Discover the Spirit of Christmas
Christmas in Downtown Baraboo
Seven weekends of holiday magic, November 6 – December 31, 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. Book lodging and stay for a few days to experience it all.
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. Find the perfect lodging accommodation from cabins and inns to bed & breakfasts and hotels.
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.
Every day, Nov 6 UNTIL DEC 31
SIP the square & light up the Square
Sip festive holiday beverages at shops downtown via our Sip the Square Beverage Tour. Pick up a passport at participating locations and start your tour with a delicious holiday cocktail or warm peppermint hot cocoa.
Don’t miss out on seeing Light Up the Square, an incredible holiday lighting display surrounding the Sauk County Courthouse 7 days a week Nov 6th to New Year’s Eve 5pm to 10pm.
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.
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Countryside Refind Holiday Open House
🎄Join us for our BIGGEST event of the year! Our Holiday Open House will be here before you know it!
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Spa Serenity Holiday Sock Launch
SPA SERENITY HOLIDAY SOCK LAUNCH! The most wonderful time of the year is getting a whole lot COZIER!
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,…
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Christmas Light Parade
The Christmas Light Parade features more than 60 dazzling community, business, and corporate floats, each glowing with thousands…
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. Stay for a few days to experience it all.
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. It’s the perfect overnight getaway.
Shop Local. Sip Local. Celebrate Local.
Thank you to Travel Wisconsin for supporting our 2026 holiday marketing.