A Holiday Season Straight Out of a Hallmark Movie in Downtown Baraboo

There’s something undeniably magical about the holiday season in Downtown Baraboo. As soon as Thanksgiving wraps, our charming little town transforms into a scene that feels lifted straight from a Hallmark movie twinkling lights draped across the Courthouse Square, storefront windows glowing with festive displays, and that warm, small-town spirit you can’t quite describe… but you can absolutely feel.

With more than 40 locally owned shops, Downtown Baraboo is truly the heart of holiday shopping. From curated boutiques and handmade goods to home décor, gifts, cozy winter fashion, and stocking stuffers galore, the streets are lined with small businesses ready to help you find something special. When you choose to support these shops, you're not just buying a gift you’re supporting a dream, a family, and a community that thrives because of you.

And the best part?
Your favorite stores are open seven days a week from now until Christmas, making it easier than ever to shop small, explore local, and enjoy everything our downtown has to offer.

Weekend Magic: Horse-Drawn Wagon Rides + Santa Visits

Every Saturday from 11 AM to 2 PM, the holiday spirit comes to life with horse-drawn wagon rides around the Square one of Downtown Baraboo’s most beloved traditions. It’s the perfect way to slow down, take in the sights, and soak up that nostalgic winter charm.

Even more magical?
Visits with Santa at the historic Al. Ringling Theatre, where your little ones can share their Christmas wishes with Santa C.—Baraboo’s very own hometown Santa. The theatre transforms into a festive wonderland, giving you all the cozy Gilmore-Girls-in-Stars-Hollow vibes.

Why Downtown Baraboo Feels Like a Holiday Movie Set

There’s a certain magic here that no big-box store or mall can recreate:

•  Glittering lights illuminating century-old buildings
• Snow falling softly over the Square
• Local cafés serving warm drinks as shoppers stroll by
• Friendly faces that know your name
• Hidden gems inside every boutique

It’s the kind of place where memories are made. Where holiday traditions feel timeless. Where community matters. And where supporting small businesses truly makes a difference.

So grab a peppermint mocha, bundle up in your coziest scarf, and come experience the charm of the season in Downtown Baraboo. Whether you're shopping for gifts, taking the kids to see Santa, enjoying the wagon rides, or simply soaking in the holiday atmosphere, your presence brings this town to life.

This year, shop local. Shop small. Shop Baraboo.
The spirit of the season is here and you’re part of what makes it shine.