SHOREHAM, Vt. — In a wooden barn perched on a grassy hill, some of the most celebrated cows in the dairy business — the bovine royal family of American fancy butter — sampled hay in their new abode.

There's something utterly wholesome about a plate of Pepperidge Farm cookies. The brand, founded by Margaret Rudkin in 1937 and named for her family's pepperidge tree, has long been a staple at ...