A magical holiday experience in Baraboo
Escape the frenzied crowds and enjoy a magical holiday shopping experience this Christmas in Baraboo.
Every Saturday during the holiday season you can visit Santa Claus, listen to strolling carolers and take a horse-drawn wagon ride around the Rockwellian downtown square from 11-2. Be sure to check out Downtown Baraboo‘s eclectic array of specialty shops delivering distinctive gifts.
Holiday events abound, starting with a new one for 2026: Downtown Baraboo, Inc. will flip the switch on its holiday light installation Friday, November 6. Light Up the Square begins at 5 p.m., kicking off a light display that will run through Dec. 31. This will coincide with Downtown Baraboo’s Sip the Square campaign.
The downtown streets also will host a Community Christmas Market on the afternoon of November 21, culminating in the Christmas Light Parade at 6 p.m.
In nearby North Freedom, it’ll be full steam ahead for the Santa Express at Mid-Continent Railway Museum, with the big guy taking part in scenic rides through the countryside November 28-29 and December 5, 6 & 12.
Here’s an event for those seeking unique gifts crafted by local artisans: Be sure to visit the Very Merry Holiday Fair on December 11 and 12 at Baraboo Arts Center.
The Drifters will stoke your holiday spirit with a Christmas show December 20 at the Al. Ringling Theatre. This historic venue also will present a screening of “Miracle on 34th Street” two days earlier.
Not all of Baraboo’s holiday delights are scheduled. Stop in anytime to try out the latest toys at Just Imagine downtown. Looking for unique gifts the loved ones on your list couldn’t possibly get from anyone else? Check out the fair-trade decor and jewelry at A Sense of Adventure. Hosting Christmas and looking for fresh holiday decor? Be sure to stop at Countryside Refind.
If all that shopping leaves you parched, stop for a beverage at Gina Jenny’s, Driftless Glen Distillery or Al. Ringling Brewing. It’s all part of the charm of an old-fashioned holiday experience in Baraboo.
Great gifts await beyond the downtown square: Just north of town you’ll find Baraboo Candy Company, which sells its signature Cow Pies and other sweet treats at the factory store.
If national brands are what you’re after, the Baraboo Area has you covered. Walmart has toys for kids of all ages, of course, and Farm & Fleet has plenty in store for the do-it-yourselfers on your shopping list.
Unique treasures, heart-warming holiday traditions and entertaining events: It’s all part of the magic of Christmas in the Baraboo Area. Find it all at baraboo.com.
