May in Nashville is all about hats, hooves, and high spirits! As the city shakes off the chill of spring, horse season takes center stage—with steeplechase races, Derby watch parties, and all the Southern charm you can handle. Whether you’re heading to the iconic Iroquois Steeplechase or dressing up just to sip a mint julep in style, there’s something magical about this time of year. Think big hats, bold sundresses, and boots made for more than just walking. From themed cocktails and Derby pie to outfit inspo and party picks, this guide rounds up everything you need to gallop into the season with flair.

Option 1: Off to the Races: Nashville’s Iconic Steeplechase

The Iroquois Steeplechase is more than just a day at the races—it’s a Nashville tradition that blends Southern charm, high fashion, and heart. Held each May at the scenic Percy Warner Park, this all-day event features thrilling steeplechase races, vibrant social scenes, and a chance to give back. With proceeds supporting Monroe Carell Jr. Children’s Hospital at Vanderbilt and other local nonprofits, it’s a celebration with purpose. Steeplechase fashion is a show of its own—think bold hats, breezy fabrics, and shoes made for grassy strolls. Whether you’re a longtime attendee or gearing up for your first time, there’s something special about the excitement that builds around this unforgettable spring day in Nashville. Get ready to dress up, cheer loud, and soak in one of the most fun and festive events of the season! 

• Saturday May 10, 2025
• Percy Warner Park
• Buy your tickets here: https://www.iroquoissteeplechase.org/

Option 2: Derby Day, Nashville Style: Where to Watch, Sip & Celebrate

If you can’t make it to Churchill Downs, Nashville’s got you covered with some seriously stylish Derby watch parties. The Derby Party at The Union Station Nashville Yards on May 4th is the place to be for luxe vibes—think Southern fare, live music, Mint Juleps, and a best-dressed contest in one of the city’s most iconic venues. Looking for something a bit more laid-back? Head to Von Elrod’s for their Talk Derby to Me bash, where you’ll find brunch, big hats, and free fun for all ages. Want to get hands-on? Liquor Lab Nashville is offering a Derby-themed cocktail class on May 3rd and 4th, perfect for learning how to shake up your own winning drinks. No matter your style, there’s a way to celebrate the Derby in true Nashville fashion—big hats, bold sips, and good vibes guaranteed! 

Learn more here: https://nashvilleguru.com/134088/derby-parties-in-nashville

Option 3: What to Wear for Steeplechase in Nashville or the Kentucky Derby: Tailgating in Style at the Races

Horse race season is as much about the fashion as it is the thrill of the track, and whether you’re heading to Nashville’s Iroquois Steeplechase or traveling to Louisville for the Kentucky Derby, your outfit should be part of the spectacle. Race day tailgating is steeped in tradition, drawing major inspiration from equestrian elegance—think classic details, bold accessories, and of course, standout hats. For the ladies, channel your inner Kate Middleton with a tailored green tweed jacket, slim trousers tucked into riding boots, and a crisp white blouse for a look that’s chic yet grounded in the heritage of the sport. As the temperatures rise, swap heavier fabrics for sundresses or A-line skirts in preppy prints or pastel hues. Gentlemen, this is your chance to elevate everyday pieces—a collared shirt under a tweed blazer, khaki pants, and a quilted vest can go a long way. And don’t forget your hat: it’s the crown jewel of race day attire, a stylish tradition that ties the whole look together while shielding you from the sun. From southern sophistication to equestrian flair, dressing for the races is all about celebrating timeless style with a spirited, festive twist.

Learn more here: https://wineandcountrylife.com/what-to-wear-to-the-steeplechase/

Option 4: Derby Day at Gertie’s Bar – A Kentucky Derby Celebration in Nashville
May 3, 2025 | 4:00 PM

Step into the spirit of Churchill Downs without leaving Nashville at Gertie’s Bar at The 404 Kitchen for a one-of-a-kind Kentucky Derby party, presented in partnership with Woodford Reserve. Starting at 4 PM, guests are invited to don their best Derby attire, walk the red carpet, and enjoy an immersive experience filled with mint juleps, southern hors d’oeuvres, and the most exciting two minutes in sports.

Infield Pass holders ($35) will enjoy classic Derby cocktails, bites from Chef Matt Bolus, access to a themed photo booth, and entry into a raffle featuring special Woodford Reserve prizes.

For a more elevated experience, opt for the Millionaire’s Row Pass ($125), which includes everything from the Infield Pass plus exclusive access to the rooftop patio and loft, an open bar, a mint julep fountain, cigar rolling, and a 4-course dinner paired with select wines and cocktails after the race. Whether you’re in the infield or on Millionaire’s Row, this is Nashville’s ultimate Derby Day destination.

Learn more here: https://www.the404nashville.com/