Caroline Winterstein of Queen Anne’s County was crowned the 64th Maryland Dairy Princess on Sept. 4 during the annual contest at the Cow Palace at the Maryland State Fairgrounds in Timonium, edging out two other regional finalists for the title.
Winterstein, who represented the Eastern Shore region, will spend the coming year serving as the state’s official ambassador for Maryland’s dairy farmers, making appearances at fairs, schools, grocery stores, and other events to promote milk and dairy products — an obligation the association considers Maryland’s official beverage. She also won the competition’s Best Presentation Award over the three-day event.
Scarlett Heffner of Baltimore County, representing the Upper Chesapeake region, was named First Alternate and won the Best Milk Toast honor. Mikayla Derr of Carroll County was named Second Alternate. “Maryland’s dairy industry is lucky to have this dynamic team to promote their product and way of life,” said Susan Summers, president of the Maryland Dairy Princess Association, calling the winners “trained, professional spokespersons.”
Winterstein splits her time working at Winterstein Farms and Sugar Doodle’s Sweet Shop Ice Cream Parlor, and has served as president of the Sudlersville Super Stars 4-H Club. She was a Maryland General Assembly Page this past spring and a youth tour delegate for Choptank Electric Cooperative. A graduate of Queen Anne’s County High School, she’s now a freshman at the University of Maryland, College Park, studying agricultural and resource economics. She’s the daughter of Will and Beth Winterstein of Sudlersville.
Heffner, the new First Alternate, has served as Maryland FFA State Secretary and Baltimore County Farm Bureau Ambassador, and will receive the American FFA Degree this fall. She plans to study political science at Notre Dame of Maryland University. Derr, an accomplished dairy cattle fitter and judge, is a junior at Francis Scott Key High School and president of the Carroll County 4-H Dairy Club; she also fosters animals for the Humane Society of Carroll County.
The contest also recognized outgoing 2025-26 state princess Leah Spurrier, who received the association’s top Incentive Award for logging more than 100 appearances during her reign, before crowning her successor. Judges for this year’s contest were Robert Fogle of Raleigh, N.C.; Brittany Snyder of Mohrsville, Pa.; and Tony Rice of Arlington, Va.
More information on the Maryland Dairy Princess program is available by contacting Deb Spurrier at mddairyprincess@gmail.com.
