Winona, MN

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.

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.

A corner cafe in Historic Downtown with original checkered tile floors, powder-blue walls, and a bookshelf nook that has been drawing students and locals since 1998. The kitchen uses organic and locally sourced ingredients for breakfast and lunch: specialty sandwiches, soups, and salads alongside genuinely good espresso. One of the most consistently reviewed restaurants in Winona.

Winona's oldest restaurant, a drive-in on the Lake Winona shore that has been operating since 1938 without shortcuts: every item made to order, nothing from a heat lamp or microwave. The menu runs to burgers, root beer floats, and classic summer drive-in food. The house-recipe root beer is made from scratch on site. A genuine piece of Americana that still works.

A lunch counter deli operating out of the historic old city hall building with a 30-year following for its oversized hoagie sandwiches and rotating daily soups. The Tuesday Wisconsin Cheese Soup — a thick, creamy base full of chunky melted cheese curds — has its own regional reputation. A fast, affordable, and genuinely satisfying lunch option for anyone spending the day in Historic Downtown.

A lively Mexican restaurant on the west side of Winona with a full bar, patio seating, and a menu that runs from enchiladas and street tacos to specialty tequila cocktails. The margaritas are made with fresh citrus and the kitchen handles a busy room efficiently. A reliable dinner option when the Historic Downtown places are full or you want something reliably satisfying after a day on the trails.

A family-run Northern Vietnamese bistro operated by first-generation Vietnamese-American owners, serving traditional pho, banh mi, and boba teas alongside a lineup of creative specialty drinks in a town where this kind of cooking was largely absent before they opened. The execution is careful and the quality control is consistent — both the food and the drink menu reward exploration.

The museum's in-house cafe occupies a corner of the riverside campus with views out to the Mississippi. It serves light lunches, coffee, and provisions during museum hours and doubles as a quiet spot to decompress mid-visit or after walking the prairie riverwalk trail. Not a destination meal in itself but one of the better positioned lunch breaks in Winona.

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.

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.

A 2.4-mile out-and-back trail that links Sugar Loaf with Garvin Heights Park, climbing through steep mixed hardwood forest with 662 feet of total elevation gain for both summits. The toughest walk available in the immediate city area and the one that delivers the most dramatic views — the Garvin Heights overlook, reached from below rather than by car, has a different quality than the drive-up version.

The most-reviewed trail in Great River Bluffs State Park, 13 miles southeast of Winona on the Great River Road: an easy 2.5-mile out-and-back to a bluff-top overlook of the Mississippi River valley through a native-species prairie and open goat-prairie ecosystem. The panoramic view at the end faces west across the valley and is considered one of the finest in Minnesota bluff country.

A 3.3-mile loop trail through Bluffside Park on the west end of the city, climbing through mature hardwood forest with short steep pitches and valley views. The trail is more demanding than its length suggests and is popular with local mountain bikers as well as hikers; weekday mornings offer the quietest experience. Fall foliage in October is the peak season.

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.

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.

An unusually substantial county history museum in a 1915 armory with a Joan Soranno-designed contemporary addition, covering the full arc of Winona County history from the river's Dakota-era culture through the Victorian lumber and grain-milling boom to the industrial 20th century. The exhibit on the stained glass industry and the walking tour maps for the city are available here and are the best single resource for independent exploration.

A three-week summer classical music festival running late June through mid-July in Winona, featuring world-class soloists and ensembles in a mix of indoor venues and an outdoor bandshell. The festival has built a national reputation in chamber music circles and draws performers who are genuinely sought-after at the major summer classical festivals. One of Minnesota's most distinctive cultural events.

The self-guided Glorious Glass Tour through Historic Downtown Winona leads walkers to the city's most significant stained glass sites — churches, civic buildings, and galleries produced by studios including Tiffany, Willet, and local Winona artists. The concentration of historic glass here is unlike anywhere else in the country and the tour is an hour well spent for anyone with an interest in decorative arts or architecture.

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.

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.

A hilltop park 575 feet above the Mississippi, reached by a short drive up from the Sugar Loaf area, with a paved overlook platform and picnic tables at the top. The view extends 20 to 30 miles up and down the river valley and takes in Latsch Island, the downtown, and the bluffs of Wisconsin across the river — one of the great free vantage points in Minnesota bluff country. Accessible for visitors who cannot hike Sugar Loaf.

A Mississippi River island directly across the main channel from downtown, home to Winona's marina and an unusual community of floating homes moored along its eastern shore. The island is connected to the mainland by a bridge and accessible by foot or bike; walking the perimeter levee trail reveals the river up close and the floating home neighborhood, which has no equivalent elsewhere in the region.

Housed in a 1915 National Guard Armory with a contemporary addition designed by celebrated Minnesota architect Joan Soranno, this museum tells the story of Winona County from its Dakota and Ho-Chunk roots through the lumber and grain-milling boom years to the present. The stained glass collection on display inside reflects the city's outsized role as a national center of the craft. More substantial than a small-town history museum typically is.

Winona has been called the stained glass capital of the United States, and the title holds: the city is home to more than half a dozen studios and dozens of historic church windows made by nationally significant craftspeople including Tiffany and the Willet studios, whose work has been installed in the National Cathedral in Washington, D.C. The self-guided Glorious Glass Tour map takes walkers to the highest concentrations in the historic downtown.