Start from 24 curated places around Winona, MN, then choose the recommendations that fit your guests.
Restaurants & cafés
Nosh Scratch Kitchen
The most ambitious restaurant in Winona and the one most likely to surprise visitors expecting a small-town dining scene. The kitchen works with Mediterranean influences and the produce and proteins of southeastern Minnesota and western Wisconsin farms, turning out dishes that Explore Minnesota compares favorably to the best of the Twin Cities. The cocktail program and wine list are both considered unusually well-curated for the market.
Bloedow Bakery
A family bakery on East Broadway that has been making donuts, rolls, breads, and cookies from the same recipes since 1924. Nationally recognized for its handmade donuts, the shop is small and the cases empty as the morning progresses — this is a place that rewards early arrivals. Everything is made by hand on the premises each morning.
Trails & outdoors
Sugar Loaf Bluff
The signature trail in Winona: a 1.3-mile out-and-back that climbs 374 feet to the base of the rock pinnacle with views over the city and Mississippi River valley. The trail is rocky and sandy in places with a brief section along a steep drop-off — more challenging than the short distance suggests. The payoff at the top is genuine.
Lake Winona Bike Path
A 5-mile paved loop that circles Lake Winona along a wide, mostly flat asphalt path — the most accessible walk or run in the city. The route gives views of Sugar Loaf and the southern bluffs from the lakeside and passes through neighborhoods, parks, and open shoreline. Good for families with strollers, cyclists, joggers, and anyone who wants a low-intensity scenic loop.
Things to do
Minnesota Marine Art Museum
The most surprising cultural institution between the Twin Cities and Chicago: a seven-acre riverside art museum with a permanent collection that includes Monet, Van Gogh, Homer, and Picasso alongside American maritime painters and contemporary water-themed work. The outdoor riverwalk and prairie garden are free to all. The museum runs a strong programming calendar of temporary exhibitions, lectures, and events throughout the year.
Great River Shakespeare Festival
A professional equity theater company that has been producing two simultaneous Shakespeare productions each summer since 2004, now performing at The ARC — the revived Historic Masonic Theatre at 255 Main Street in downtown Winona. Annual audiences exceed 10,000 and the acting company draws talent from across the country. The festival runs roughly four weeks in late June and July and is genuinely one of the best Shakespeare companies in the upper Midwest.
Landmarks & sights
Sugar Loaf
A rocky granite pinnacle rising above the south side of the city, shaped by 19th-century quarrying into the distinctive spire that now serves as Winona's skyline anchor. The short but steep trail to the base of the pinnacle delivers views over the city, Lake Winona, and the Mississippi River valley into Wisconsin. A defining image of the town that rewards the effort to actually climb it.
Minnesota Marine Art Museum
A serious art museum built on the west bank of the Mississippi, with six galleries holding a surprising permanent collection that includes works by Monet, Van Gogh, Picasso, and Winslow Homer alongside major American marine painters. The seven-acre riverside campus includes a cafe, a prairie garden, and direct views of the river — the kind of institution that earns repeat visits as the collection rotates.