Owatonna, Minnesota, is a masterclass in how a small city can deliver big-city flavor and world-class culture without losing its Midwest soul. Whether you’re an advocate of historic architecture, a trail runner, or someone who simply lives for a legendary fair, Owatonna offers a dense collection of experiences.

A Culinary Tour: 30 Ways to Eat Local

One of Owatonna’s best-kept secrets is its robust dining scene. The city boasts over 30 locally owned and independent restaurants, meaning you can skip the chains and still never eat the same meal twice.

  • Global & Local Flavors: From wood-fired and specialty pizza at local landmarks to authentic Mexican cantinas serving up street tacos and rich moles, the variety is staggering. You’ll find upscale American bistros and classic diners, and Asian fusion spots that bring a contemporary edge to the downtown area. Grapeful Wine Bar, showcases the best of local winemaking talent by always offering a featured local wine.
  • The Sweet & The Suds: For a true local tradition, head to the city’s iconic chocolatier, Costas Candies, famous for their hand-dipped chocolates and that have been crafted here for over a century. If you prefer your calories in liquid form, the local brewery, like Mineral Springs Brewer, offers a rotating tap list that perfectly pairs with the community’s social energy, and offers pieces of history in the names of their craft beer.

Architecture and Iconic Attractions

Owatonna’s downtown isn’t just a place to shop; it’s a National Historic Landmark. The crown jewel is the National Farmers’ Bank, often called the “Jewel Box of the Prairie.” Designed by the legendary Louis Sullivan. Its stunning gold-leaf arches and stained-glass windows make it one of the most important architectural sites in the United States.

Just outside the downtown core, you’ll encounter the city’s unique history at the Minnesota State Public School Orphanage Museum. It is one of the only museums of its kind, telling the poignant and ultimately hopeful stories of the 10,000 children who lived on the campus between 1886 and 1945. Nearby, you can pay your respects to the Princess Owatonna statue at Mineral Springs Park, a tribute to the legend of the Native American princess said to discover the healing properties of the local waters.

You’ll be delighted with the productions of local talent at the Little Theatre of Owatonna, and time will pass quickly while you visit the Owatonna Arts Center’s monthly exhibit.

Miles of Trails and Annual Tradition

For those who prefer the great outdoors, Owatonna is woven together by miles of interconnected trails. The Kaplan’s Woods Parkway offers nearly seven miles of hiking and mountain biking paths that wind through dense forests and over the Straight River, connecting seamlessly with additional miles of trails to other city parks.

Finally, no visit is complete without mentioning the Steele County Free Fair. As Minnesota’s largest free fair, it draws hundreds of thousands every August (scheduled for August 18–23, 2026) boasting a massive Midway, and enough food stands, and popular grandstand shows to make even the most seasoned fairgoer’s head spin. Next door to the fair is Steele County History Center’s “Village of Yesteryear” where you can learn more about the early settlers of Steele County.

Owatonna manages to be both a quiet retreat and a vibrant destination—a place where history is preserved in stained glass and the future is toasted with a local pint.