The date for Easter changes from year to year, but the Chester County horse racing dates can be depended upon to remain the same each spring.

The 77th running of the Cheshire Races took place Sunday, March 31 at the Plantation Field property near Unionville. There were three pony races and a lead line race for young riders followed by four races over timber fences and a side-saddle race on the flat and three flat races.

The day of racing was dedicated to the late Jonathan Sheppard, who is a member of the Thoroughbred Racing Hall of Fame and the winningest trainer in steeplechasing. He has the most steeplechase wins per year—26 times—during his career, from 1972 to his retirement in 2020.

With the Easter holiday, some of the spectators opted for Easter tailgating complete with spring flowers and tasty Easter treats. Mini Young of Unionville and Jill Hunt of Kennett Square worked together on a tailgate that featured Easter-themed décor and sweets.

“This is what we do, we do it at polo in the summer and at Plantation Field (eventing) in the fall. This is what we do we entertain and try to make it nice for people and have fun,” Young said. “Fox hunting roots are very deep in my family. My mother was a huntsman my step mother was a Master for over 30 years.”

Hunt said,  “My daughter was in Cheshire Pony Club, horses have been part of our life forever.”

Hunt particularly enjoys the social side of the races and seeing friends. 

“It’s a tight-knit horse community,” she said. 

Point to point races like Cheshire grew out of fox hunting, and have a deep connection to the history of Chester County. Some of the spectators came from a great distance to experience the races, like Matt Sweeney, who made the two-and-a-half-hour drive from Long Island. 

“I’m really enjoying it. This is the way racings been run for thousands of years,” he said. “It’s really breathtaking. It’s up close and personal. It’s amazing the access you have here.”

The featured race of the day was the Joseph Walker, III Memorial Cheshire Bowl open timber race for a purse of $20,000. Court Ruler, owned by Leipers Fork Steeplechase was the winner for trainer Leslie Young and rider Freddie Procter.

Proceeds from the day of racing benefit the non-profit Cheeshire Horse and Hounds Foundation, The Cheshire Races are a part of the Delaware Valley Point to Point  Series, which continues on April 7 with the Brandywine Hills Point to Point Races at the Myrick Conservation Center.