Known for its historic architecture, Winona’s charming downtown is rife with opportunities for exploration.

Image by Todd Buchanan/Greenspring Media

Winona might surprise you. Once known primarily as a college town, the bluff country community is now a destination chock-full of historic charm, natural beauty and cultural hallmarks.

From the Twin Cities, head southeast and travel for about two hours along the Mississippi River (we recommend traveling by the Great River Road National Scenic Byway for exceptional scenery along the way). As you arrive in Winona, you’ll see how this river town is nestled within towering bluffs, almost like a waterfront scene from J.R.R. Tolkien’s Shire.

Minnesota Marine Art Museum

Image by wck/flickr

For a little pick-me-up, stop at Blue Heron Coffeehouse for carefully crafted coffee and espresso beverages, as well as vegetarian-friendly breakfast and lunch made from organic, locally sourced ingredients. While you’re in the area, stop by the Mid West Music Store, an offshoot of the city’s annual Mid West Music Fest every April.

Fully fueled, head to Riverview Drive to see priceless works of art at the Minnesota Marine Art Museum, which houses works by Picasso, Van Gogh, Renoir and Matisse alongside local folk art depicting maritime scenes. The collection also features the famed historic painting, “Washington Crossing the Delaware.” Admission is $7 for adults, $3 for students (free on Tuesdays) and free for children ages 4 and under.

For lunch, head down the river to the recently renovated Boat House Restaurant, situated across from the scenic Latsch Island at Levee Park. Its menu features bistro offerings such as steak frites, poutine and salmon niçoise salad, alongside dishes that wink to local heritage. Try the Boat House Lucy, which is filled with cheese curds in lieu of American cheese. There’s also a decent selection of craft beer, wine and cocktails, including “The Up North”—a blend of bourbon sweetened with maple syrup that comes garnished with two hearty strips of bacon.

Lake Winona

Afterward, continue your cultural exploration of Winona with Trester Trolley Tours. Clarence Russell, a longtime Winona resident, offers year-round tours of the city via a refurbished trolley. Learn about Winona’s storied past and see historic architecture, including the Basilica of Saint Stanislaus Kostka to the stunning views of the Garvin Heights Overlook.

If weather permits, spend some time outdoors in the midst of Winona’s inspiring landscape. Lake Park surrounds Lake Winona and features walking and biking trails, picnic sites, a rose garden with a gazebo and more. Hit the blacktop on foot or by bike for a five-mile outdoor excursion around the lake. For varied terrain, explore Holzinger Lodge Trail, a nine-mile, singletrack loop that winds around the bluffs overlooking Lake Winona. The trail is perfect for hiking and mountain biking.

When your adventuring leaves you famished, head to Signatures Restaurant for dinner. Located on the Bridges Golf Club grounds, Winona’s first fine-dining restaurant features an American surf ’n’ turf menu made with ingredients from local farms. We recommend trying a custom chef’s tasting menu, which comes with optional wine pairings and three perfectly seasoned, tender meat dishes: pan-seared duck breast, wood-smoked salmon and marinated sirloin, each paired with roasted root vegetables, as well as a delectable dessert.


Basilica of Saint Stanislaus Kostka

End the day at Ed’s (no name) Bar for a nightcap and live music. The quirky bar, founded by Boat House co-owner and artist Ed Hoffman, features a great selection of beers on tap, including Minnesota’s own Grain Belt, Summit, Fulton and Bent Paddle, plus wines and cocktails. Be sure to check out the unconventional artwork by Hoffman and other area artists that crowds the walls of the bar.

For a place to rest your head at night, look no further than Winona’s charming bed and breakfasts. The Carriage House Bed and Breakfast is located behind an 1870-era Victorian mansion that once belonged to lumber baron Conrad Bohn. Wake up to a delicious home-cooked egg soufflé with grilled sausage, potatoes and diced red peppers. Kick it up a notch at the luxurious Alexander Mansion Bed and Breakfast, a turn-of-the-century Victorian mansion that features five guest accommodations with period antiques and tasteful décor. In the morning you will be treated to a gourmet four-course breakfast, including a lightly spiced mix of fruit, a pastry, savory vegetable frittata or quiche, and a sweet ending in the form of vanilla ice cream sprinkled with cinnamon.

With so many sites and attractions to take in, Winona might be a town you have to visit many times.

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