Discover Real Baraboo: Itineraries Inside!

Hailey Rose

March 27, 2026

Baraboo, Wisconsin, is where history, nature, and small-town charm come together in the most magical way! Whether you love circus fun, family adventures, scenic hikes, shopping downtown, or tastings at local breweries and wineries, you’ll find it all right here. Read on to start planning your perfect Baraboo getaway!

Discover The Circus Heritage Trail

Photo Credit: Discover Mediaworks

Calling all circus lovers and history buffs! Step right up! This itinerary brings the Big Top legacy to life.

Start your adventure at the Circus World Museum, where the Ringling Brothers’ story all began. Known as the Famous Five, the Ringlings started in small-town Baraboo and rose to captivate audiences across the globe! Their legacy still lives on here, and you’ll find traces of their story everywhere you look!

Next up, take a tour (or plan an unforgettable overnight stay) at the amazing Al. Ringling Mansion. Another historic stay worth mentioning is the Ringling House Bed & Breakfast! Then, sample craft brews at the Al. Ringling Brewery, featuring the original family recipe and one-of-a-kind memorabilia. In fact, they house the world’s largest collection of Ringling family artifacts congregated in one place.

Downtown, make sure to see a show at the Al. Ringling Theatre, a 1915 palace of the arts that still enchants audiences to this day! The theatre brings in an array of top-notch performances, from professional acts to community dance groups. If you want to make the show an even grander experience, hobnob in the Ladies’ Lounge or watch from a luxurious box. 

While Baraboo certainly celebrates its circus heritage every day, you have to visit in the summer and catch the Big Top Parade, where thousands come to celebrate the community and its rich, cherished traditions! It’s a total throwback to circus days—it even features incredible cyclists who ride the same historic bicycles from 1888! 

Plan a Family Fun Day

Photo Credit: Discover Mediaworks

Bringing the littles? Baraboo offers fun for all ages with the perfect mix of play, learning, and nature.

Start your adventure at Ochsner Park Zoo, open year-round with free admission… That’s right, free! Meet more than 30 different species, including emus, black bears, and even Arctic foxes. Fun fact: about 70% of the animals here are rescued or rehabilitated! You can even book a behind-the-scenes tour for an up-close encounter with these furry (and feathered) friends.

Can’t get enough animal time? Make your way to the International Crane Foundation, the only place in the world where you can see all 15 species of cranes in one spot! But if the weather doesn’t cooperate, take the fun indoors at the Baraboo Children’s Museum, perfect for ages six months to 12 years. 

Before the next stop, make a sweet pit stop at the Baraboo Candy Company, home of the famous Cow Pie chocolates and other nostalgic goodies. It’s the perfect place to grab a treat (or two) before the next activity on the itinerary.

Top it all off with a magical day at the Circus World Big Top Show, where jaw-dropping acrobats and out-of-this-world performances bring circus excitement to life for the whole family. There’s truly fun for all generations in Baraboo! 

Escape Together in the Baraboo Hills

Photo Credit: Discover Mediaworks

Have you been dreaming of a magical couple’s retreat? Make those dreams come true in Baraboo at the Inn at Wawanissee Point, located in the breathtaking Baraboo Hills—one of the oldest mountain ranges in the world! 

This adults-only retreat offers exceptional hospitality and picturesque, panoramic views, with four distinct guest rooms, each holding a unique story and style. You don’t just admire nature, you truly become part of it! During your stay, hike the scenic trails, snap a few photos, and escape from the everyday.

For ultimate relaxation (and the perfect finishing touch on your Baraboo Hills escape), slip away to Spa Serenity, where luxurious treatments and tranquil surroundings help you relax, reconnect, and recharge. 

Pack Your Day with Outdoor Adventures

Photo Credit: Discover Mediaworks

For fresh air and endless fun in the great outdoors, Baraboo is the perfect destination for every explorer. From hiking and rock climbing to scuba diving and golfing, your next epic adventure begins here.

