Cradled by the Mississippi River on one side and 500-foot-tall bluffs on the other, Winona is an astonishingly beautiful, unexpectedly cosmopolitan city that is as legendary for outdoor recreation as it is for its arts scene. For outdoor enthusiasts, it is surrounded by some 20,000 acres of public lands that provide endless hiking, biking, climbing, birding and paddling trails.
Arts lovers by the thousands trek to Winona to take in its national Shakespeare festival, international classical music performances, world-class art displays and deep roster of festivals and live music events throughout the year. An exploding foodie and craft cocktail scene have helped it become one perfect little city in the Southeastern corner of the state.
Scroll through the gallery below to find ideas for the perfect itinerary in Winona.
Located on what was once an island in the Mississippi River, Winona is a historic river city with towering bluffs and beautiful views.
2. Historic Downtown Winona
Milling and lumber trade made Winona a wealthy port city 150 years ago, and evidence of that grandeur can be appreciated throughout our beautifully preserved historic downtown. Grab a historic walking tour map from the Visitor Center or the Winona County History Center and stroll the magnificent architecture.
3. Lounge in Lake Park
Lake Park has more than 1,000 acres of land and water available for outdoor fun. Our nearby landmark rock pinnacle—Sugarloaf—sits about 500 feet above the city and includes hiking/biking routes with sweeping views of the river valley. Photo by Mary Farrell
4. Unique Local Flavors
We like great food in these parts and Winona has no fewer than 40 unique local eateries. Interesting takes on American and farm-to-table cuisine and craft cocktails are getting people like Andrew Zimmern excited about Winona’s food scene, and our authentic international kitchens are pure delight as well. Photo credit: Muddled Thyme
5. Great River Shakespeare Festival
Plan to be in Winona between June 20-July 30 to take in a play by one of the finest Shakespearean theater companies in the country. With a national cast and an approach that aims to make Shakespeare fun for even non-theater lovers, GRSF entertains more than 10,000 people annually. Photo credit: Great River Shakespeare Festival
6. Great River Road Wine Trail
The Great River Road has been called one of the country’s most scenic byways, and the Great River Road Wine Trail might be the best reason to cruise it. Winona is the perfect homebase to enjoy the 10 wineries that comprise the trail, with several just minutes from downtown. Photo credit: Elmaro Vineyard
7. Music and More Music
From classical performances by world-renowned musicians to indie music festivals and everything in between, Winona is alive with music year-round. Outdoor venues such as the Historic Band Shell and the Levee Park Stage compliment more intimate spots to offer myriad different music vibes for audiences large and small. Photo by Cynthya Porter