10 favorite recipes from 20 years of the Star Tribune Holiday Cookie Contest

In the 20 years we've held the Star Tribune Holiday Cookie Contest, we've published 102 recipes — 20 winners and 82 finalists — submitted by readers from all over Minnesota. The goal of the contest has always been to provide our readers with compelling new recipes, and we're grateful for the endless creativity and enthusiasm.

Each year, I prepared the winning and finalist recipes, several times, carefully testing them to ensure that the measurements and instructions were correct.

For some of those recipes, that was the only time I ever baked them. We all have our preferences, right? But many were quickly incorporated into my baking rotation, not just during the holiday season but year-round.

On the occasion of the contest's 20th anniversary, I wondered, "Which recipes have I turned to, over and over, through the years?"

That's a Minnesota Nice way of asking, "Which ones are my favorites?" The answer became this Top 10 list, which is organized in alphabetical order, because there's no way I can rank them any further than that.

This year's Star Tribune Holiday Cookie Contest is my last. When we staged that first competition in 2003, we had no idea that it would become an annual event, a cookbook or that it would develop into a December tradition for many cookie-loving Minnesotans. It certainly became a cherished part of my holiday routine.

Almond Palmiers

In hindsight, this finalist probably should have won the 2011 contest. That's not to say that the winning entry, Swedish Almond Chocolate Macaroons, wasn't worthy, because everything about that hugely appealing recipe screams "blue ribbon." So, a tie?

It's entirely my fault that this exceptional cookie didn't advance to the winner's circle. After climbing up on a high horse about the importance of baking from scratch, I argued that, because the recipe's primary ingredient is commercially prepared puff pastry, the cookie didn't qualify for the top prize.

Lesson learned, and that humbling experience came in handy when additional less-than-traditional components (Kellogg's-brand Club crackers, for example, in the popular Kit Kat Christmas Bars) continued to trickle into the contest's inbox. (Baker's tip: I highly recommend using the all-butter Dufour brand puff pastry for this recipe; find it in the frozen foods section of Whole Foods Market and most natural foods co-ops.)

Beyond their exceptional flavor, these delicate, elegant beauties also radiate an "I fussed" vibe, yet the slice-and-bake formula is the opposite of complicated and time-consuming.

Kay Lieberherr of St. Paul based her recipe on the almond palmiers she was forever buying at Surdyk's Cheese Shop in Minneapolis. I understood her obsession, because, for years, that decadent, flaky treat was also a favorite of mine. They were introduced to me by my late colleague Kristin Tillotson, who was crazy about them and would often leave them at my desk as a thoughtful pick-me-up. Sadly, Surdyk's no longer sells them, but, thanks to Lieberherr's craftsmanship, you can bake her version. Find the recipe here.

Almond Triangles

That these temptations are delicious comes as no surprise; after all, the ingredients include four sticks of butter and five-plus cups of sliced almonds, a can't-miss combination.

When Charlotte Midthun of Granite Falls, Minn., submitted this recipe in 2009, it wasn't the first bar cookie to appear in the contest (that path was paved by a 2005 finalist, Cardamom Shortbread Cookies). When it won, we received disapproving commentary along the lines of, "A bar is not a cookie." We respectfully disagree.

All those sliced almonds don't come cheap, and in the story we noted that an economical source was We Are Nuts in St. Paul, where the bulk price was significantly less than the average supermarket price.

Two days after the recipe was published in Taste, I followed my own advice and headed to We Are Nuts for sliced almonds. That's when I witnessed, firsthand, the level of enthusiasm for our cookie contest. The store was crowded, and after a bit of browsing, I joined a long line at the checkout counter. All of my fellow shoppers were also buying 1-pound bags of sliced almonds.

When it was my turn to pay, the very nice man on checkout duty repeated the same comment that he gave to every previous customer: He had a wonderful recipe for sliced almonds, and then handed me a photocopy of my story. I was so tickled that I sheepishly told him that I was the author. Before I could say another word, he blurted out his thanks, saying, "We're going to be able to send our kid to college on the sale of all of these sliced almonds."

Find the recipe here.

Cardamom Cookies

Matt Boisen of Owatonna, Minn., created this fragrant, chewy cookie after a trip to Denmark, where he seemingly encountered cardamom everywhere. That was his memory, anyway.

"I know a lot of people run away from cardamom, but to me, it's intoxicating," he said.

I have the same reaction. What's great about this recipe is that the cookies themselves are a basic lunchbox sugar cookie formula, which means they come together in a snap. It's the cardamom — and the icing – that contribute holiday pizazz. Find the recipe here.

Cranberry Cornmeal Shortbread Cookies

In the 15th year of our contest, Mary Martin of Minneapolis seemed to sense that our collective taste buds were headed in a less-is-more direction. At least when the subject was "sweet."

