Thoroughbred Horse Races Worth Traveling For
Nothing beats the excitement of the Kentucky Derby or the tailgating traditions of Southern steeplechases. If you're looking for an unforgettable equestrian experience, these famous horse races are worth traveling for. Image: Louisville Tourism
The horse racing experience begins long before the horses leave the starting gate, blending sport, fashion, food, and socializing into every event. Whether you’re watching thoroughbreds thunder down the stretch or are simply soaking up the atmosphere with friends, these races around the country offer unforgettable experiences that are well worth the trip.
Kentucky Derby
Where: Churchill Downs, Louisville, KY
When: First Saturday in May
More Info: kentuckyderby.com
The Kentucky Derby is hailed as “the most exciting two minutes in sports.” As the first leg of the Triple Crown, it is the most famous horse race in the country, featuring elite three-year-old thoroughbred horses. Though the “Run for the Roses” only lasts about 120 seconds, the buildup begins weeks in advance.
Festivities kick off with Thunder Over Louisville (said to be the largest annual fireworks show in North America), and include a variety of other events, parties, and traditions. If you’re going to attend, book accommodations early — and don’t forget to plan your outfit!
Preakness Stakes
Where: Pimlico Race Course, Baltimore, MD
When: May, two weeks after the Kentucky Derby
More Info: preakness.com
The Preakness Stakes is the second leg of the Triple Crown and measures 1.25 miles — slightly shorter than the Kentucky Derby. It is often called “The Run for the Black-Eyed Susans,” with the race’s winning horse draped in a garland of Viking daisies dyed to resemble Maryland’s state flower, the black-eyed Susan (which does not bloom during the race’s May date).
The winning owner receives the Woodlawn Vase, an 1860 Tiffany & Co. creation so valuable it rarely leaves the Baltimore Museum of Art. A replica is typically presented at the track.
Belmont Stakes
Where: Belmont Park, Elmont, NY
When: Three weeks after the Preakness Stakes
More Info: nyra.com
The final and longest leg of the Triple Crown, the Belmont Stakes, is 1.5 miles long. It is also the oldest of the three Triple Crown races and is dubbed “The Test of the Champion.”
The Belmont’s signature flower is the white carnation, which is draped over the winning horse in a blanket similar to the roses at the Kentucky Derby and black-eyed Susans at the Preakness. With the track about an hour away from NYC, a trip to the Belmont Stakes can easily be paired with a weekend of exploring Manhattan.
Keeneland Spring Meet
Where: Keeneland Race Course, Lexington, KY
When: April
More Info: keeneland.com
Typically running for 15 to 16 race days, this meet kicks off the spring racing season in Kentucky and includes the Blue Grass Stakes, a prestigious prep race for the Kentucky Derby. All races take place at Keeneland Race Course, considered by many to be one of the most scenic tracks, with limestone architecture, tree-lined grounds, and historic charm.
Don’t miss the elevated racetrack dining options, including bourbon-based cocktails, local barbecue, and the famous Keeneland bread pudding. A little over an hour’s drive from Louisville, the meet makes for a fun day trip from Louisville leading up to the Kentucky Derby.
Iroquois Steeplechase
Where: Percy Warner Park, Nashville, TN
When: Second Saturday in May
More Info: iroquoissteeplechase.org
Unlike traditional flat racing, steeplechase races require horses to jump a series of fences while racing across a long grass course — and Iroquois Steeplechase is one of the South’s biggest steeplechase races. It first ran in 1941 and doubles as a major fundraiser, benefiting Monroe Carell Jr. Children’s Hospital at Vanderbilt and other local nonprofits. Groups often gather in tents and tailgate areas to enjoy food and drinks throughout the day.
Fashion is part of the tradition, too, with spring styles similar to what’s seen at the Kentucky Derby. Because the race is close to downtown Nashville, visitors can easily turn the event into a full weekend trip, combining the steeplechase with live music, restaurants, and nightlife in Music City.
Carolina Cup
Where: Springdale Race Course, Camden, SC
When: Late March or Early April
More Info: carolinacup.org
Often described as “the Kentucky Derby of steeplechase tailgating,” the Carolina Cup is a mix of horse racing, fashion, and Southern springtime celebration. Running since 1930, the event typically draws tens of thousands of spectators, making it one of the biggest steeplechase gatherings in the country.
Tickets often sell out months in advance, so plan early, based on the experience you’re looking for: infield tailgating spaces for a more social atmosphere; grandstand seating for the best race views; or VIP hospitality tents for a truly elevated occasion.
Virginia Gold Cup
When: Early May
Where: Great Meadow, The Plains, VA
More Info: vagoldcup.com
First run in 1922, the Virginia Gold Cup is set on a sprawling, 380-acre equestrian complex in Virginia’s Piedmont region. It draws tens of thousands of attendees every year, and like many other Southern steeplechases, elaborate tailgating parties are part of the experience.
Visitors can expect to see several steeplechase races throughout the day, with horses jumping timber and hurdle fences across the course. Located roughly 45 minutes away from Washington, DC, the Virginia Gold Cup makes for an easy day trip while visiting the nation’s capital.
Aiken Steeplechase
When: March
Where: Bruce’s Field, Aiken, SC
More Info: aikensteeplechase.com
Set in a town famous for the winter training of thoroughbreds and steeplechase horses, the Aiken Steeplechase is organized by the Aiken Steeplechase Association, which distributes proceeds to a wide range of local charities each year. Here, the Southern steeplechase trailgating tradition continues, with groups bringing decorated tents, picnic spreads, and lawn games to the grounds.
Take some time to explore the town while you’re there, making stops at the Aiken Thoroughbred Racing Hall of Fame and Museum, local horse farms, and downtown shops and restaurants.
Steeplechase of Charleston
When: November
Where: Stono Ferry Race Course, Charleston, SC
More Info: steeplechaseofcharleston.com
Located in the Lowcountry, Stono Ferry Race Course offers marsh views, oak trees, and open fields, creating a relaxed outdoor atmosphere that sets it apart from traditional, stadium-style racetracks. Though the fall event is significantly more laid-back than spring races like the Kentucky Derby, tailgating is still a big part of the experience, with spectators setting up tents and spreads of food and drink to enjoy between races.
Because Charleston is such a popular travel destination, it makes for an easy day trip while spending some time exploring the city’s historic district, restaurants, and waterfront areas.
Pegasus World Cup
When: January
Where: Gulfstream Park, Hallandale Beach, FL
More Info: pegasusworldcup.com
Taking place every January, the Pegasus World Cup is one of the first major racing events of the year, blending racing with concerts, DJs, and luxury hospitality areas for a festival-style experience. Established in 2017, it’s one of the newest racing traditions, with sunny skies and 70-degree weather being a big draw.
Though it’s less than a decade old, the Pegasus attracts celebrities, athletes, and top thoroughbreds from around the world. Don’t miss the Carousel Club, an on-site open-air venue that features music performances, cocktails, and a high-energy party atmosphere throughout the day.
Happy race watching!
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To find more incredible Southern events, visit our Events Calendar.
Lennie Omalza
Originally from Hawaii, Lennie Omalza is a Louisville-based freelance writer of over 18 years. Lennie is a yoga-loving foodie who travels as often as she can and enjoys writing about food, homes, and weddings. You can find more of Lennie's work at Eater, Hawaii Home & Remodeling, and The Louisville Courier-Journal.