Winding Down in Winona

Take a trip to this river town and discover stunning architecture, buzzing coffee shops, gorgeous bluffs, and a thriving cultural scene.

  • Winona, Minnesota
    Photo courtesy of Explore Minnesota Tourism
    Winona’s fall colors
  • Winona, Minnesota
    Photo by Kirk Fratzke
    Minnesota Orchestra at the Beethoven Festival
  • Winona County History Center
    Photo courtesy of
    Winona County History Center
  • Winona, Minnesota
    Photo courtesy of
    Downtown Winona
  • Winona, Minnesota
    Photo coutesy of
    A sculpture by local artist Leo Smith
  • Village House Inn
    Photo courtesy of
    Village House Inn
  • Lake Winona
    Photo courtesy of Explore Minnesota Tourism
    Biking along Lake Winona
  • Winona, Minnesota
    Photo courtesy of
    Lakeview Drive Inn serves burgers, mahi mahi, and more

If only Matilda Jane DeBow Stevens could see Winona now. Her unsmiling photo, preserved in the Winona County History Center, is all that remains of the town's first white settler. She landed among the Dakotas in 1838 and bid adieu the very next year. Thirteen years later, a steamboat captain put down stakes and had better luck.

By 1852 the town had grown to 300 citizens. The newcomers flourished so well on this sandbar "island" on the Mississippi that a treaty was negotiated, which sent the Dakotas farther west to the Minnesota River. Wheat and lumber fueled the golden years of 1870 to 1890—years personified by the world-class architecture on Third Street.

Now, as then, wonders both manmade and natural lure visitors to this lovely river town. There are the historic brick and stone buildings, a robust cultural vibe underscored by three colleges, and the beauty of forested bluffs towering over the mighty river.



Topping the list of manmade wonders is the spice empire built by J.R. Watkins. You can spot the white Watkins tower from anywhere in town. Tour the shop and museum to find out about the year-by-year expansion of the company's line of products—from early ointments and complexion powders to chewing gum and coffee. And, of course, all those exotic flavorings salesmen once peddled house-to-house in horse-drawn carts.

After hitting the Watkins Museum, it's fun to spend a night at the Alexander Mansion Historic B&B—a Queen Anne extravaganza with ties to the Watkins family. Enjoy Watkins scented salts in the marble bathrooms and Watkins cinnamon in the breakfast coffeecake.

The influence of the Watkins family can be seen throughout town. Watkins's son-in-law became president of Winona National Bank and had a grand Egyptian Revival building built for it downtown in 1914. He called on Tiffany to fashion its marvelous stained-glass windows. Not to be outdone, rival Merchants Bank also boasts incredible stained glass in its massive, muscular Prairie-style edifice. Designed by Purcell & Elmslie in the style of their mentor, Frank Lloyd Wright, this architectural gem also boasts a shining 1915 mural of the city behind the tellers' desks.

Continue down Third Street on a self-guided tour (a phone app is available entitled Stories in Structure: Winona Architecture Tour) of the seven-block stretch preserved on the National Historic Register, and you'll find more architectural gems: Italianate columns, Queen Anne curlicues, and even an example of sturdy Romanesque Revival that makes the city waterworks look like a lord's castle.

The History Center, lodged in the brick armory of 1915, is loaded with local artifacts ranging from a Native American teepee to Watkins's daughter's fancy carriage. A timeline weaves visitors through intricate Dakota bead and quill embroidery, Civil War regalia, a wooden "Lincoln voting box," relics of the Roaring Twenties from "the wettest town in the Northwest," and a barbershop circa World War II, complete with blackout instructions.

Folks from as far away as Poland heard there were jobs here in the land of wheat and lumber and arrived, 6,000 strong, in the 1880s. There's a sprawling Polish Cultural Institute & Museum to prove it, with displays of treasures transported from the old country: intricate embroidered waistcoats, wedding dresses, china dolls with eyes as blue as robins' eggs, and the darker blue of Poland's signature pottery, which you can buy in the gift shop.

But the museum the city is most proud to showcase is the Minnesota Marine Art Museum, which anchors a pretty terrace on the riverfront and shows works such as Dutch and American paintings of ships and their captains, the dreamy landscapes of the Hudson River Valley painters, and a permanent collection, unique in a town of 28,000, that travels from Renoir and Monet to Van Gogh and O'Keeffe. At the gift shop you can buy the contemporary folk artworks of regional artisan Leo Smith.

To see what attracted so many people to this spot, stroll the river's levee, counting soaring eagles and low-slung barges churning down the river. And don't forget to explore the endless park bordering the city's other watery idol, Lake Winona. Rock in the romantic swings for two, catch a free concert at the band shell, or head to the lodge for free rental of canoes and bikes or, in wintertime, snowshoes and skates.



You can find more art and beauty at Winona State University, a garden-filled, stroll-worthy campus, but the university's biggest cultural attraction is the annual Great River Shakespeare Festival. Running every June through August, it draws talent from across the nation who stage a couple of the Bard's plays and host related public events including cocktail gatherings, garden tours, symposia, and more.

Another lovely campus, Saint Mary's University is home to an annual Beethoven Festival in July that attracts talent such as Branford Marsalis, Sharon Isbin, and Osmo Vänskä as well as many illustrious European chamber groups. Saint Mary's main parking lot is also the takeoff point for eight miles of wooded trails popular year-round.

Across the road, Village House Inn is an inn built with local brick and run by innkeeper Anne Larson, who moved here nine years ago, lured by the rolling hills (she's from South Dakota) and the town's rich lode of arts. Richard Grabow, who runs the Alexander Mansion Historic B&B, also appreciates the town's cultural, college-y vibe. "I can stop at the coffeehouse or bookstore and find a conversation with like-minded people," he says. One of those bookstores adjoins sweet little Blue Heron Coffehouse, home of lattes and healthy, fresh eats such as the best-selling egg salad sandwich and a Greek salad blooming with the white and purple of feta and olives.

For dinner, Grabow steers (and often drives) his guests to Signatures, nestled on a golf course hidden among the firs of the forest. The place is named for its owners' collection of items and autographs worthy of a Sotheby's auction, including Fred Astaire's umbrella, Bill Clinton's saxophone, Bob Dylan's harmonica, and signed album covers by the likes of The Beatles and Jerry Lee Lewis. The menu features locally sourced and creatively conceived wonders such as walleye cakes plumped with wild rice and sweet corn with roasted red pepper-truffle aioli, mussels in garlic and white wine topped with fresh herbs, and roast duck nested on a bed of roasted Brussels sprouts and a side of taleggio-filled nectarine.

Prefer dining in your jeans? Jefferson Pub & Grill, rising from the levee, is the answer. What to drink? A brandy old-fashioned, instructs the host, because Wisconsin just across the river is home to our nation's biggest brandy fans. Have a burger, a garlic steak, or the kitchen's famous black and blue quesadilla, starring blackened chicken and blue cheese.

Winona's oldest dining spot is the classic Lakeview Drive Inn, hauling victuals to your car ("Blink your lights") or umbrella table since 1938. Prices haven't changed too much since then—three bucks buys you a burger and fries. But menu options have kept up with the times: You'll finda tasty bison burger, sweet potato fries, and a grilled mahi mahi sandwich among the chicken baskets. Don't miss the homemade root beer.



Lake Park Lodge


Winona Visitors Center
924 Huff St. at Hwy. 61, 507-452-0735