Winona, Minnesota doesn't show up on most Minnesota travel lists. It's not on the way to the Boundary Waters or the North Shore. It's not a suburb of Minneapolis with a good trail system. It's a small river city tucked into one of the most dramatic river valleys in the upper Midwest, doing its own thing quietly, and it's been doing it for a long time.
We live and work here. We think it's one of the best-kept secrets in the state. Here's why.
The Geography Is Extraordinary
Winona sits at a wide bend of the Mississippi where the river valley opens up and the bluffs rise on both sides — limestone ridges formed over millions of years as the river carved through sedimentary rock. The elevation gain from the river to the bluff tops is 500–600 feet, and from any of the overlooks, the view is the kind that stops you from talking for a moment.
This is the Driftless Area — the part of the upper Midwest that the glaciers missed, leaving behind a terrain of deep valleys, steep ridges, and clear-running creeks that look nothing like the rest of Minnesota. The karst topography means springs and sinkholes and caves alongside the more obvious bluffs and rivers. It's geologically unusual and visually remarkable.
The bluffs aren't just scenery. They create a microclimate, a sense of enclosure, and a reason to hike. From the valley floor looking up, they feel enormous. From the top looking down, the river curves through the landscape like something painted.
The Mississippi River
The river here isn't background. It's the point.
The Upper Mississippi National Wildlife and Fish Refuge encompasses hundreds of thousands of acres of river bottom land — islands, backwater channels, oxbow lakes, wetlands — and the Winona stretch is one of the richest sections. Bald eagles are year-round residents here in numbers that genuinely surprise first-time visitors; this stretch of river is one of the best places in the continental United States to see them.
The backwaters create a paddling environment that's calm enough for beginners and interesting enough for experienced kayakers. The fishing — bass, catfish, walleye, crappie — is some of the best in the Midwest. And the river as a visual and atmospheric presence is constant: you see it from the bluffs, you hear it at night, you feel it in the morning fog.
The Stained Glass Capital of the US
This is one of those facts that sounds like local boosterism until you see it. Winona has the highest concentration of antique stained glass windows in the United States. During the lumber boom of the late 19th century, Winona was one of the wealthiest cities per capita in the country — and its churches, public buildings, and private estates were built and decorated accordingly.
The result is a downtown full of extraordinary glass from some of the finest studios working at the height of the art form. The Winona Stained Glass Trail is a self-guided tour through the downtown churches and public buildings. It takes a couple of hours and is unlike anything else in the region.
The Cultural Life
For a city of roughly 27,000, Winona has cultural institutions that would be notable in a city twice its size.
The Great River Shakespeare Festival is the anchor — a professional summer theater company that produces world-class outdoor Shakespeare from late June through August. The performances take place in an outdoor venue with the bluffs in the background, and the quality of the productions regularly draws audiences from Minneapolis, Chicago, and beyond. For a small river city, having this is remarkable.
The Acoustic Café has been a live music and arts venue for decades, and it's the kind of place that small cities either have or they don't — a genuine gathering point with character and history. Winona State University and Saint Mary's University bring arts programming, gallery shows, and a university-town energy that keeps the cultural calendar full.
The Food and Drink Scene
Winona's downtown food scene is locally-owned in a way that's increasingly rare. The chain restaurants exist on the highway-adjacent strip, but the downtown core is independent shops and restaurants with distinct personalities. Jefferson Pub and Grill handles the casual dinner with river views. The Acoustic Café handles coffee and lighter fare with live music. A handful of other spots serve food that reflects local sourcing and genuine kitchen investment.
The Winona Farmers Market, running May through October on Saturday mornings, is the anchor of the local food culture — local produce, honey, cheese, baked goods, and crafts from vendors who know the region intimately.
The Outdoor Recreation
Everything is close together and accessible. From downtown Winona, you're 10 minutes from serious bluff hiking, 15 minutes from backwater paddling put-ins, 20 minutes from Great River Bluffs State Park, and 30 minutes from John Latsch State Park. Paved trail routes connect the area for cyclists. Fishing access is everywhere.
For a small city, the outdoor recreation density is exceptional — and none of it requires a permit application or a long drive.
The History
Winona was a major river town during the steamboat era, a lumber-boom millionaire's playground in the 1870s and 80s, and a layered immigrant city in the decades that followed. Polish, Czech, German, and later Hmong communities each left their mark on the city's culture, architecture, and food. The Watkins Heritage Museum tells this story well and is free to enter.
The historic downtown reflects the wealth of the lumber era in its architecture — brick buildings with ornate details that survive because Winona didn't get bulldozed for urban renewal the way some cities did. It's a genuinely intact river town.
The Scale
This is the underrated variable. Winona is small enough that you can understand it in a weekend — the downtown is walkable, the natural attractions are all within 30 minutes, the community feels actual rather than performed. But it's large enough to have things: restaurants, culture, a hospital, a university, a working downtown. It's not a museum town frozen in amber. It's a real place with real life in it.
Proximity to La Crosse
Twenty-six miles south on Highway 61 is La Crosse, Wisconsin — a city of 52,000 that gives you a second city's worth of amenities, a bigger food scene, and Grandad Bluff, which is one of the best overlooks in the entire region. Winona and La Crosse together cover the full range of what the Mississippi River bluff country has to offer, and staying at Camp Everyday puts you between them.
Use Camp as Your Home Base
Camp Everyday Winona is 6 miles south of Winona — close enough to be in the middle of everything, far enough that the campground has its own landscape and quiet. Book your site and use us as the launching point for everything the region has to offer.
Plan Your Stay
Ready to experience the bluffs for yourself? Book your site at Camp Everyday Winona.
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