Former West Point Thoroughbreds campaigner Chestertown has been named the recipient of the Down Broadway Award as New York’s Retired Racehorse of the Year, presented during New York Thoroughbred Aftercare Day at Saratoga Race Course.

The annual award recognizes a retired Thoroughbred that has successfully transitioned to a meaningful second career after racing, and Chestertown is a deserving recipient.

A son of Tapit out of Grade 1 winner Artemis Agrotera, Chestertown raced for West Point Thoroughbreds, Robert Masiello, the Broman family, Woodford Racing and Siena Farm. Trained by Hall of Famer Steve Asmussen, he won five races and earned more than $428,000, highlighted by his victory in the Albany Stakes at Saratoga.

Today, Chestertown is a familiar face around Saratoga as the pony horse for NYRA Head Outrider Miguel Gutierrez. His calm temperament and professionalism have made him a perfect fit for his new role, earning admiration from horsemen and fans alike.

Chestertown’s story is a reminder that a successful racing career can be just the beginning. Seeing former West Point runners thrive after they leave the track is something we care deeply about, and it’s one of the reasons we established the Congie Black & Gold Fund—to help ensure our horses have the opportunity for fulfilling lives after racing.

Congratulations to Chestertown, Miguel Gutierrez, and everyone who helped make this well-deserved recognition possible. We’re proud to see Chestertown continuing to make an impact at Saratoga, just in a different role.