It has titans of industry to rival New York and the most shoreline of any state in America. It’s the site of the first heart transplant and the first utterance of the phrase “Holy Cow.”
Minnesota is full of surprises, and we found our own in the small town of Winona.
As the peak of the fall colors approached in Southern Minnesota, Passion Passport founder Zach Glassman and Marketing Manager Jack Callahan set out from the Twin Cities and traced the Mississippi River. Heading south towards Winona, we had barely a weekend of collective Minnesota experiences to fall back on. Each turn down Highway 61, winding along the edge of the river beneath the bluffs, filled in a bit more of the blank map. 
Southern Minnesota is renowned, yet not all that well known, for its Bed and Breakfast culture. Hotels can be hard to come by, but walk a few blocks away from most small-town main streets and you’ll see illuminated living rooms and entryways dotting the streets. Long past 9:00pm, affectionately referred to as Minnesota Midnight, the Bed and Breakfasts stay open awaiting travelers from near and far.
We turned up late at The Historic Inn on Ramsey Street in Hastings. An immaculately renovated Victorian home, the building has been part of Hastings for over 100 years, having enjoyed prior existences as the town’s most opulent residence, as well as a private hospital. Having been thoroughly updated over the years, it fits in well in Hastings. The building hasn’t sacrificed any of its authentic character over the years.
The drive from Hastings to Winona is just about two hours. The occasional town crops up along the way, but most of the trip is through quiet farms and wooded hillsides. Small towns like Miesville and Read’s Landing, and even larger ones like Red Wing and Wabasha, whip by quickly. The only constant is the river, laying lazily next to you as you drive. Looking at a map, it seems like a direct, rather quick, trip. But in each town something catches our eye and entices us to pull off and explore. In fact, it took us two days to complete the drive.
A few turns down the river is Lake City, situated on Lake Pepin, the largest body of water on the Mississippi. A summer community with an avid boating culture, some locals continue to reside in town after the tourists and vacationers leave. One of the most pleasant surprises of the trip was Nosh, a restaurant right on the water’s edge where the kitchen is equally adept at Minnesota-staples like beet salad, or foreign imports like seared Foie Gras.
Other stops on the way to Winona include The National Eagle Center in Wabasha and Broken Paddle Guiding, a kayak tour company that leaves from Read’s Landing. We met up with Broken Paddle for a sunset tour of the river, winding their way up the backwaters searching for foliage. The edges of the river are flood plains, and if you come in the rainy season you’ll find yourself in the flood, kayaking through the forest halfway up the tree trunks. Because of the wet climate, the trees take on a soft yellow hue in the fall. Deep in the backwaters lays this floating home, off-kilter in the dry season, waiting for the flood.
Further down the river is Winona, a sleepy town of 30,000 people thats spreads out on an island in the river, able to be surveyed from Sugarloaf, a rock formation that sits atop the bluffs just out of town. There, we stumbled on our biggest surprise of the trip: the town is a bastion of culture, batting far above its population bracket. Dotting the well-planned street grid are authentic Prairie School-style banks, and fine art museums with the work of Matisse and Monet.
It is a place with roots, unlike some of the other small towns along the river which seem more temporary. While many feel like they swell and whither with the season or the economy, a visitor is confident that they’ll recognize Winona when they come back. And when they do come back, many stay.
The same backwaters that were deserted woods further north have been colonized outside Winona. Boathouses, as the locals call these floating homes, dot the shoreline and line the creeks as they curve into the forest. Some are new, with amenities like water-tight windows and wood stoves. Others are simple summer cottages, built with the supplies at hand. The Boathouses, unique to this part of the Mississippi, offer a nice microcosm of Winona itself: a little community tucked away on a forgotten corner of the river, overflowing with the idea that, regardless of location, life is what you make it. Whether it’s a bookstore/coffee shop hybrid that serves dinner two nights a week to fill up the cash-drawer, an opulent bank with an African taxidermy collection reminiscent of Theodore Roosevelt, or an extensive Ansel Adams exhibit at the local art museum, Winona has invented itself through the years. The result is a unique community, one worth a visit, that is well represented by its inhabitants, people who brave one Minnesota winter after another on small floating houses.
