Southeastern Minnesota’s Secret Playground


Attention outdoor recreation junkies 

We are about to let you in on one of the Midwest’s best-kept secrets 
Winona bluffs with fall colors rise above clouds

The dramatic bluffs of the Driftless Region are unlike anywhere in the Midwest

Thanks to a freak of nature during the last ice age, there is a stretch of land in Southeastern Minnesota that is an unspoiled paradise for bikers, hikers, climbers, and paddlers, but many have never heard of it because those in the know keep it like a closely guarded secret. And with good reason: It is a region with towering bluffs, hundreds of miles of trails, and a maze of Mississippi River backwaters – a jarring and beautiful contrast from the hundreds of miles of flat terrain around it. For those who discover it, the area makes a premier playground available with a short drive from anywhere in the Upper Midwest. 

The dramatic landscape – called the Driftless Region – along a small stretch of the Mississippi River is made possible by a peculiar event 10,000 years ago or so when glaciers were inching their way across the North American continent. For reasons scientists still debate, the glacier parted in the southernmost corner of Minnesota and left a piece of land undisturbed there, with the two sides of the glacier rejoining in Iowa. While everything around it was crushed flat and covered with sediment, this region kept its rugged bluffs and deep valleys that more resemble northern shores of the Great Lakes than America’s Heartland.  

An aerial view of Winona shows Sugar Loaf rising high above the cityPerched on the Mississippi River just off of Interstate 90 in Southeastern Minnesota, Winona, Minnesota, is one of the most scenic cities in the Driftless Region and it has become a hub of sorts for the various recreational amenities the area has to offer. Located two hours from Minneapolis and Saint Paul, two and a half hours from Madison, three and a half hours from Des Moines and four and a half hours from Chicago, its central location makes it an easy road trip for visitors from across the Midwest coming to explore the pristine natural resources there.

mountain biking, biking, bluffs, winona

Exhilarating trails bring riders from across the country to Winona

Road riding and mountain biking have attracted some international attention for the city, with international legend Greg LeMond using the city’s bluff roads to train for Tour de France and numerous national-caliber road and mountain biking races occurring there in recent years. The bluffs and river valley that cradle Winona are crisscrossed with more than 100 miles of trails made for exploring, including gentle doubletracks over rolling terrain to adrenaline-pumping singletracks that rocket from high in the bluffs.


Exposed rock faces extending hundreds of feet in the air have lured climbers from across the Midwest, and a new ice park for winter climbing keeps them coming year-round. A pinnacle called Sugar Loaf that rises some 500 feet over the city has numerous routes placed by professional climbers, and a local guiding company is on hand to help newcomers scale the bluffs and ice flow safely. 

For paddlers, the backwaters of the Mississippi River along this stretch are a maze of quiet trails around islands and sandbars where thousands of migratory birds can routinely be seen. Even better, virtually every island and sandbar on this stretch of river is public land thanks to a donation by a local eccentric 100 years ago, and paddlers are welcome to pull up anywhere and sit for a spell or even pitch a tent and camp if they want to. Seasonally, Prairie Island Campground has canoes, kayaks and standup paddleboards available for rent with access to the backwaters via their beach.

Beer taps at Island City Brewing Company pour unique microbrews

When the day is done, Winona has a hefty list of new and long-standing eateries and drinkeries, each with its own unique local flair, as well as a downtown brewery and a collection of local wineries that add eclectic flavors to the landscape. And the city is known for its music and arts scene, with ten annual festivals and live music happening all over town to fill the recreation hours not spent on the bluffs or river.

And in what is sure to be a boon for the city, local officials and outdoor rec lovers have collaborated to build more recreation infrastructure than anywhere around it, including the ice park located on a bluff within city limits, new bike trails, and new rental programs that allow people to experience the great outdoors without bringing bulky equipment with them. A $23 million parks plan recently unveiled by city leaders aims to take the city even farther as a premier recreation destination. The time to discover this area is now because, with everything that’s happening now, down the road it’s likely to be the Midwest’s least kept secret.