While these festive treats firmly land in the cookie realm, the inclusion of rosemary, cayenne pepper and yellow cornmeal means that they also flirt with the savory side of the baked-goods continuum. That inventiveness earned Martin our top prize in 2017, but it was Star Tribune readers who really won, because these easy-to-prepare cookies (no electric mixer required) taste as good as they look. Better, even. Find the recipe here.

Cranberry Pecan Swirls

"This is the first one I'd grab from the cookie tray" was the universal reaction when this colorful, spiraled beauty came up for discussion among the judges at our 2012 semifinalist taste-a-thon, underscoring how we all eat with our eyes.

But this no-fuss slice-and-bake formula, a finalist in that year's competition, isn't just about good looks, thanks to the lively combination of pecans, orange zest and fresh cranberries.

"I'm always on the lookout for anything cranberry," said baker Annette Poole of Prior Lake. "If there's a cranberry recipe, I've got to have it."

Find the recipe here.

Devil's Delight Cookies

A sure way to reign supreme in our contest has been to place chocolate at the forefront, and the numbers bear this out: Nine out of our 20 winners have been chocolate-centric. Our judges clearly have a hankering for chocolate; then again, so do our readers.

Choosing just one favorite chocolate recipe out of all of those fabulous winners is no easy task, but if the sole criterion is "Number of Times I've Baked Them Over the Years," then this intensely chocolaty cookie — which also features a subtle nudge of heat — takes the prize, with Orange-Chocolate Cookies (see below) coming in a close second.

Michelle Clark of St. Paul devised the 2005 winning recipe after falling for a cinnamon- and chile-infused chocolate truffle at Legacy Chocolates in St. Paul and wondering if she could devise a cookie that would mirror those flavors. She did, and we're forever grateful. Find the recipe here.

Italian Almond Cookies

Because we're in the storytelling business, we love a good story as much as we love a good recipe, and 2014 winner William Teresa of Minneapolis more than delivered on this one-two punch.

He encountered this uncomplicated cookie while studying in Italy. On most weekends, he and the fellow student he was dating would travel to her parents' house, where an espresso ritual included these not-too-sweet cookies. Shortly before returning to Minnesota, he asked his girlfriend's grandmother for the cherished family recipe. She politely declined. A family secret is a family secret.

Back in Minnesota, Teresa spent the next year trying to replicate it. After finally mastering the details, he developed his own ritual of baking them for friends and family, and they encouraged him to enter our contest. He did, and he won. Find the recipe here.

Orange-Chocolate Cookies

There are so many reasons to bake this buttery treat. The orange-chocolate pairing is an off-the-charts delicious combination. They come together fairly quickly, especially for a cutout cookie. Appearance-wise, they are irresistible.

Eileen Troxel of St. Paul came across the recipe in the now-defunct Traditional Home magazine. That it won our 2007 contest sent a message to future contestants: Yes, our judges appreciate original recipes, but a good cookie is a good cookie, no matter the source. Find the recipe here.

Pistachio Orange Cookies

Because December heralds the arrival of citrus season, I've always associated the holidays with the flavor of orange, which explains my love of Orange Chocolate Cookies (see above).

Turns out, orange and pistachio are another enormously appealing pairing. In 2010, baker Scott Rohr of St. Paul took our top prize by dressing up his grandmother's beloved sugar cookie recipe with two favorite flavors: the bright pop of orange and the crunch of pistachios; the latter's seasonally appropriate green only adds to the festivities.

Also, as a lifelong fan of the Oreo, I've always been an advocate for sandwich cookie recipes. Up to that point, we'd seen three in the contest — Alfajores in 2004, Almond Sandwiches in 2007 and the fabulous Clare-oes (more chocolate!) in 2009 — and it was a treat to add another to the pantheon. Find the recipe here.

Spumoni Squares

Another bar cookie, and another example of a Star Tribune reader — six-time contest finalist Joanne Holtmeier of Edina — who found recipe inspiration in favorite non-cookie foods, in this case the spumoni ice cream at Sebastian Joe's Ice Cream Cafe in Minneapolis.

With its cheery dried fruit-and-nut topping and a crave-worthy base (perfumed, of course, with the flavor of almonds), this 2020 winning recipe was a total pandemic brightener. Find the recipe here.

Whiskey Gingers

OK, my math skills are obviously subpar, because this is 11.

But how could I not include these gotta-bake (and gotta-eat) cookies, which epitomize the baking axiom "more is more"? No wonder they won our 2019 contest. Find the recipe here.

And although it's too early to tell, my guess for the 2022 cookie that will land on my most-baked list is finalist Melissa Lundquist's Spiced Orange and Rye Shortbread Cookies. With its Swedish limpa flavor notes, it pretty much lands smack dab in the Food of My People territory.