In a state best known for wide-open skies and endless cornfields, Osage delivers a completely different kind of Midwest story. This town in North Central Iowa has just 3,500 residents, yet is home to one of the Midwest’s most surprising culinary scenes—complete with a 24/7 speakeasy and a chef redefining what farm-to-table means.

Osage also supports a downtown that’s both vibrant and unexpected. It’s a place where you can sip craft beer at Limestone Brewers, enjoy a chef-driven meal at Taste of Osage, browse indie shops full of unique goods, and even step back in time at a retro drive-in.

This article is sponsored by Evolution of the Heartland. All opinions are mine.

🧳 When You Go: Osage, Iowa

Osage is not the Iowa of truck stops and chain restaurants. This tiny town is something entirely different. There are so many reasons we think you will enjoy visiting this small town!

📍 Location: Mitchell County, North Central Iowa — about 45 minutes from Mason City, 2 hours from Des Moines, and 2 hours from the Twin Cities.

👥 Population: 3,500

🚗 Getting There: Accessible by car via Highway 9 or Highway 218. Nearest regional airport is in Mason City.

✨ Highlights:

• Chef Jes Baldus’ reservation-only Taste Osage Progressive Dinner
• Craft beer and ax throwing at Limestone Brewers
• Shopping on Main Street and beyond
• Nostalgia at Stan’s Drive-In
• Historic Watts Theatre and Cedar Valley Seminary
• Unique stays at the Teluwut Airbnb or the Airbnb above Watts Theatre

📅 Don’t Miss: The Evolution of the Heartland Immersive Tour on September 19 — a great chance to experience Osage like a local.

Jes Baldus – The Chef Who’s Changing the Town

Of the many things to do in Osage, Iowa, you’ll definitely want to say hi to Jessica Baldus, owner of Taste: Osage. Jes is an approachable Iowan who operates dining establishments unlike anywhere else in the area. Forget walk-ins or traditional menus—Baldus runs reservation-only monthly themed Progressive Dinners and Chef’s Table experiences at her restaurant Taste: Osage.

This dining experience showcases hyper-local ingredients you might expect in Minneapolis or Chicago. Her seasonal approach means the menu changes constantly, driven by what’s growing within a 50-mile radius.

Baldus doesn’t want to be fancy. She wants to be real. That realness translates into surprising dishes: think simple syrup made and delicate cake, both made with sweet corn during the summer growing season.

The dining experience extends beyond Taste Osage. Baldus owns three more completely different types of eateries. The first is Piggyback Smokeshack, a pop-up restaurant with a ghost kitchen. In the alley behind Taste: Osage, you’ll find barbecue with an attention to wood and timing that rivals Kansas City institutions.

Her third endeavor is the The Market – Osage. The Market functions as both a grocery store and community gathering place. Here you’ll also find the Bakery where you can get a slice of the homemade cheesecake that helped launch Baldus into fame. You can also buy cooked to order meals to enjoy at home.

But perhaps most intriguing is her fourth endeavor, the Blind Pig Speakeasy. Hidden from the public in the basement under Taste Osage is a genuine 24/7, members-only space that operates by invitation and referral. The only way in? Be a member, know a member, or book one of Taste’s progressive dinners. It’s the kind of place that shouldn’t exist in a town of 3,500, which is precisely why it does.

Purusing Osage’s Indie Shops

Osage’s downtown is full of unique, independently owned shops where you’ll find a lot surprises.

• Create features art and gifts made by local artisans.
• Shop on State, housed in a historic school building, is a huge thrift store that gives back to the community.
• Bo-K’s & Rusticks sells handmade wooden décor and offers a cozy wine room—locals swear by their wine slushies.
• Kountry Kupboard, run by a Mennonite family, blends a coffee shop with bulk groceries and handcrafted goods.
• Maxine’s on Main, Osage Floral & Gifts, and S&S Meats & Spirits round out a shopping district that mixes practicality with charm.

For a dose of nostalgia, head to Stan’s Drive-In, one of the few remaining drive-ins in Iowa, where burgers and ice cream sundaes come with a side of retro flair.

Other Things to do in Osage Iowa

Beyond dining and shopping, Osage has cultivated experiences that connect visitors to local culture. At Limestone Brewers, craft beer fans can sample small-batch creations in a welcoming taproom. Nearby, Stillwater Greenhouse and Twisted River Farm highlight the area’s agricultural roots with locally grown plants and produce. Active travelers can explore the Cedar River Complex, an indoor recreation facility with swimming and fitness amenities.

The Cedar Valley Seminary, a historic educational institution, now serves as a cultural programming hub with a mission to feed the area’s elderly population and houses a fantastic coffee house!

The historic Watts Theatre, painstakingly restored to its 1950s grandeur, screens both current films and family favorites. Staying in the Airbnb apartment above the theatre means falling asleep to the sounds of a town that still believes in downtown as a gathering place.

An Immersive Evolution of the Heartland Experience

Osage is a great place for casual exploration. But if you’re looking for structured activities, check out Evolution of the Heartland’s Immersive Tour of Osage on September 19. This curated experience goes beyond sightseeing—it connects you directly with the makers, farmers, and entrepreneurs who shape Osage. Guests will:

• Learn how rural communities like Osage thrive by blending tradition with innovation.
• Meet Chef Jes Baldus and sample her culinary creations.
• Explore Main Street shops and meet the families behind them.
• Taste craft beer, local meats, and handmade treats.

Learn about Evolution of the Heartland and buy a ticket here!

Where to Stay in Osage

We stayed in the super cuteTeluwut Airbnb, above the popular pub of the same name. It was a great home base within walking distance of many of the stores and restaurants we visited.

There’s also an Airbnb apartment above Watts Theatre called Watts Theatre Apartment Over Main with a private movie viewing space!

For travelers who collect unusual places, Osage represents something increasingly rare: a small American town that has figured out how to thrive by embracing what makes it distinctive rather than trying to be somewhere else. It’s the kind of place that reminds you why the journey sometimes matters more than the destination.

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