Jumping Into Steeplechase

Spring has arrived in the Brandywine Valley, and that can only mean one thing — steeplechase season is here! With the season’s return comes the highly anticipated lineup of three dazzling May weekend races we’ve eagerly awaited since the bleak days of winter. And, to continue the equestrian excitement, the Devon Horse Show takes place from May 21 through June 2.

These exciting races are a perfect excuse to spend the weekends in the countryside. Breathe in the fresh air and enjoy displays of equine athleticism alongside glamorous fashion and the best tailgating with all the essentials — delicious food, intoxicating drinks, and sparkling crystal and silver — all while supporting the great causes the racing season benefits.

Steeplechase races continue to be equal parts tailgate party, fashion show and sporting event, allowing fans to join the tradition and enjoy a day in the country. For everyone from experts to first-timers, we’ll guide you through what you need to know about this year’s races to make memories you won’t forget.

Chasing Victory and Style

First, what exactly is a steeplechase? It’s time for our annual refresher! Steeplechase races date to 18th-century Ireland, where riders tested their horses’ athleticism by racing across rolling hills and jumping over the iconic stone walls and wooden fences that dotted the landscape. Races would typically have a starting point, like a church steeple, and end at another landmark — hence the name steeplechase. The main difference in our three events is that a steeplechase is sanctioned by the National Steeplechase Association, while a point-to-point race is not.

While the horses race toward victory, you’ll notice many spectators are also competing for a title. The honor of Best Dressed is a longstanding tradition at all three races, where prizes and bragging rights go hand in hand. This love for fashion dates back to 18th-century Europe, which set the standard for the styles we see today.

The tradition of women wearing stylish hats to the races began in 1711 at Royal Ascot, a flat race attended by British royalty and governed by strict dress codes including for elaborate hats, a symbol of wealth, status and femininity. This aspect of race-day pageantry crossed the Atlantic, landing at several early American equestrian events, including the first Kentucky Derby (1875), the Virginia Gold Cup (1922) and Iroquois Steeplechase (1941) in Nashville, continuing the tradition of race-day hats.

Today in the Brandywine Valley, steeplechase crowds figuratively tip their hats to this stylish tradition. Fashionable ladies in whimsical fascinators or wide-brimmed hats, adorned with a kaleidoscope of vibrant flowers, feathers and other decorations, blend nostalgia and pageantry with a personal twist. Men can join the fun with tweed jackets, bold ties and pocket squares, and the occasional classic Panama straw hat.

And our best advice for winning Best Dressed? Start with the hat and let the rest of your outfit follow that lead. You’ll make a bold statement without saying a word.

Chasing the Triple Crown: The Quest for Glory!

We can’t talk about horse racing without mentioning the legendary Triple Crown Races, a prestigious series of flat races for 3-year-old thoroughbreds, testing speed, stamina and recovery, and which only 13 horses have won in the past 100 years.

• The Kentucky Derby (1.25 miles, May 3, Churchill Downs, KY). The first jewel in the crown is the Run for the Roses (winner gets a blanket of roses) and “The Most Exciting Two Minutes in Sports.” It’s known for celebrity spotting, a sea of colorful hats and its mint juleps.
• The Preakness Stakes (1.1875 miles, May 17, Pimlico, MD). While the Derby has glamour, this short race has increased excitement as it determines a potential contender for the Triple Crown, not won since Justify in 2018.
• The Belmont Stakes (1.5 miles, June 7, Belmont Park, NY). The oldest of the races, named the “Test of the Champion” because of its grueling distance, the Belmont is known for dramatic victories, especially when the Triple Crown is on the line.

47th Winterthur Point-to-Point

On the first Sunday in May, the elegant crowd on the thousand-acre former du Pont country estate eagerly awaits the four thrilling steeplechase races of the annual Winterthur Point-to-Point. Soon, the horses will thunder over the three-and-one-quarter-mile course, jumping eight timber fences a total of 17 times. Since its beginnings in 1979, Winterthur continues its tradition of prestige horse racing.

While the steeplechase races are the mane event — featuring professional and amateur riders vying for purses totaling $60,000 — race day also offers festivities for the whole family, including your four-legged companions. Cheer on the pony races, enjoy the Parade of River Hills Foxhounds, marvel at the George A. “Frolic” Weymouth Antique Carriage Parade and admire the display of vintage Rolls-Royces and Bentleys. Add to the fun at the Winterthur Hunt area for stick-horse races, pony rides and hayrides.

For the stylish set, dress to the nines and let your fashion sense shine! The chicest chapeaux will compete to win a fashionable hat or fascinator from Christine A. Moore Millinery or $250 gift cards. Stroll through the Marketplace to discover more stylish apparel, equine-themed gifts plus tastes from local food purveyors. Visit the WDSD 94.7 FM tent to win passes to the Barefoot Country Music Festival, while designated drivers unwind at the Betty Buzz Lounge with refreshing faux mint juleps or mojitos.

