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An Inside Look at the History of the Races in and Around Delaware

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Photo by Jim Graham

For more than 40 years, Delaware has celebrated its own version of the Kentucky Derby each May. Here’s a look at the beginnings of this beloved tradition.

Point-to-Point at Winterthur

In 1978, Greta “Greets” Layton, a Winterthur trustee, wanted to make the community more aware of the museum and garden. When fellow trustee Julian Boyd suggested a steeplechase race, Layton saw it as a perfect fit.

The first race was held on May 6, 1979. It was a small, casual affair with no cash prizes, only silver trophies modeled after early American silver in the Winterthur collection. Today, Point-to-Point at Winterthur is known for its grand tailgate picnics, high-stepping carriage horses and stylish Rolls-Royces.

When the Delaware Legislature passed a law in 2006 that allowed Winterthur to offer cash purses, Point-to-Point became sanctioned by the National Steeplechase Association. Today, the course is a challenging 1.5-mile figure-eight run twice over 17 timber fences. Races include the Isabella du Pont Sharp Memorial ($20,000 purse), the Winterthur Bowl ($25,000 purse), the Vicmead Plate in Honor of Louis “Paddy” Neilson III ($15,000 purse) and the Middletown Cup.

Located on beautiful Kennett Pike outside Wilmington, Del., Winterthur Museum, Garden & Library encompasses more than 900 acres of quintessential Brandywine Valley landscape, 70 acres of world-class gardens and a stunning mansion featuring the most significant collection of American decorative arts in the world. From the mid-18th century to the mid-19th century, Winterthur was home to three generations of the du Pont family.

The museum was founded by collector and horticulturalist Henry Francis du Pont on the estate that had been his home since childhood. His 175-room house features furniture, home accessories and works of art made or used in America from 1640 to 1860.

The gardens at Winterthur. Photo by Jeannette Lindvig.

With harmonious color and successive blooms year-round, the 70-acre Winterthur Garden was designed by Henry Francis du Pont and is one of the oldest continually operating naturalistic gardens in North America. It’s also a resource for scholars, landscape architects and horticulturists.

Winterthur Library provides staff, students and the general public with research materials about American decorative arts. It’s open to the public free of charge. In partnership with the University of Delaware, Winterthur also offers two graduate programs focused on the study of art conservation and American material culture.

Winterthur also hosts films, musical performances, lectures for scholars and the general public, and study programs on decorative arts. Among its popular family programs are annual events like June’s Enchanted Summer Day and October’s Truck and Tractor Day. Winterthur also hosts the Delaware Antiques Show, a top-ranked weekend-long fall event. A beloved Brandywine Valley tradition, Yuletide at Winterthur tours depict American holiday celebrations of the past, along with the holiday rituals of the du Ponts.

Visitors are always free to explore the estate. All outdoor areas are available to members year-round. The retail store offers books, clothing accessories, decorative items for home and garden, children’s gifts, and more.

Winterthur’s largest single-day fundraiser, Point-to-Point supports maintenance and preservation of the gardens and estate. The annual event was spearheaded in 1978 by Greta “Greets” Layton, who grew up around horses and steeplechasing. Drawing on the knowledge of Russell B. Jones Jr., Louis “Paddy” Neilson III and other local horsemen, Layton launched the organizational effort. The first weekend in May seemed an ideal time for the race, as it didn’t conflict with the Radnor Hunt Races and other area equestrian events that already featured prominently in sporting and social calendars. It also rounded out a series of race meets hosted by the Delaware Valley Point to Point Association.

For the first Point-to-Point in 1979, spectators were mainly hardcore enthusiasts of the sport. They dressed in country clothes and sat on blankets, or they stood on hillsides to watch the action. More than 1,000 people attended the event—a far cry from the 16,000 the event draws today.

In the early years, winners of the five races were awarded trophies modeled after notable pieces of silver in the Winterthur collection. Races were named after people and organizations familiar to Winterthur supporters and area residents: the Isabella du Pont Sharp Memorial, the Vicmead Plate, the Middletown Cup, the Winterthur Bowl, the Crowninshield Plate, and the Greta Brown Layton. The latter, a trophy in honor of Greets Layton, was awarded to the owner, trainer or rider who accumulated the most points.

A historic change in the event occurred in 2006, when the Delaware Legislature passed a law allowing Winterthur to pay purse monies to winning owners. Now sanctioned by the National Steeplechase Association, Point-to-Point is the second professional sporting event in Delaware— and it’s now a highly anticipated event. For many, it signals the start of spring and summer outdoor activities. Several generations of families have helped organize Point-to-Point, and they also compete in the races. Preparations take place year-round and involve all departments at Winterthur. The course is fertilized and mowed; jumps are maintained; hedges and border plants are trimmed.

