1. Visit Summers Christmas Tree Farm
For a classic Christmastime experience, look no further than Summers Christmas Tree Farm on the outskirts of Middleton. Family-owned since 1957, traipse the property to discover the perfect tree to take home (complete with that real-deal pine scent you can’t achieve with an artificial tree) and visit their Christmas Shop.
2. Host an “Old Fashioned” Christmas at Craftsman Table & Tap
At Craftsman Table & Tap, you can host a private party that’ll get everyone in the spirit. Called an “Old Fashioned Christmas,” throw a holiday soiree for up to 40, enjoy a curated cocktail menu, relish appetizers, and even take part in a cocktail-making class.
3. Get Festive at Tinseltown
For the holidays, Tanner’s Bar Grill transforms its garage bar space into a pop-up wonderland of dazzling decorations, themed cocktails (like the “Gingerbread Man” and “Frosty Bomb”), and beers on tap. Don’t miss their special events, like an ugly Christmas sweater party and live music.
4. Savor Seasonal Pie at Hubbard Avenue Diner
Hubbard Avenue Diner is a destination for comfort food throughout the year, but during the holidays, it becomes extra cozy, thanks to its amazing seasonal pie offerings. Snuggle up in a booth and delight in flavors like Candy Cane, Egg Nog, Gingerbread, and Pear Apple, a vegan option.
5. Pick Up Gifts at The Regal Find
In downtown Middleton, one must-shop boutique is The Regal Find, which comes alive even more during the holidays. Known for their artisan-made goods and vintage pieces, you can shop here for everyone on your list. Think: one-of-a-kind ceramics, handmade soaps, and Christmas cards you won’t find anywhere else.
6. Gaze at the Waunakee Rotary Lights
On Sunday, November 23, 2025, Waunakee will debut their famous Rotary Lights, located at the Waunakee Village Park. This year, they’re showcasing new displays that add to (over a million!) lights. Grab free candy canes and play your favorite holiday tunes as you drive through all the glittering displays.