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Have a Cozy Weekend in Baraboo

In a recent episode of The Cabin podcast, Josh Ostermann said, “You have to live like a tourist where you are.” And I FELT THAT! Never stop exploring–even if the adventure is just in your own backyard! Just because we live in Baraboo doesn’t mean we can’t find new ways to explore it. We love our town, and it’s truly magical this time of year. This staycation reminded us just how lucky we are to live here!


We spent two nights at The Ringling House Bed & Breakfast. It’s so cute, in a great location, and was originally the home of Charles Ringling (one of the Ringling brothers who started the circus!). Our room was beautiful and it was so cool to see the inside of this historic building!


Start your day at the fabulous Coffee Bean Connection and cozy up with a warm beverage before exploring downtown. Everything is so fun and flavorful, and all Barabooians know and love the fun little stickers Coffee Bean gives out to cover the lid hole to keep your drink warm!


There are so many terrific restaurants in Baraboo, but over this staycation we really enjoyed Little Village Cafe for lunch. The Little Village has a wide variety of food on their menu, and we always get their incredible potstickers as an appetizer. Hayden loves their burritos, and I’m always down for their soup of the day.

While we frequently visit Baraboo Burger Company on any given week, this visit was all about the Burger of the Month! They are featuring a Green Bean Casserole Burger this November, and Hayden loved it!! The Burger of the Month is always super creative and delicious, and I highly recommend checking it out when you visit.


There are lots of ways to drink locally in Baraboo! Our favorite spot for a date night is Driftless Glen Distillery. Not only do they have a fantastic, massive cocktail menu, but they also have delicious food and weeknight drink specials! We love all the appetizers– but specifically the pinsas and sliders, as they are perfect for us to share while we chat and enjoy a cocktail.

Tumbled Rock Brewery & Kitchen has 20 beers on tap, and they absolutely slay the food game as well. Their menu is very unique– Hayden loves the “My Bologna Has A First Name” which is a grilled bologna sandwich. I love their French Onion Soup–they nail it every time! Tumbled Rock also was awarded best cruds in Baraboo by not only us, but The Wisconsin Cheese Queen.

If you’re looking for a place to relax after dinner, we highly recommend Con Amici Wine Bar for an after dinner drink. The vibe is cozy and they often have live music. Grab a glass of wine or a seasonal cocktail (right now they have their Peppermint Bark-tini…highly recommend it!) and relax in the lounge area or head to a table to play one of the many games they have available!

Balance Rock Winery is another one of Baraboo’s fabulous establishments. They have wine flights and you seriously can’t go wrong with any of their snacky apps! My favorite wine is called “Brianna,” but I must say, the wine cocktails are the hidden gem of Balanced Rock! They rotate with the seasons, but are always so good. The white wine cocktail right now is “Golden Apple Fizz,” and I can’t recommend it enough!


How could you come to Baraboo and not explore the incredibly beautiful bluffs?! Bundle up for a beautiful hike (or snowshoe) on the Ice Age Trail. We did a chunk of the Devil’s Lake Segment at Steinke Basin— It was so stunning all covered in snow! If you’ve never seen a snowy Devil’s Doorway before, you should absolutely take the hike up East Bluff of Devil’s Lake State Park to check it out. It’s crazy beautiful, but make sure you have waterproof hiking boots! The grip will come in handy up there. These are the boots I currently have and I absolutely love them. They are completely waterproof even when we snowshoe!


For $1 you can take part in one of my favorite thrills of Baraboo! Okay… that might be a little bit dramatic, but you should still stop into BaraBrew Wine & Spirits to try the mystery beer machine! It’s so fun and you never know what you’re going to get. Could be Hamms, Gumball Head, Busch Light, or Fantasy Factory.. Oh my!


Downtown Baraboo is full of the cutest shops! You can’t go wrong with holiday shopping on the square. Here are a few of my favorites-

Bekah Kate’s: They have all the kitchen gadgets, holiday hosting necessities, and even some gourmet food mixes! Lots of great gift options too.

Spa Serenity: It’s always filled with such fun stuff, but they really do have a gift for everyone stocked right now! From cocktail kits to 2023 planners, everything is unique and beautiful.

Countryside ReFind: Another favorite of mine! They have incredible home decor and lots of festive kitchen accessories.

Just Imagine: This toy store will blow you away! It’s full to the brim with gifts for kids of all ages and games for the family.

Fetch 22: Great for picking up some festive treats or new toys for the pups. They carry anything your adventure buddy could ever need!

A Sense of Adventure: This store is full of gorgeous Fair Trade products. My mom loves their handmade jewelry!

Spirit Lake Trading Company: A downtown gem stocked with handmade and natural products/gifts.

With so many great shops right in town, you can knock out so much holiday shopping in one trip!

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