Start with a drive up to Garvin Heights, a bluff overlooking Winona, to get a feel for this so-called Island City. You can see the lake, park and the Mississippi curving through the valley.
Nearby, Garvin Heights Vineyards makes more than a dozen wines using grapes such as Minnesota’s Frontenac, Marquette, St. Pepin and La Crescent. Grab a bottle and some crackers and cheese to nibble on the deck, which has a 7-mile view.
Head to the Winona County History Center in Winona’s downtown and learn how the area boomed in the late 1800s. Then go on a self-guided walking tour (brochures available in the seasonal visitors center on Huff Street) to admire stained-glass masterpieces, ornate banks, and buildings like the world headquarters for J.R. Watkins, an 1868 door-to-door company selling spices, extracts, and fragrant personal care products and soaps.
Don’t miss the free Watkins Heritage Museum, which shows how products evolved from health tonics to trendy cosmetics.
Another specialty museum, Polish Cultural Institute of Winona, celebrates the Poles’ arrival for the 1870s lumber boom and how this group added to the local culture.
Winona’s most impressive museum sits along the riverfront. Minnesota Marine Art Museum devotes itself to paintings, photography and sculptures reflecting life on rivers, lakes and oceans.
Head into the bluffs on the outskirts of Winona for a tasty, innovative meal at Signatures Restaurant. Look for seasonal choices, such as lamb chops with ramps or pork ribs with a smoked peach chipotle sauce, along with sides such as bacon-black truffle macaroni and cheese.
Spend the night at Heaven’s Valley Lodge, a 200-acre working farm that rents a two-bedroom barn with a kitchen. Pick organic vegetables and fruit, sample fresh honey and collect fresh eggs for breakfast.
Or opt to sleep in town at Alexander Mansion Historic Bed and Breakfast, where CD players hide in phonographs and the innkeepers make amazing frittatas.
Head south of Winona about 12 miles to Great River Bluff State Park for scenic hikes along wooded bluffs above the Mississippi River. Wildflowers dot this 3,067-acre park each spring, with maples and basswoods blazing into color each fall.
Head back to town for healthy soups, creative sandwiches and quiches at the Blue Heron Coffeehouse. The food alone—especially for vegetarians—is worth a visit, but you can also browse the attached bookstore for a good read. Grab a sweetly glazed cardamom scone for later.
Lake Winona, and Sugar Loaf bluff in the distance, makes a great spot for a leisurely afternoon of reading, strolling the pathways or paddling a rented kayak.
Join the locals for a classic summer meal: homemade root beer, elk or bison burgers, and crispy sweet potato fries at the nostalgic Lakeview Drive Inn. If you visit on a Wednesday, close to 100 classic cars fill the lot and keep the carhops hopping.
More information: Visit Winona, (507) 454-4020; visitwinona.com