November 7 – December 23, 2026
Discover the Spirit of Christmas in Downtown Baraboo
Shop local. Sip local. Stay awhile.
There is something special about Downtown Baraboo during the Christmas season. The storefronts are decorated, the Square is glowing and more than 40 locally owned shops, restaurants, coffeehouses and lounges are ready to welcome you.
This year, do more than make a quick shopping trip. Grab your favorite ladies or plan a weekend with your partner and stay awhile. Downtown Baraboo is an easy holiday getaway from Milwaukee, the Fox Valley, La Crosse and Dubuque, Iowa — and everything downtown is within a few walkable blocks.
From early November through Christmas, every weekend brings another reason to visit. Come shop, eat, sip and enjoy a Christmas weekend that does not feel rushed.
This Weekend
September 25–27
Planning your trip? Here is what is on while you are in town.
No events on the calendar this weekend — browse all upcoming events.
Plan a Weekend for Two
A Christmas getaway does not need an overpacked schedule.
Check into your hotel or cabin, then head downtown for an afternoon of shopping. Stop for coffee, find a few gifts, enjoy dinner and order a festive drink before walking through the lights around the Courthouse Square.
Make your way through the new Sip the Square Holiday Beverage Tour, featuring ten downtown coffeehouses, bars and lounges with special seasonal drinks. Pick up a passport at your first stop and complete the tour over one weekend — or save a few stops as an excuse to come back.
The next morning, sleep in a little, grab breakfast or brunch and head back downtown to visit the shops you missed the day before.
Gather the Ladies and Make a Weekend of It
Some of the best Christmas traditions begin with a group text.
Invite your sisters, daughters, girlfriends or favorite shopping partners and meet in Downtown Baraboo for a weekend away. Start with coffee and spend the day exploring locally owned boutiques, galleries and specialty stores filled with clothing, jewelry, home décor, books, art, specialty foods and gifts you will not find everywhere else.
Stop for lunch when you need a break. Drop your bags off at the hotel, freshen up and meet back downtown for dinner and cocktails.
The Santa’s Night Out Winter Wine Walk is a great excuse to plan the trip. Dress as your favorite version of Santa and spend the evening sampling wine while shopping your way through more than 20 participating downtown businesses.
Staying overnight means no rushing home and no trying to fit everything into one afternoon.
Stay Overnight in Baraboo
Your holiday getaway can be as cozy, historic or comfortable as you want it to be. Baraboo offers several places to stay close to downtown, with options for couples, groups and anyone who wants to turn a day of shopping into a full weekend away.
Once you have a room booked, round out the trip with a massage or spa visit, a scenic drive through the Baraboo Hills, or a stop in the Wisconsin Dells nearby.
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.
Seven weekends to choose from
Pick the weekend that fits your group
The full calendar of markets, wine walks, parades and more — see what is happening the weekend you are thinking of staying.
Shopping Feels Different Here
Downtown Baraboo is not a shopping center filled with the same stores you can find anywhere. Our downtown businesses are locally owned, and the people behind the counter are often the same people who selected, made or ordered everything you see.
You will find thoughtful gifts, locally made products and plenty of unexpected things you did not know you were looking for. Park once and walk between dozens of shops, restaurants, coffeehouses and lounges surrounding the historic Courthouse Square.
And when you shop here, your purchase stays here — supporting local business owners, their employees and the people who continue to invest in Downtown Baraboo.
Make Downtown Baraboo Part of Your Christmas Tradition
The best holiday traditions do not need to be complicated. Sometimes it is simply a good meal, a little shopping and time with the people you enjoy most. Come with your partner. Bring your sisters, daughters or girlfriends. Stay overnight, shop local and discover why Downtown Baraboo feels a little more special at Christmas.
Shop Local. Sip Local. Celebrate Local.