And it’s not a steeplechase without the tailgates — from casual to elegant. So bring your finest tableware and refreshments and compete for the Point-to-Point Silver Tray. Or have a relaxing day and reserve a spot in a catered tent, ranging from the Winterthur Hunt Brunch Tent (21 and up) to the family-friendly Fiesta Tent, all within sight of the finish line. While you watch, build your stable of horses from the day’s races and place your wagers using StableDuel.

Proceeds from this fundraising event support Winterthur’s environmental and landscape stewardship initiatives, such as programs managing woodland, meadow and wetland habitats and preserving the gardens.

So, grab your finest hat and pack your tailgate for a day guaranteed to please.

IF YOU GO: Sunday, May 4. 5105 Kennett Pk., Winterthur, DE. Admissions: $60–$300, advance sales only. Rain or shine. 800-448- 3883. Winterthur.org.

TIP: Bring your wristband back during the month of May for a day’s free admission to Winterthur.

32nd Willowdale Steeplechase

Hold the reins, because the spring equestrian season has more fun in store. The Willowdale Steeplechase continues “Racing for Life” on May 10 on the beautiful 160-acre property nestled in picturesque southern Chester County. Celebrated over Mother’s Day weekend, this annual event combines tradition, community spirit and equestrian excellence.

Willowdale features six officially sanctioned jump races across three beautifully designed courses of rolling turf. Spanning just over 1.2 miles, the courses boast impressive elements. The hurdle races will run over natural hedges, while the timber course features solid post-and-rail timber fences, hedges, an open ditch plus the iconic Willowdale Water Jump, which includes an 18-inch drop and a 12-foot span. The courses are set in a natural amphitheater, offering excellent visibility and thrilling vantage points for spectators to enjoy the action. Riders will race for purses totaling $115,000.

Race-day activities also include the lovable Jack Russell Terrier Races and the fan-favorite Pony Races. Car enthusiasts can explore the Classic Car Exhibit, featuring vintage vehicles, or register to participate with their own pre-1985 ride. Additional attractions include a vendor market with souvenirs, boutique clothing and jewelry, plus local food and sweet treats. Youngsters can join the fun in the Kids’ Alley, which offers stick-pony jumping courses and coloring contests.

Join fashionable spectators and take part in the Tailgating Contest, with this year’s theme, “The Wicked Wild West at Willowdale.” Display your finest attire — best dressed and best hats — and tailgate spreads to show the judges how you Defy Gravity! New for 2025, the Turf Club offers an exclusive, fully catered tent with prime racecourse views and TVs to follow the action in comfort. Plus Malvern’s Pennsylvania Distilling Company is developing signature cocktails for the races.

Willowdale’s mission goes beyond equestrian competition — it’s about racing with a higher purpose. The event benefits Stroud Water Research Center and Penn Vet’s New Bolton Center, both dedicated to advancing the stewardship of our natural resources and educating the next generations.

IF YOU GO: Saturday, May 10. 101 E. Street Rd., Kennett Square. Rain or shine. Advance sales only. 610-444-1582. WillowdaleSteeplechase.org.

TIP: Visit the paddock area to get a close-up view of the horses and jockeys preparing for their races.

94th Radnor Hunt Races

Photos by Bob Plant

The grand finale of our region’s three-event steeplechase series, the Radnor Hunt Races celebrates nearly 100 years on the Main Line on May 17 at the W. Burling Cocks Racecourse at the Radnor Hunt Club grounds. This historic event continues the springtime tradition of elegance, excitement and fun with a day capped by four thrilling races and memorable experiences with friends and family.

All four jump races are sanctioned by the National Steeplechase Association and feature some of the best thoroughbreds, riders and trainers in the county. Racegoers will see a variety of events, as each race differs in length and challenges, such as the type of track and the number of jumps.

Other special events planned around the races include the fifth annual Katherine W. Illoway Invitational Sidesaddle Race, the return of the adorable pony races, the perennial antique carriage parade and the beloved parade of foxhounds. While roaming the grounds, take time to people-watch, as patrons don fabulous hats, jaunty bow ties, and colorful outfits of all styles.

The Picnic Tailgating competition theme this year is “Old Hollywood Glamour.” Think vintage movie posters and the golden age of cinema or channel your inner Marilyn Monroe or Cary Grant to wow the judges and earn bragging rights.

Box seats on the hillside are at the center of the action and the most traditional way to watch the races, but there are plenty of options to enjoy the day. Tailgating on the rail or in a rail tent gives your party a perfect spot for up-close viewing. For a hassle-free VIP experience, try Skip’s Fox’s Den — featuring gourmet catering, open bar, private restrooms — located on the hillside this year, overlooking the finish line. Children accompanied by an adult are welcome.

The Radnor Hunt Races have been “Racing for Open Space” for more than 40 years and raised over $5.5 million for the Brandywine Conservancy, the races’ sole beneficiary. These funds have fueled the Conservancy’s vital efforts to protect open space and water resources in the Brandywine Valley.

IF YOU GO: Saturday, May 17. 826 Providence Rd., Malvern. Rain or shine. Purchase tickets by May 7. 610-388-8383. RadnorHuntRaces.org.

TIP: Leave the stilettos at home, as the grounds are grassy fields. Flat shoes recommended.

View each race’s schedule of events here.