About 200 carolers had just begun the second verse of the classic Christmas song “The Friendly Beasts” when a little girl let out a squeal of delight. About 20 feet below the balcony, on the floor of the large domed barn, two of the half-dozen dairy cows were butting heads. As the grazing heifers lifted their horns, their playful roughhousing seemed like a display of holiday cheer.

On Saturday, the Churchtown Dairy in Claverack, N.Y., once again hosted a Yuletide tradition: caroling to the herd of 28 cattle that call the cathedral-like barn their winter home. What began a decade ago as a way for the farm’s staff and their families to celebrate the herd has since grown to an annual tradition that brings locals and out-of-towners to the farm’s 250-acre property each December.

This year, preregistration for the two caroling events filled up within hours of going online. Farm staff fielded phone calls from frustrated would-be carolers, some of whom blamed an Instagram post advertising the event for its rise in popularity.

“We’re considering adding a third night next year to accommodate all the interest,” said Grace Pullin, Churchtown’s director of partnerships and programs.

There were more than a few repeat carolers at Saturday’s event. Ashlyn St. Ours, 33, who attended her first caroling last year, called it a “beloved tradition.” This year, it even got a shout-out in her annual Christmas letter.

Another attendee, Sharon Mclees, 64, has attended for six years. Growing up around cows, Ms. Mclees said she felt comforted by the tranquillity at Churchtown. “I love the farm atmosphere,” she said. “It’s just so back to nature.”

Churchtown Dairy was founded in 2012 by Abby Aldrich Rockefeller, the granddaughter of the business magnate John D. Rockefeller, but the property has been under her family’s purview for decades. Her mother, Peggy Rockefeller, purchased the land as part of a larger acquisition of over 2,700 acres by the American Farmland Trust, an agricultural nonprofit Peggy started in 1980.