The event is a celebration of Winterthur’s long history as a farm and country destination. For generations, much of the racecourse served as pastureland—first for sheep, then for dairy cows. Today, motorists enjoy sweeping views of the meadows and the racecourse throughout the year. In May, it all undergoes a transformation for one of the Delaware Valley’s premier sporting events, drawing families from around the region.

Photo by Jim Graham

Radnor Hunt Races

Celebrating 91 years in May, the Radnor Hunt Races are a time-honored tradition in Chester County, Pa. With roots that go back over 250 years to Ireland and England, steeplechase has a rich history and tradition in the Mid-Atlantic. The beautiful pastoral landscapes that make up this region mimic the ideal conditions of the sport’s origins abroad, while also reflecting land-conservation efforts.

As one of the oldest regional steeplechases, the event is an annual rite of spring that dates back to 1930. That tradition continues in 2022 on the third Saturday in May, with professional jockeys and thoroughbred horses competing in five jump races for their chance at valuable purses.

The Radnor Hunt Races will follow all CDC and Pennsylvania Department of Health guidance on COVID-19. The event is held rain or shine, so there are no refunds offered.

The Radnor Hunt Races and many of the annual steeplechase events that take place in southeastern Pennsylvania and northern Delaware are held on land permanently protected by the Brandywine Conservancy and its partners. The legacy of protecting open space has allowed the sport of steeplechase racing to flourish in this region. More than 30 percent of Chester County alone is protected open space—totaling over 140,000 acres.

While the connection between open space preservation and steeplechase racing has always been part of Radnor Hunt’s heritage, it wasn’t until the fundraising partnership with the Brandywine Conservancy began that the event became associated with “Racing for Open Space.” The two joined forces over 40 years ago in a partnership spearheaded by the late Mrs. J. Maxwell “Betty” Moran and the Conservancy’s late cofounder, George A. “Frolic” Weymouth, that has since raised over $5 million.

Delaware races

Brandywine Conservancy’s Laurels Preserve. Photo by C. Bowers.

The Brandywine Conservancy is a leader in protecting water and preserving the breathtaking landscapes, rich history and active farmland in southeastern Pennsylvania and northern Delaware. Since 1967, the organization has protected over 69,000 acres of open space, including the Radnor Hunt racecourse itself and surrounding lands. It continues to improve and safeguard water quality, land protection, outdoor recreation and historic preservation throughout the region. It works closely with private landowners who wish to see their lands protected forever, and it also provides innovative land use and environmental planning services to municipalities and other governmental agencies.

Willowdale Steeplechase

The excitement continues with the 29th running of the Willowdale Steeplechase on Saturday, May 14. This much-loved Chester County tradition resumes at full spectator capacity this year with six exciting steeplechase races.

What began as a vision by community leader W.B. Dixon Stroud Jr. is now a premier racing event and a perfect day of fun activities for the entire family. The first Willowdale Steeplechase came about when Dixon—who’d competed at the highest levels in steeplechase and polo competition—decided it was time to have a top-notch steeplechase event in the heart of Chester County’s Cheshire Hunt Country. Combining his love for the sport and his commitment to the community, Stroud enlisted the help of many others for the inaugural running of the Willowdale Steeplechase in 1993. Since then, the event has raised over $1 million for local charities.

Willowdale features a world-class steeplechase course in a community known for its top jockeys, trainers and owners. For the 29th running, Willowdale welcomes back the Pony Races, Jack Russell Terrier Races, boutique shopping, food vendors and the fun and educational Kids’ Alley. Family and friends can pack their picnics, put on their best hats and race outfits and enjoy the fun of the tailgate, hat and best-dressed competitions.

In response to the pandemic, Willowdale will follow all state and local COVID-19 guidelines while returning to its traditional spectator model—with the addition of a limited number of last year’s Private Party Paddocks. Available on a first-come, first-served basis, this exclusive tailgating opportunity includes parking for one car, a 10-by-10-foot tent, a table and admission for up to 10. Each area will be designated at 12 feet from neighboring paddocks. This year, Willowdale is also introducing something new: the elegant Jockey Club at Willowdale, where tables are available for purchase.

From general admission to tailgate parking to Private Party Paddocks, your options are many.

As a 501(c)(3) nonprofit organization Willowdale Steeplechase raises funds for clean water and veterinary excellence through donations to the Stroud Water Research Center and the University of Pennsylvania School of Veterinary Medicine’s New Bolton Center.

Related: Jack Russell Terrier Races Are an Adorable Steeplechase Prelude

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