Start off easy with a stroll along Baraboo’s scenic Riverwalk, a paved path that winds along the Baraboo River. Walk, bike, fish, or simply soak in peaceful views of the water and surrounding natural beauty. 

If you’re craving a thrill, tackle the cliffs at Devil’s Lake State Park, Wisconsin’s most-visited park, and for good reason. With 29 miles of trails, stunning rock formations, scenic overlooks, and two beautiful beaches, it’s a natural playground that never gets old! 

Want to explore beneath the surface? Dive into a one-of-a-kind freshwater experience with Breezeway Bubbles Scuba, where curious fish, including smallmouth bass, and hidden treasures await. What will you find? 

Back on land, tee off at Baraboo Country Club, Devil’s Head Resort, or Fairfield Hills Golf Course, all three offering pristine greens and panoramic views. Looking to test your skills in a different way? Head to Dez Tactical Arms for safety-certified training sessions, a state-of-the-art indoor range, and hands-on education for responsible firearm use. It’s for first-timers and seasoned shooters. 

Take a Baraboo Boutique Stroll

Photo Credit: Discover Mediaworks

Time to shop ’til you drop, and there’s no better place than Baraboo, home to a wonderful lineup of locally owned boutiques, all scattered throughout the historic downtown!

Start your stroll at Johnny’s Girl Boutique, where style meets small-town dreamer. From businesswear to can’t-beat casual looks for new moms and everyone in between, this shop offers clothing for everyone. And be sure to check out the curated selection of accessories to match! 

Next, pop into Angels & Arrows Boutique, known for its women’s contemporary fashion. You’ll find shoes, handbags, clothing, and accessories in styles that range from everyday essentials to bold statement pieces. 

Shopping for the kiddos? Add Just Imagine Toys to your list. This whimsical wonderland is filled with toys, books, and games that spark creativity for kids (and kids at heart). It’s definitely a must-stop, especially for families exploring downtown.

Then, swing by Bekah Kate’s Kitchen, Kids, & Home—a culinary lover’s dream. Packed with gourmet ingredients, kitchen tools, and gifts for foodies of all kinds, it’s a store that truly feels like home. 

End your shopping trip at none other than The Jewelers Edge, a full-service jeweler specializing in custom designs and repairs. And ladies, you have to ask about their Simply Baraboo Collection, crafted exclusively for the store and inspired by local landmarks like Devil’s Doorway and Balanced Rock. It’s the perfect souvenir to remember your trip.

Embark on the Foodie & Beverage Trail

Photo Credit: Discover Mediaworks

Foodie and beverage enthusiasts, this one’s for you! Follow Baraboo’s flavor trail and taste your way through local favorites.

Kick things off at Gina Jenny’s, a charming wine and cocktail bar and lounge right downtown. Then, make your way to Tumbled Rock Brewery & Kitchen, a woman-owned and woman-brewed gem where the beer couldn’t get any fresher. It’s actually made on-site, pegged, and poured straight through the taps you see. For Tumbled Rock, beer isn’t just a drink; it’s a way to bring people together.

Up next, head to Driftless Glen, a riverside distillery and upscale restaurant known for creative cocktails, award-winning spirits, and a menu that features local ingredients. Continue your trail to Balanced Rock Winery, a family-owned boutique winery pairing scenic views with an incredible selection of wines.

Finally, raise a glass at Baraboo Bluff Winery, home to Sauk County’s largest vineyard. This veteran- and family-owned spot offers its own lineup of award-winning wines and sweeping views you simply can’t miss. 

Ready to discover real Baraboo your way? With so many ways to explore, there’s no wrong path here! So be sure to pack your curiosity, follow your interests, and let Baraboo surprise you! 

For a glimpse into Baraboo’s magic, watch Discover Wisconsin episode “Wisconsin’s Circus Town & Outdoor Playground — Baraboo” below: 


Hailey Marien: Writer for Discover Mediaworks. A born & bred Wisconsinite with a love for fishing, hunting, and enjoying the great outdoors.

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