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The individual cookies will be quite crisp when cooled. Fill them a day or two before you want to eat them and place in an airtight container. The filled cookie will soften up "just enough".
This is a very old recipe, and one of my favorites, and, yes, my Grandma Kirk really did make these cookies every year. One of these cookies is hearty enough for a quick breakfast on the run. If you are serving them for dessert you may want to us a smaller round cutter. ~Jan~