It wasn't easy to whittle down more than 150 entries into this year's five winning cookies. This year's batch ranges from longtime friends of the Holiday Cookie Contest to bakers who developed a winning recipe right out of the gate. All belong on your cookie tray and are delicious additions to our Cookie Finder. Find these and all the other past winners at startribune.com/cookies.
WINNER
Earl Grey Butter Cookies with Dark Chocolate-Orange Filling

Baker: Catie (Seltz Drew) Fesko of Ham Lake.
The scoop: The famous oval-shaped Pepperidge Farm cookies are a favorite of Fesko's, but she rarely sees them made in home kitchens. "I wanted to develop a grown-up version with influences of my favorite flavors — Earl Grey tea, dark chocolate and orange."
Hold the gluten: Fesko followed a gluten-free diet for eight years, and says this recipe turns out "quite well" if gluten-free flour is used in place of all-purpose flour.
First time's a charm: When she was eating gluten-free, Fesko said she became used to reconfiguring recipes to make them work for her diet. "I just got more and more confident," she said. "But I'll be honest, this is the first time I've ever developed a totally new recipe from scratch and I'm glad it was such a success."
A winning year: "This was just a fun idea I had seen advertised in the Star Tribune — I didn't expect to win," she said. She only made the winning recipe twice before being satisfied with the outcome. "It must be a fluke," she said with a laugh. But her winning ways started earlier this year; her almond cake won a red ribbon at the Minnesota State Fair in the international cake category. She had so much fun with that contest, she decided to give this one a whirl.
Baker's tip: The cookies are crisp and delicious and very Milano-like the first day, but as they sit, the cookies become softer (which isn't a bad thing). "But if you're expecting a nice, crunchy cookie, definitely try to eat them within a day or two." And Fesko's tip for using a toothpick when piping the cookies (see the recipe) is a stellar one.
A chocolate note: Fesko is a fan of dark chocolate, but you can tailor the chocolate to suit your tastes. You'll have extra dark chocolate-orange ganache, but don't let it go to waste: Form it into small truffles, heat it up and spoon it over ice cream or dip a spoonful into a mug of hot chocolate for an elevated cocoa experience.