multitude of ticketed events including a rooftop party, bourbon tasting, wine fest, a parade and take place during the two weeks preceding the race. Venues and ticket prices vary. www.kdf.org