Discover Downtown Baraboo – date day

Dating in Downtown Baraboo has never been more exciting! No matter the season, there is a fun and romantic day to be had with your significant other. Start planning your next date day here in Downtown Baraboo!


There’s truly no better way to start your day! Grab a cup of coffee at one of our local coffee shops. The Coffee Bean Connection has been waking our community up for over 10 years and offers freshly brewed flavors each morning. If you love what you taste, shop their bulk tea, chai, and coffee selections procured from all over the world.

Step into the newly remodeled carriage house that is the Bella Vita Café to experience a slice of “The Beautiful Life.” Your nose will lead your decision in choosing a freshly made quiche, frittata, scone, biscotti, morning bun, or savory croissant. Enjoy fair trade coffee inside their cozy space, or in their courtyard.


When there are just too many places you’d like to dine, we suggest a restaurant crawl! Choose a different course or meal from each restaurant on your list. Here are just a few recommendations to indulge with your date. 

Breakfast begins at Jen’s Alpine Cafe. You’ll find all your favorites on the menu, including exceptional omelets, biscuits and gravy, eggs benedict, breakfast sandwiches, breakfast burritos, and more. If you’re not drooling yet, try their famous French toast or buttermilk pancakes! Jen’s also serves up a classic lunch & dinner menu.

What’s more romantic than Italian cuisine? MaMa Mia’s Pizza offers New York style pizza pies, pasta, calzones, and stromboli. 

Don’t miss the Little Village Cafe, a restored 1940’s diner with original décor. The menu is vast, unique, and absolutely outstanding. Have a glass of wine or beer, and experience dishes like Blackened Salmon, Moroccan Chicken, Mahi Mahi, Jamaican Jerk Chicken Burrito, or the Village Cheesesteak Sandwich. Homemade desserts are listed daily.


The Downtown Baraboo event calendar is jam-packed, especially in the warmer months, with the Baraboo Farmer’s Market, Baraboo Concerts on the Square, and Downtown Baraboo Sunday Markets! Our square transforms into a bustling display of art, food, music, and festivities with every event. If your stay lines up with these events, add them to your date day! We have an impressive collection of local growers, makers, bakers, musicians, and artists to introduce to you.


If your date day includes a trip to neighboring Devil’s Lake State Park, be sure to stock up on picnic goods from Bekah Kate’s Kitchen, Kids & Home! Grab a bottle of wine, crackers, dip, nuts and chocolates. While you’re at Bekah Kate’s, track down their featured Wisconsin goods, and other foodie favorites. There will always be friendly faces ready and willing to share their recommendations! 


Taste the region with Balanced Rock Winery! This winery features cold-hardy grape varietals that you’ll be able to enjoy in the tasting room or on the outdoor patio. Just moments from Devil’s Lake State Park, the views and ambiance are something to adore. In addition to their growing wine lineup and light fare menu, Balanced Rock hosts live music, and has an onsite Driving Range! Bring home your favorite bottles to commemorate your day.

As the AL. Ringling Mansion, (built in 1906,) was being restored, a folded piece of paper was discovered. That piece of paper contained “The Ringling Family Original” beer recipe, and thus— the AL. Ringling Brewery began. History runs rich through this beautiful brewery. Try the Ringling Original, or try one of the rotating specialties on tap. If you’re first-time visitors, try the iconic Mustache Flight! After beer tasting, fill up on their American, Paraguayan, or German specialty dishes. Live music & entertainment happens often!

Nestled on over two acres just outside the North entrance of Devil’s Lake State Park is Tumbled Rock Brewery & Kitchen. This craft brewery has an incredible atmosphere. Start in the open-concept restaurant, brewhouse & taproom, or tremendous patio & greenspace. Try the Tumbled Rock flagship or go with an adventurous seasonal brew. Their menu is described as old-world and home food with a full-flavor, modern twist. Apps, greens, soups, sandwiches, Friday fish frys, and the ultimate wood-fired pizzas are all date day tested and approved!


Connect with a Couples Massage at Spa Serenity for an experience that will leave you both serene and relaxed. Each massage is customized to focus on your body’s unique needs. Upgrade to enhance your spa experience with a Spa Package, including both massages and facials. You’ll love the tranquil environment and the way you feel!

Pro tip— Be sure to book your spa experience in advance!


If planning your date day looks more like a date weekend, you must book a romantic stay at the Ringling House Bed & Breakfast. This Georgian Revival home was built in 1901 by Charles Ringling, one of the founders of the Ringling Brothers Circus. This grand and historic accommodation will be one to remember. Additionally, by staying at the Ringling House, you’re helping to preserve a beautiful part of Baraboo history.