Discover the Spirit of Christmas
Christmas in Downtown Baraboo
Seven weekends of holiday magic, November 6 – December 23, 2026.
Experience Wisconsin’s best version of a small town holiday. With over 40 locally owned shops, boutiques and restaurants — most open seven days a week until Christmas — Downtown Baraboo is the perfect place to find thoughtful gifts, enjoy festive food and drinks, and soak up the magic of the season.
Each weekend from early November through Christmas offers something special, from markets and parades to family fun and extended shopping hours. Whether you’re planning a girls’ shopping getaway, a family tradition, or simply looking for gifts you won’t find at a big box store, every weekend is a new reason to visit.
This Weekend
September 25–27
Here is what is happening downtown over the next few days.
No events on the calendar this weekend — browse all upcoming events.
Every Saturday, Thanksgiving to Christmas
Santa, and a Free Wagon Ride
From 11:00 AM to 2:00 PM every Saturday, visit Santa inside the Historic Al. Ringling Theatre and take the family on a free horse-drawn wagon ride around the decorated Courthouse Square.
Two traditions that have been part of Christmas in Downtown Baraboo for years — and they cost nothing but the time to enjoy them.
November 6 – December 23, 2026
Seven Weekends of Holiday Magic
Weekend 1
November 6 – 8
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Sip the Square: Holiday Beverage Tour
Experience Sip the Square, Downtown Baraboo’s inaugural season-long holiday beverage tour.
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Light Up the Square
Kick off the holiday season with Light Up the Square, a stunning new courthouse lighting display.
Weekend 2
November 13 – 15
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Holiday Scavenger Hunt
Bring your family on the Downtown Baraboo Holiday Scavenger Hunt!
Weekend 3
November 20 – 22
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Holiday Wine Walk: Santa’s Night Out
Dress as your favorite Santa and join Downtown Baraboo’s Wine Walk.
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Community Christmas Market
Spend the afternoon on Oak Street in Downtown Baraboo browsing handcrafted gifts, artisan goods, seasonal décor, delicious treats,…
Weekend 4
November 27 – 29
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Black Friday & Small Business Saturday
Join us on Black Friday and Small Business Saturday in Downtown Baraboo for holiday deals at local shops,…
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Visits with Santa at the Al Ringling Theatre
Bring the kids to visit Santa inside the Historic Al Ringling Theatre.
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Horse Drawn Wagon Rides Around the Square
Enjoy complimentary horse-drawn wagon rides around the beautifully decorated Courthouse Square in Downtown Baraboo.
Weekend 5
December 4 – 6
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Christmas Passport Kickoff
Pick up a Downtown Baraboo Christmas Shopping Passport, shop at ten participating businesses for $10 each, and redeem…
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Visits with Santa at the Al Ringling Theatre
Bring the kids to visit Santa inside the Historic Al Ringling Theatre.
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Horse Drawn Wagon Rides Around the Square
Enjoy complimentary horse-drawn wagon rides around the beautifully decorated Courthouse Square in Downtown Baraboo.
Weekend 6
December 11 – 13
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Very Merry Holiday Fair
Explore the Very Merry Holiday Fair, shopping items from 40+ talented artisans who are showcasing beautifully crafted, one-of-a-kind…
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Stuff Your Stocking Event
Hunt for the perfect stocking stuffers at participating Downtown Baraboo businesses, spot the festive red stockings throughout downtown,…
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Visits with Santa at the Al Ringling Theatre
Bring the kids to visit Santa inside the Historic Al Ringling Theatre.
-
Horse Drawn Wagon Rides Around the Square
Enjoy complimentary horse-drawn wagon rides around the beautifully decorated Courthouse Square in Downtown Baraboo.
Weekend 7
December 18 – 20
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Experience Christmas in Downtown Baraboo
Join us the last weekend before Christmas to finish up all your Christmas shopping!
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Visits with Santa at the Al Ringling Theatre
Bring the kids to visit Santa inside the Historic Al Ringling Theatre.
-
Horse Drawn Wagon Rides Around the Square
Enjoy complimentary horse-drawn wagon rides around the beautifully decorated Courthouse Square in Downtown Baraboo.
Shop Local, Seven Days a Week
Boutiques, restaurants and galleries on every side of the historic Courthouse Square.
Make Downtown Baraboo Part of Your Holiday Tradition
From the first lighting of the Courthouse Square to the final days before Christmas — markets, wine walks, wagon rides and visits with Santa, all within a few blocks of each other.
Shop Local. Sip Local. Celebrate Local.