Cup of Cheer

The phrase “cup of cheer” is older than nearly every modern Christmas tradition. It appears in English carols and toasting songs as early as the 1700s, when sharing a warm drink was less about the beverage and more about the blessing it carried—an invitation for joy, goodwill, and community to flow from one person to another. Burl Ives helped cement the phrase into Christmas culture with Have a Holly Jolly Christmas, but its spirit has always been the same: lift a cup, lift a heart.

At the heart of the day was our annual hot-chocolate tradition—this year fully reimagined for grown-ups. Instead of international styles or classic cocoa flights, we built the hot chocolate menu around rich, boozy creations: chocolate-stout blends, buttered-rum cocoa, maple-whiskey toddies, and other decadent “after-dark” mugs. Each recipe felt like the warm, indulgent cousin of the hot chocolates we make with the kids with the intent being to drink something warm and for it to warm you up, in more ways than one.

But of course, our day had a lot more to it than just hot chocolate recipes. There mugs and silly crafts and playful games.  It began the moment we pulled out our “Cup of Cheer” mugs—a forest-green one for Miles that he held like a prized treasure Breakfast was intentionally simple but whimsical: coffee from the Advent calendar, freezer pancakes warmed with syrup poured from a miniature mug, and a maple-whiskey mix-in shot served in a mason mug for a wink of grown-up mischief and add just one more layer of cheer. And it also featured the first adult hot chocolate of the day… a chocolate stout beer based hot chocolate.

Midmorning brought Cheerios Christmas Trees, an instant kid favorite. Edison decorated with laser-focus; Miles ate as many M&Ms as he placed. Lunch continued the theme with grilled-cheese bites and tomato soup served shooter-style—because on this day, everything belonged in a cup.

Craft time turned the dining table into a Dollar Tree mug-decorating workshop. Glitter, puffy paint, little foam snowmen, and dripping faux chocolate transformed basic mugs into miniature sculptures. The end products were absolutely adorable and brought smiles to all our faces. And they will be perfect gifts to pass along to teachers and neighbors and family to help brighten their days as well. .

Then came the outdoor chapter: we packed a thermos of hot chocolate buttered rum (complete with a homemade mascarpone compound butter disc to float on top of each pour) and headed to the park. The late-autumn sun stretched long shadows across the playground as the kids clutched warm mugs. Bekah wrapped her hands around hers, smiling over the rim while the sky faded into gold. It was the quietest moment of the whole day—nothing fancy, just warmth meeting cold, winter meeting family.

Evening was our “Cozy & Boozy” tasting, a full mug-themed spread of things that are warm and cheery and comforting, but also jazzed up a bit with that extra element of cheer. There were warm sips of vichyssoise(potato leek soup), champagne bisque shots, parmesan-potato mousse, and scallops with beurre blanc. All came plated in it’s own miniature mug to carry the theme through. Every dish felt like a miniature indulgence—small enough to savor, fun enough to laugh at, fancy enough to feel special.

We toasted with Christmas Cheer champagne flutes before ending the night with the parody film Cup of Cheer, a wonderfully absurd send-up of holiday tropes. Watching it with warm mugs in hand felt exactly right.

By the end of the day, the theme had proven its old promise: a cup isn’t just for holding something warm—it’s for passing something warm along. In every sip, every craft, every park-bench moment, and every shared laugh, the day lived up to its name. We didn’t just drink a cup of cheer; we filled one together.

Activities

• Coffee Advent Calendar

• Cup Of Cheer Trivia

• Dollar Tree Mug Crafts

• Outdoor Play With Thermos Hot Chocolate

• “Cup Of Cheer” Parody Movie

• Cheerful Christmas Magic Playlist

• Snowman Family Mug Set

Menu

• Coffee In Christmas Mugs

• Mini Freezer Pancakes With Warm Syrup

• Maple Whiskey Shooter

• Milk Chocolate Stout Hot Chocolate

• Hot Chocolate Buttered Rum

• Cheerios Christmas Trees

• Tomato Soup Shooters

• Grilled Cheese Bites

• Vichyssoise Potato Leek Soup

• Champagne Bisque

• Potato–Parmesan Mousse

• Scallop In Champagne Beurre Blanc

• Christmas Cheer Champagne Flutes